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Номер 4, страница 226 - гдз по химии 10 класс учебник Еремин, Кузьменко
Авторы: Еремин В. В., Кузьменко Н. Е., Теренин В. И., Дроздов А. А., Лунин В. В.
Тип: Учебник
Издательство: Просвещение
Год издания: 2023 - 2026
Уровень обучения: углублённый
Цвет обложки: белый, зелёный с радугой
Допущено Министерством просвещения Российской Федерации
Популярные ГДЗ в 10 классе
Глава 3. Углеводороды. Параграф 42. Галогенопроизводные углеводородов - номер 4, страница 226.
App\Models\Task {#1030 // resources/views/models/task/default.blade.php #connection: "mysql" #table: "tasks" #primaryKey: "id" #keyType: "int" +incrementing: true #with: [] #withCount: [] +preventsLazyLoading: false #perPage: 15 +exists: true +wasRecentlyCreated: false #escapeWhenCastingToString: false #attributes: array:24 [ "id" => 663193 "created_at" => "2026-04-10 13:58:26" "updated_at" => null "field_page_start" => "226" "field_page_end" => null "field_url" => "/10-klass/himiya/eremin-uchebnik/42-4" "field_display_title" => "4" "field_outside_task" => null "field_task_type" => Illuminate\Database\Eloquent\Collection {#1037 #items: array:1 [ 0 => App\Models\Term {#1036 #connection: "mysql" #table: "terms" #primaryKey: "id" #keyType: "int" +incrementing: false #with: [] #withCount: [] +preventsLazyLoading: false #perPage: 15 +exists: true +wasRecentlyCreated: false #escapeWhenCastingToString: false #attributes: array:6 [ "id" => 26 "created_at" => "2026-04-10 13:58:26" "updated_at" => null "name" => "номер" "field_cases" => array:6 [ "field_accusative_case" => "номер" "field_creative_case" => "номером" "field_dative_case" => "номеру" "field_genitive_case" => "номера" "field_nominative_case" => "номер" "field_prepositional_case" => "номере" ] "field_short_name" => "№" ] #original: array:6 [ "id" => 26 "created_at" => "2026-04-10 13:58:26" "updated_at" => null "name" => "номер" "field_cases" => array:6 [ "field_accusative_case" => "номер" "field_creative_case" => "номером" "field_dative_case" => "номеру" "field_genitive_case" => "номера" "field_nominative_case" => "номер" "field_prepositional_case" => "номере" ] "field_short_name" => "№" ] #changes: [] #casts: [] #classCastCache: [] #attributeCastCache: [] #dateFormat: null #appends: [] #dispatchesEvents: [] #observables: [] #relations: [] #touches: [] +timestamps: true +usesUniqueIds: false #hidden: [] #visible: [] #fillable: [] #guarded: array:1 [ 0 => "*" ] } ] #escapeWhenCastingToString: false } "field_metatags_title" => null "field_metatags_description" => null "field_h1" => null "field_description_top" => null "field_description_bottom" => null "field_match" => null "breadcrumbs" => [] "edition_groups" => Illuminate\Database\Eloquent\Collection {#1035 #items: [] #escapeWhenCastingToString: false } "top_parent_branch" => Illuminate\Database\Eloquent\Collection {#1079 #items: array:1 [ 0 => App\Models\Branch {#1034 #connection: "mysql" #table: "branches" #primaryKey: "id" #keyType: "int" +incrementing: true #with: [] #withCount: [] +preventsLazyLoading: false #perPage: 15 +exists: true +wasRecentlyCreated: false #escapeWhenCastingToString: false #attributes: array:24 [ "id" => 662723 "created_at" => "2026-04-10 13:58:26" "updated_at" => null "field_display_title" => "Углеводороды" "field_branch_order" => "3" "field_url" => null "field_branch_type" => Illuminate\Database\Eloquent\Collection {#1039 #items: array:1 [ 0 => App\Models\Term {#1038 #connection: "mysql" #table: "terms" #primaryKey: "id" #keyType: "int" +incrementing: false #with: [] #withCount: [] +preventsLazyLoading: false #perPage: 15 +exists: true +wasRecentlyCreated: false #escapeWhenCastingToString: false #attributes: array:7 [ "id" => 29 "created_at" => "2026-04-10 13:58:26" "updated_at" => null "name" => "Глава" "field_cases" => array:6 [ …6] "field_page_check_not_needed" => null "field_short_name" => null ] #original: array:7 [ "id" => 29 "created_at" => "2026-04-10 13:58:26" "updated_at" => null "name" => "Глава" "field_cases" => array:6 [ …6] "field_page_check_not_needed" => null "field_short_name" => null ] #changes: [] #casts: [] #classCastCache: [] #attributeCastCache: [] #dateFormat: null #appends: [] #dispatchesEvents: [] #observables: [] #relations: [] #touches: [] +timestamps: true +usesUniqueIds: false #hidden: [] #visible: [] #fillable: [] #guarded: array:1 [ 0 => "*" ] } ] #escapeWhenCastingToString: false } "field_page_start" => "139" "field_branch_display" => "0" "field_branch_expanded" => "0" "field_display_branch_in_title" => "1" "field_display_task_interval" => "0" "field_display_branch_page" => "1" "field_branch_title_in_content" => "0" "field_navigation_title" => null "field_metatags_title" => null "field_metatags_description" => null "field_h1" => null "field_description_top" => null "field_description_bottom" => null "field_branch_cover" => [] "field_branch_covers" => [] "book" => Illuminate\Database\Eloquent\Collection {#1040 #items: array:1 [ 0 => App\Models\Book {#1041 #connection: "mysql" #table: "books" #primaryKey: "id" #keyType: "int" +incrementing: false #with: [] #withCount: [] +preventsLazyLoading: false #perPage: 15 +exists: true +wasRecentlyCreated: false #escapeWhenCastingToString: false #attributes: array:50 [ "id" => 1003 "created_at" => "2026-04-10 13:58:26" "updated_at" => null "field_tree_default_status" => "tasks" "field_pages_status" => null "field_subject" => Illuminate\Database\Eloquent\Collection {#1042 …2} "field_class" => Illuminate\Database\Eloquent\Collection {#1044 …2} "field_publisher" => Illuminate\Database\Eloquent\Collection {#1046 …2} "field_author" => Illuminate\Database\Eloquent\Collection {#1048 …2} "field_author_foreign" => Illuminate\Database\Eloquent\Collection {#1054 …2} "field_book_type" => Illuminate\Database\Eloquent\Collection {#1055 …2} "field_country" => Illuminate\Database\Eloquent\Collection {#1057 …2} "field_city" => Illuminate\Database\Eloquent\Collection {#1059 …2} "field_series" => Illuminate\Database\Eloquent\Collection {#1061 …2} "field_umk" => Illuminate\Database\Eloquent\Collection {#1062 …2} "field_level_of_education" => Illuminate\Database\Eloquent\Collection {#1063 …2} "field_standart_of_education" => Illuminate\Database\Eloquent\Collection {#1065 …2} "field_publication_number" => "10" "field_publication_type" => Illuminate\Database\Eloquent\Collection {#1067 …2} "field_under_the_edition" => Illuminate\Database\Eloquent\Collection {#1069 …2} "field_under_the_edition_degree" => "доктор химических наук, академика РАН" "field_cover_description" => "с радугой" "field_publication_year" => "2023" "field_publication_year_until" => null "field_part" => "" "field_part_writing" => "" "field_second_foreign_language" => null "field_for_whom" => null "field_allowed" => "Допущено Министерством просвещения Российской Федерации" "field_reserve_field" => null "field_link_to_source" => null "field_tasks_count" => "697" "field_priority" => "10" "field_default_folder" => "/himiya_10/eremin-u23/" "field_isbn" => null "field_cover" => array:1 [ …1] "field_cover_alts" => array:1 [ …1] "field_covers" => array:1 [ …1] "field_popular_book" => null "field_recommended_books" => Illuminate\Database\Eloquent\Collection {#1070 …2} "field_new_book" => Illuminate\Database\Eloquent\Collection {#1071 …2} "field_old_book" => Illuminate\Database\Eloquent\Collection {#1072 …2} "field_url" => "/10-klass/himiya/eremin-uchebnik" "field_cover_color" => Illuminate\Database\Eloquent\Collection {#1073 …2} "field_metatags_title" => null "field_metatags_description" => null "field_h1" => null "field_description_top" => null "field_description_bottom" => null "breadcrumbs" => array:3 [ …3] ] #original: array:50 [ "id" => 1003 "created_at" => "2026-04-10 13:58:26" "updated_at" => null "field_tree_default_status" => "tasks" "field_pages_status" => null "field_subject" => Illuminate\Database\Eloquent\Collection {#1042 …2} "field_class" => Illuminate\Database\Eloquent\Collection {#1044 …2} "field_publisher" => Illuminate\Database\Eloquent\Collection {#1046 …2} "field_author" => Illuminate\Database\Eloquent\Collection {#1048 …2} "field_author_foreign" => Illuminate\Database\Eloquent\Collection {#1054 …2} "field_book_type" => Illuminate\Database\Eloquent\Collection {#1055 …2} "field_country" => Illuminate\Database\Eloquent\Collection {#1057 …2} "field_city" => Illuminate\Database\Eloquent\Collection {#1059 …2} "field_series" => Illuminate\Database\Eloquent\Collection {#1061 …2} "field_umk" => Illuminate\Database\Eloquent\Collection {#1062 …2} "field_level_of_education" => Illuminate\Database\Eloquent\Collection {#1063 …2} "field_standart_of_education" => Illuminate\Database\Eloquent\Collection {#1065 …2} "field_publication_number" => "10" "field_publication_type" => Illuminate\Database\Eloquent\Collection {#1067 …2} "field_under_the_edition" => Illuminate\Database\Eloquent\Collection {#1069 …2} "field_under_the_edition_degree" => "доктор химических наук, академика РАН" "field_cover_description" => "с радугой" "field_publication_year" => "2023" "field_publication_year_until" => null "field_part" => "" "field_part_writing" => "" "field_second_foreign_language" => null "field_for_whom" => null "field_allowed" => "Допущено Министерством просвещения Российской Федерации" "field_reserve_field" => null "field_link_to_source" => null "field_tasks_count" => "697" "field_priority" => "10" "field_default_folder" => "/himiya_10/eremin-u23/" "field_isbn" => null "field_cover" => array:1 [ …1] "field_cover_alts" => array:1 [ …1] "field_covers" => array:1 [ …1] "field_popular_book" => null "field_recommended_books" => Illuminate\Database\Eloquent\Collection {#1070 …2} "field_new_book" => Illuminate\Database\Eloquent\Collection {#1071 …2} "field_old_book" => Illuminate\Database\Eloquent\Collection {#1072 …2} "field_url" => "/10-klass/himiya/eremin-uchebnik" "field_cover_color" => Illuminate\Database\Eloquent\Collection {#1073 …2} "field_metatags_title" => null "field_metatags_description" => null "field_h1" => null "field_description_top" => null "field_description_bottom" => null "breadcrumbs" => array:3 [ …3] ] #changes: [] #casts: [] #classCastCache: [] #attributeCastCache: [] #dateFormat: null #appends: [] #dispatchesEvents: [] #observables: [] #relations: [] #touches: [] +timestamps: true +usesUniqueIds: false #hidden: [] #visible: [] #fillable: [] #guarded: array:1 [ 0 => "*" ] } ] #escapeWhenCastingToString: false } "branch_parent" => Illuminate\Database\Eloquent\Collection {#1076 #items: [] #escapeWhenCastingToString: false } ] #original: array:24 [ "id" => 662723 "created_at" => "2026-04-10 13:58:26" "updated_at" => null "field_display_title" => "Углеводороды" "field_branch_order" => "3" "field_url" => null "field_branch_type" => Illuminate\Database\Eloquent\Collection {#1039} "field_page_start" => "139" "field_branch_display" => "0" "field_branch_expanded" => "0" "field_display_branch_in_title" => "1" "field_display_task_interval" => "0" "field_display_branch_page" => "1" "field_branch_title_in_content" => "0" "field_navigation_title" => null "field_metatags_title" => null "field_metatags_description" => null "field_h1" => null "field_description_top" => null "field_description_bottom" => null "field_branch_cover" => [] "field_branch_covers" => [] "book" => Illuminate\Database\Eloquent\Collection {#1040} "branch_parent" => Illuminate\Database\Eloquent\Collection {#1076} ] #changes: [] #casts: [] #classCastCache: [] #attributeCastCache: [] #dateFormat: null #appends: [] #dispatchesEvents: [] #observables: [] #relations: [] #touches: [] +timestamps: true +usesUniqueIds: false #hidden: [] #visible: [] #fillable: [] #guarded: array:1 [ 0 => "*" ] } ] #escapeWhenCastingToString: false } "parent_branches" => Illuminate\Database\Eloquent\Collection {#1120 #items: array:2 [ 0 => App\Models\Branch {#1128 #connection: "mysql" #table: "branches" #primaryKey: "id" #keyType: "int" +incrementing: true #with: [] #withCount: [] +preventsLazyLoading: false #perPage: 15 +exists: true +wasRecentlyCreated: false #escapeWhenCastingToString: false #attributes: array:24 [ "id" => 662723 "created_at" => "2026-04-10 13:58:26" "updated_at" => null "field_display_title" => "Углеводороды" "field_branch_order" => "3" "field_url" => null "field_branch_type" => Illuminate\Database\Eloquent\Collection {#1132 #items: array:1 [ 0 => App\Models\Term {#1129 #connection: "mysql" #table: "terms" #primaryKey: "id" #keyType: "int" +incrementing: false #with: [] #withCount: [] +preventsLazyLoading: false #perPage: 15 +exists: true +wasRecentlyCreated: false #escapeWhenCastingToString: false #attributes: array:7 [ "id" => 29 "created_at" => "2026-04-10 13:58:26" "updated_at" => null "name" => "Глава" "field_cases" => array:6 [ …6] "field_page_check_not_needed" => null "field_short_name" => null ] #original: array:7 [ "id" => 29 "created_at" => "2026-04-10 13:58:26" "updated_at" => null "name" => "Глава" "field_cases" => array:6 [ …6] "field_page_check_not_needed" => null "field_short_name" => null ] #changes: [] #casts: [] #classCastCache: [] #attributeCastCache: [] #dateFormat: null #appends: [] #dispatchesEvents: [] #observables: [] #relations: [] #touches: [] +timestamps: true +usesUniqueIds: false #hidden: [] #visible: [] #fillable: [] #guarded: array:1 [ 0 => "*" ] } ] #escapeWhenCastingToString: false } "field_page_start" => "139" "field_branch_display" => "0" "field_branch_expanded" => "0" "field_display_branch_in_title" => "1" "field_display_task_interval" => "0" "field_display_branch_page" => "1" "field_branch_title_in_content" => "0" "field_navigation_title" => null "field_metatags_title" => null "field_metatags_description" => null "field_h1" => null "field_description_top" => null "field_description_bottom" => null "field_branch_cover" => [] "field_branch_covers" => [] "book" => Illuminate\Database\Eloquent\Collection {#1168 #items: array:1 [ 0 => App\Models\Book {#1131 #connection: "mysql" #table: "books" #primaryKey: "id" #keyType: "int" +incrementing: false #with: [] #withCount: [] +preventsLazyLoading: false #perPage: 15 +exists: true +wasRecentlyCreated: false #escapeWhenCastingToString: false #attributes: array:50 [ "id" => 1003 "created_at" => "2026-04-10 13:58:26" "updated_at" => null "field_tree_default_status" => "tasks" "field_pages_status" => null "field_subject" => Illuminate\Database\Eloquent\Collection {#1133 #items: array:1 [ 0 => App\Models\Term {#1130 #connection: "mysql" #table: "terms" #primaryKey: "id" #keyType: "int" +incrementing: false #with: [] #withCount: [] +preventsLazyLoading: false #perPage: 15 +exists: true +wasRecentlyCreated: false #escapeWhenCastingToString: false #attributes: array:10 [ "id" => 6495 "created_at" => "2026-04-10 13:58:26" "updated_at" => null "name" => "Химия" "field_abbreviated_name" => null "field_cases" => array:6 [ …6] "field_foreign_lang_name" => null "field_short_name" => null "field_subject_type" => "technical_subject" "field_translit" => "himiya" ] #original: array:10 [ "id" => 6495 "created_at" => "2026-04-10 13:58:26" "updated_at" => null "name" => "Химия" "field_abbreviated_name" => null "field_cases" => array:6 [ …6] "field_foreign_lang_name" => null "field_short_name" => null "field_subject_type" => "technical_subject" "field_translit" => "himiya" ] #changes: [] #casts: [] #classCastCache: [] #attributeCastCache: [] #dateFormat: null #appends: [] #dispatchesEvents: [] #observables: [] #relations: [] #touches: [] +timestamps: true +usesUniqueIds: false #hidden: [] #visible: [] #fillable: [] #guarded: array:1 [ 0 => "*" ] } ] #escapeWhenCastingToString: false } "field_class" => Illuminate\Database\Eloquent\Collection {#1134 #items: array:1 [ 0 => App\Models\Term {#1135 #connection: "mysql" #table: "terms" #primaryKey: "id" #keyType: "int" +incrementing: false #with: [] #withCount: [] +preventsLazyLoading: false #perPage: 15 +exists: true +wasRecentlyCreated: false #escapeWhenCastingToString: false #attributes: array:6 [ "id" => 5459 "created_at" => "2026-04-10 13:58:26" "updated_at" => null "name" => "10" "field_cases" => array:6 [ …6] "field_translit" => "desjatyj" ] #original: array:6 [ "id" => 5459 "created_at" => "2026-04-10 13:58:26" "updated_at" => null "name" => "10" "field_cases" => array:6 [ …6] "field_translit" => "desjatyj" ] #changes: [] #casts: [] #classCastCache: [] #attributeCastCache: [] #dateFormat: null #appends: [] #dispatchesEvents: [] #observables: [] #relations: [] #touches: [] +timestamps: true +usesUniqueIds: false #hidden: [] #visible: [] #fillable: [] #guarded: array:1 [ 0 => "*" ] } ] #escapeWhenCastingToString: false } "field_publisher" => Illuminate\Database\Eloquent\Collection {#1136 #items: array:1 [ 0 => App\Models\Term {#1137 #connection: "mysql" #table: "terms" #primaryKey: "id" #keyType: "int" +incrementing: false #with: [] #withCount: [] +preventsLazyLoading: false #perPage: 15 +exists: true +wasRecentlyCreated: false #escapeWhenCastingToString: false #attributes: array:6 [ "id" => 5153 "created_at" => "2026-04-10 13:58:26" "updated_at" => null "name" => "Просвещение" "field_cases" => null "field_translit" => "prosveschenie" ] #original: array:6 [ "id" => 5153 "created_at" => "2026-04-10 13:58:26" "updated_at" => null "name" => "Просвещение" "field_cases" => null "field_translit" => "prosveschenie" ] #changes: [] #casts: [] #classCastCache: [] #attributeCastCache: [] #dateFormat: null #appends: [] #dispatchesEvents: [] #observables: [] #relations: [] #touches: [] +timestamps: true +usesUniqueIds: false #hidden: [] #visible: [] #fillable: [] #guarded: array:1 [ 0 => "*" ] } ] #escapeWhenCastingToString: false } "field_author" => Illuminate\Database\Eloquent\Collection {#1138 #items: array:5 [ 0 => App\Models\Term {#1139 #connection: "mysql" #table: "terms" #primaryKey: "id" #keyType: "int" +incrementing: false #with: [] #withCount: [] +preventsLazyLoading: false #perPage: 15 +exists: true +wasRecentlyCreated: false #escapeWhenCastingToString: false #attributes: array:12 [ "id" => 4330 "created_at" => "2026-04-10 13:58:26" "updated_at" => null "name" => "Еремин" "field_bio" => null "field_degree_rp" => null "field_foreign_lang_name" => null "field_foreign_lang_patronymic" => null "field_foreign_lang_surname" => null "field_name" => "Вадим" "field_patronymic" => "Владимирович" "field_surname_rp" => null ] #original: array:12 [ "id" => 4330 "created_at" => "2026-04-10 13:58:26" "updated_at" => null "name" => "Еремин" "field_bio" => null "field_degree_rp" => null "field_foreign_lang_name" => null "field_foreign_lang_patronymic" => null "field_foreign_lang_surname" => null "field_name" => "Вадим" "field_patronymic" => "Владимирович" "field_surname_rp" => null ] #changes: [] #casts: [] #classCastCache: [] #attributeCastCache: [] #dateFormat: null #appends: [] #dispatchesEvents: [] #observables: [] #relations: [] #touches: [] +timestamps: true +usesUniqueIds: false #hidden: [] #visible: [] #fillable: [] #guarded: array:1 [ 0 => "*" ] } 1 => App\Models\Term {#1140 #connection: "mysql" #table: "terms" #primaryKey: "id" #keyType: "int" +incrementing: false #with: [] #withCount: [] +preventsLazyLoading: false #perPage: 15 +exists: true +wasRecentlyCreated: false #escapeWhenCastingToString: false #attributes: array:12 [ "id" => 4876 "created_at" => "2026-04-10 13:58:26" "updated_at" => null "name" => "Кузьменко" "field_bio" => null "field_degree_rp" => null "field_foreign_lang_name" => null "field_foreign_lang_patronymic" => null "field_foreign_lang_surname" => null "field_name" => "Николай" "field_patronymic" => "Егорович" "field_surname_rp" => null ] #original: array:12 [ "id" => 4876 "created_at" => "2026-04-10 13:58:26" "updated_at" => null "name" => "Кузьменко" "field_bio" => null "field_degree_rp" => null "field_foreign_lang_name" => null "field_foreign_lang_patronymic" => null "field_foreign_lang_surname" => null "field_name" => "Николай" "field_patronymic" => "Егорович" "field_surname_rp" => null ] #changes: [] #casts: [] #classCastCache: [] #attributeCastCache: [] #dateFormat: null #appends: [] #dispatchesEvents: [] #observables: [] #relations: [] #touches: [] +timestamps: true +usesUniqueIds: false #hidden: [] #visible: [] #fillable: [] #guarded: array:1 [ 0 => "*" ] } 2 => App\Models\Term {#1141 #connection: "mysql" #table: "terms" #primaryKey: "id" #keyType: "int" +incrementing: false #with: [] #withCount: [] +preventsLazyLoading: false #perPage: 15 +exists: true +wasRecentlyCreated: false #escapeWhenCastingToString: false #attributes: array:12 [ "id" => 5912 "created_at" => "2026-04-10 13:58:26" "updated_at" => null "name" => "Теренин" "field_bio" => null "field_degree_rp" => null "field_foreign_lang_name" => null "field_foreign_lang_patronymic" => null "field_foreign_lang_surname" => null "field_name" => "Владимир" "field_patronymic" => "Ильич" "field_surname_rp" => null ] #original: array:12 [ "id" => 5912 "created_at" => "2026-04-10 13:58:26" "updated_at" => null "name" => "Теренин" "field_bio" => null "field_degree_rp" => null "field_foreign_lang_name" => null "field_foreign_lang_patronymic" => null "field_foreign_lang_surname" => null "field_name" => "Владимир" "field_patronymic" => "Ильич" "field_surname_rp" => null ] #changes: [] #casts: [] #classCastCache: [] #attributeCastCache: [] #dateFormat: null #appends: [] #dispatchesEvents: [] #observables: [] #relations: [] #touches: [] +timestamps: true +usesUniqueIds: false #hidden: [] #visible: [] #fillable: [] #guarded: array:1 [ 0 => "*" ] } 3 => App\Models\Term {#1142 #connection: "mysql" #table: "terms" #primaryKey: "id" #keyType: "int" +incrementing: false #with: [] #withCount: [] +preventsLazyLoading: false #perPage: 15 +exists: true +wasRecentlyCreated: false #escapeWhenCastingToString: false #attributes: array:12 [ "id" => 4290 "created_at" => "2026-04-10 13:58:26" "updated_at" => null "name" => "Дроздов" "field_bio" => null "field_degree_rp" => null "field_foreign_lang_name" => null "field_foreign_lang_patronymic" => null "field_foreign_lang_surname" => null "field_name" => "Андрей" "field_patronymic" => "Анатольевич" "field_surname_rp" => null ] #original: array:12 [ "id" => 4290 "created_at" => "2026-04-10 13:58:26" "updated_at" => null "name" => "Дроздов" "field_bio" => null "field_degree_rp" => null "field_foreign_lang_name" => null "field_foreign_lang_patronymic" => null "field_foreign_lang_surname" => null "field_name" => "Андрей" "field_patronymic" => "Анатольевич" "field_surname_rp" => null ] #changes: [] #casts: [] #classCastCache: [] #attributeCastCache: [] #dateFormat: null #appends: [] #dispatchesEvents: [] #observables: [] #relations: [] #touches: [] +timestamps: true +usesUniqueIds: false #hidden: [] #visible: [] #fillable: [] #guarded: array:1 [ 0 => "*" ] } 4 => App\Models\Term {#1143 #connection: "mysql" #table: "terms" #primaryKey: "id" #keyType: "int" +incrementing: false #with: [] #withCount: [] +preventsLazyLoading: false #perPage: 15 +exists: true +wasRecentlyCreated: false #escapeWhenCastingToString: false #attributes: array:12 [ "id" => 5031 "created_at" => "2026-04-10 13:58:26" "updated_at" => null "name" => "Лунин" "field_bio" => null "field_degree_rp" => "доктор химических наук, академика РАН" "field_foreign_lang_name" => null "field_foreign_lang_patronymic" => null "field_foreign_lang_surname" => null "field_name" => "Валерий" "field_patronymic" => "Васильевич" "field_surname_rp" => "Лунина" ] #original: array:12 [ "id" => 5031 "created_at" => "2026-04-10 13:58:26" "updated_at" => null "name" => "Лунин" "field_bio" => null "field_degree_rp" => "доктор химических наук, академика РАН" "field_foreign_lang_name" => null "field_foreign_lang_patronymic" => null "field_foreign_lang_surname" => null "field_name" => "Валерий" "field_patronymic" => "Васильевич" "field_surname_rp" => "Лунина" ] #changes: [] #casts: [] #classCastCache: [] #attributeCastCache: [] #dateFormat: null #appends: [] #dispatchesEvents: [] #observables: [] #relations: [] #touches: [] +timestamps: true +usesUniqueIds: false #hidden: [] #visible: [] #fillable: [] #guarded: array:1 [ 0 => "*" ] } ] #escapeWhenCastingToString: false } "field_author_foreign" => Illuminate\Database\Eloquent\Collection {#1144 #items: [] #escapeWhenCastingToString: false } "field_book_type" => Illuminate\Database\Eloquent\Collection {#1145 #items: array:1 [ 0 => App\Models\Term {#1146 #connection: "mysql" #table: "terms" #primaryKey: "id" #keyType: "int" +incrementing: false #with: [] #withCount: [] +preventsLazyLoading: false #perPage: 15 +exists: true +wasRecentlyCreated: false #escapeWhenCastingToString: false #attributes: array:10 [ "id" => 6671 "created_at" => "2026-04-10 13:58:26" "updated_at" => null "name" => "Учебник" "field_book_type_foreign" => null "field_cases" => array:6 [ …6] "field_plural_form" => null "field_short_name" => null "field_short_name_foreign" => null "field_translit" => "uchebnik" ] #original: array:10 [ "id" => 6671 "created_at" => "2026-04-10 13:58:26" "updated_at" => null "name" => "Учебник" "field_book_type_foreign" => null "field_cases" => array:6 [ …6] "field_plural_form" => null "field_short_name" => null "field_short_name_foreign" => null "field_translit" => "uchebnik" ] #changes: [] #casts: [] #classCastCache: [] #attributeCastCache: [] #dateFormat: null #appends: [] #dispatchesEvents: [] #observables: [] #relations: [] #touches: [] +timestamps: true +usesUniqueIds: false #hidden: [] #visible: [] #fillable: [] #guarded: array:1 [ 0 => "*" ] } ] #escapeWhenCastingToString: false } "field_country" => Illuminate\Database\Eloquent\Collection {#1147 #items: array:1 [ 0 => App\Models\Term {#1148 #connection: "mysql" #table: "terms" #primaryKey: "id" #keyType: "int" +incrementing: false #with: [] #withCount: [] +preventsLazyLoading: false #perPage: 15 +exists: true +wasRecentlyCreated: false #escapeWhenCastingToString: false #attributes: array:6 [ "id" => 9 "created_at" => "2026-04-10 13:58:26" "updated_at" => null "name" => "Россия" "field_cases" => array:6 [ …6] "field_translit" => "rossiya" ] #original: array:6 [ "id" => 9 "created_at" => "2026-04-10 13:58:26" "updated_at" => null "name" => "Россия" "field_cases" => array:6 [ …6] "field_translit" => "rossiya" ] #changes: [] #casts: [] #classCastCache: [] #attributeCastCache: [] #dateFormat: null #appends: [] #dispatchesEvents: [] #observables: [] #relations: [] #touches: [] +timestamps: true +usesUniqueIds: false #hidden: [] #visible: [] #fillable: [] #guarded: array:1 [ 0 => "*" ] } ] #escapeWhenCastingToString: false } "field_city" => Illuminate\Database\Eloquent\Collection {#1149 #items: array:1 [ 0 => App\Models\Term {#1150 #connection: "mysql" #table: "terms" #primaryKey: "id" #keyType: "int" +incrementing: false #with: [] #withCount: [] +preventsLazyLoading: false #perPage: 15 +exists: true +wasRecentlyCreated: false #escapeWhenCastingToString: false #attributes: array:6 [ "id" => 15 "created_at" => "2026-04-10 13:58:26" "updated_at" => null "name" => "Москва" "field_cases" => array:6 [ …6] "field_translit" => "moskva" ] #original: array:6 [ "id" => 15 "created_at" => "2026-04-10 13:58:26" "updated_at" => null "name" => "Москва" "field_cases" => array:6 [ …6] "field_translit" => "moskva" ] #changes: [] #casts: [] #classCastCache: [] #attributeCastCache: [] #dateFormat: null #appends: [] #dispatchesEvents: [] #observables: [] #relations: [] #touches: [] +timestamps: true +usesUniqueIds: false #hidden: [] #visible: [] #fillable: [] #guarded: array:1 [ 0 => "*" ] } ] #escapeWhenCastingToString: false } "field_series" => Illuminate\Database\Eloquent\Collection {#1151 #items: [] #escapeWhenCastingToString: false } "field_umk" => Illuminate\Database\Eloquent\Collection {#1152 #items: [] #escapeWhenCastingToString: false } "field_level_of_education" => Illuminate\Database\Eloquent\Collection {#1153 #items: array:1 [ 0 => App\Models\Term {#1154 #connection: "mysql" #table: "terms" #primaryKey: "id" #keyType: "int" +incrementing: false #with: [] #withCount: [] +preventsLazyLoading: false #perPage: 15 +exists: true +wasRecentlyCreated: false #escapeWhenCastingToString: false #attributes: array:6 [ "id" => 39 "created_at" => "2026-04-10 13:58:26" "updated_at" => null "name" => "углублённый" "field_cases" => array:6 [ …6] "field_translit" => "uglublennyy" ] #original: array:6 [ "id" => 39 "created_at" => "2026-04-10 13:58:26" "updated_at" => null "name" => "углублённый" "field_cases" => array:6 [ …6] …1 ] #changes: [] #casts: [] #classCastCache: [] #attributeCastCache: [] #dateFormat: null #appends: [] #dispatchesEvents: [] #observables: [] #relations: [] #touches: [] +timestamps: true +usesUniqueIds: false #hidden: [] #visible: [] #fillable: [] #guarded: array:1 [ …1] } ] #escapeWhenCastingToString: false } "field_standart_of_education" => Illuminate\Database\Eloquent\Collection {#1155 #items: array:1 [ 0 => App\Models\Term {#1156 #connection: "mysql" #table: "terms" #primaryKey: "id" #keyType: "int" +incrementing: false #with: [] #withCount: [] +preventsLazyLoading: false #perPage: 15 +exists: true +wasRecentlyCreated: false #escapeWhenCastingToString: false #attributes: array:10 [ …10] #original: array:10 [ …10] #changes: [] #casts: [] #classCastCache: [] #attributeCastCache: [] #dateFormat: null #appends: [] #dispatchesEvents: [] #observables: [] #relations: [] #touches: [] +timestamps: true +usesUniqueIds: false #hidden: [] #visible: [] #fillable: [] #guarded: array:1 [ …1] } ] #escapeWhenCastingToString: false } "field_publication_number" => "10" "field_publication_type" => Illuminate\Database\Eloquent\Collection {#1157 #items: array:1 [ 0 => App\Models\Term {#1158 #connection: "mysql" #table: "terms" #primaryKey: "id" #keyType: "int" +incrementing: false #with: [] #withCount: [] +preventsLazyLoading: false #perPage: 15 +exists: true +wasRecentlyCreated: false #escapeWhenCastingToString: false #attributes: array:6 [ …6] #original: array:6 [ …6] #changes: [] #casts: [] #classCastCache: [] #attributeCastCache: [] #dateFormat: null #appends: [] #dispatchesEvents: [] #observables: [] #relations: [] #touches: [] +timestamps: true +usesUniqueIds: false #hidden: [] #visible: [] #fillable: [] #guarded: array:1 [ …1] } ] #escapeWhenCastingToString: false } "field_under_the_edition" => Illuminate\Database\Eloquent\Collection {#1159 #items: array:1 [ 0 => App\Models\Term {#1143} ] #escapeWhenCastingToString: false } "field_under_the_edition_degree" => "доктор химических наук, академика РАН" "field_cover_description" => "с радугой" "field_publication_year" => "2023" "field_publication_year_until" => null "field_part" => "" "field_part_writing" => "" "field_second_foreign_language" => null "field_for_whom" => null "field_allowed" => "Допущено Министерством просвещения Российской Федерации" "field_reserve_field" => null "field_link_to_source" => null "field_tasks_count" => "697" "field_priority" => "10" "field_default_folder" => "/himiya_10/eremin-u23/" "field_isbn" => null "field_cover" => array:1 [ 0 => "/media/himiya_10/eremin-u23/covers/cover1.webp?ts=1738768732" ] "field_cover_alts" => array:1 [ 0 => "" ] "field_covers" => array:1 [ 0 => array:4 [ "path" => "/media/himiya_10/eremin-u23/covers/cover1.webp?ts=1738768732" "alt" => "" "width" => "1200" "height" => "1576" ] ] "field_popular_book" => null "field_recommended_books" => Illuminate\Database\Eloquent\Collection {#1160 #items: [] #escapeWhenCastingToString: false } "field_new_book" => Illuminate\Database\Eloquent\Collection {#1161 #items: [] #escapeWhenCastingToString: false } "field_old_book" => Illuminate\Database\Eloquent\Collection {#1162 #items: [] #escapeWhenCastingToString: false } "field_url" => "/10-klass/himiya/eremin-uchebnik" "field_cover_color" => Illuminate\Database\Eloquent\Collection {#1163 #items: array:2 [ 0 => App\Models\Term {#1164 #connection: "mysql" #table: "terms" #primaryKey: "id" #keyType: "int" +incrementing: false #with: [] #withCount: [] +preventsLazyLoading: false #perPage: 15 +exists: true +wasRecentlyCreated: false #escapeWhenCastingToString: false #attributes: array:6 [ …6] #original: array:6 [ …6] #changes: [] #casts: [] #classCastCache: [] #attributeCastCache: [] #dateFormat: null #appends: [] #dispatchesEvents: [] #observables: [] #relations: [] #touches: [] +timestamps: true +usesUniqueIds: false #hidden: [] #visible: [] #fillable: [] #guarded: array:1 [ …1] } 1 => App\Models\Term {#1165 #connection: "mysql" #table: "terms" #primaryKey: "id" #keyType: "int" +incrementing: false #with: [] #withCount: [] +preventsLazyLoading: false #perPage: 15 +exists: true +wasRecentlyCreated: false #escapeWhenCastingToString: false #attributes: array:6 [ …6] #original: array:6 [ …6] #changes: [] #casts: [] #classCastCache: [] #attributeCastCache: [] #dateFormat: null #appends: [] #dispatchesEvents: [] #observables: [] #relations: [] #touches: [] +timestamps: true +usesUniqueIds: false #hidden: [] #visible: [] #fillable: [] #guarded: array:1 [ …1] } ] #escapeWhenCastingToString: false } "field_metatags_title" => null "field_metatags_description" => null "field_h1" => null "field_description_top" => null "field_description_bottom" => null "breadcrumbs" => array:3 [ "class" => 381 "subject" => 558 "class_subject" => 500 ] ] #original: array:50 [ "id" => 1003 "created_at" => "2026-04-10 13:58:26" "updated_at" => null "field_tree_default_status" => "tasks" "field_pages_status" => null "field_subject" => Illuminate\Database\Eloquent\Collection {#1133} "field_class" => Illuminate\Database\Eloquent\Collection {#1134} "field_publisher" => Illuminate\Database\Eloquent\Collection {#1136} "field_author" => Illuminate\Database\Eloquent\Collection {#1138} "field_author_foreign" => Illuminate\Database\Eloquent\Collection {#1144} "field_book_type" => Illuminate\Database\Eloquent\Collection {#1145} "field_country" => Illuminate\Database\Eloquent\Collection {#1147} "field_city" => Illuminate\Database\Eloquent\Collection {#1149} "field_series" => Illuminate\Database\Eloquent\Collection {#1151} "field_umk" => Illuminate\Database\Eloquent\Collection {#1152} "field_level_of_education" => Illuminate\Database\Eloquent\Collection {#1153} "field_standart_of_education" => Illuminate\Database\Eloquent\Collection {#1155} "field_publication_number" => "10" "field_publication_type" => Illuminate\Database\Eloquent\Collection {#1157} "field_under_the_edition" => Illuminate\Database\Eloquent\Collection {#1159} "field_under_the_edition_degree" => "доктор химических наук, академика РАН" "field_cover_description" => "с радугой" "field_publication_year" => "2023" "field_publication_year_until" => null "field_part" => "" "field_part_writing" => "" "field_second_foreign_language" => null "field_for_whom" => null "field_allowed" => "Допущено Министерством просвещения Российской Федерации" "field_reserve_field" => null "field_link_to_source" => null "field_tasks_count" => "697" "field_priority" => "10" "field_default_folder" => "/himiya_10/eremin-u23/" "field_isbn" => null "field_cover" => array:1 [ 0 => "/media/himiya_10/eremin-u23/covers/cover1.webp?ts=1738768732" ] "field_cover_alts" => array:1 [ 0 => "" ] "field_covers" => array:1 [ 0 => array:4 [ "path" => "/media/himiya_10/eremin-u23/covers/cover1.webp?ts=1738768732" "alt" => "" "width" => "1200" "height" => "1576" ] ] "field_popular_book" => null "field_recommended_books" => Illuminate\Database\Eloquent\Collection {#1160} "field_new_book" => Illuminate\Database\Eloquent\Collection {#1161} "field_old_book" => Illuminate\Database\Eloquent\Collection {#1162} "field_url" => "/10-klass/himiya/eremin-uchebnik" "field_cover_color" => Illuminate\Database\Eloquent\Collection {#1163} "field_metatags_title" => null "field_metatags_description" => null "field_h1" => null "field_description_top" => null "field_description_bottom" => null "breadcrumbs" => array:3 [ "class" => 381 "subject" => 558 "class_subject" => 500 ] ] #changes: [] #casts: [] #classCastCache: [] #attributeCastCache: [] #dateFormat: null #appends: [] #dispatchesEvents: [] #observables: [] #relations: [] #touches: [] +timestamps: true +usesUniqueIds: false #hidden: [] #visible: [] #fillable: [] #guarded: array:1 [ 0 => "*" ] } ] #escapeWhenCastingToString: false } "branch_parent" => Illuminate\Database\Eloquent\Collection {#1166 #items: [] #escapeWhenCastingToString: false } ] #original: array:24 [ "id" => 662723 "created_at" => "2026-04-10 13:58:26" "updated_at" => null "field_display_title" => "Углеводороды" "field_branch_order" => "3" "field_url" => null "field_branch_type" => Illuminate\Database\Eloquent\Collection {#1132} "field_page_start" => "139" "field_branch_display" => "0" "field_branch_expanded" => "0" "field_display_branch_in_title" => "1" "field_display_task_interval" => "0" "field_display_branch_page" => "1" "field_branch_title_in_content" => "0" "field_navigation_title" => null "field_metatags_title" => null "field_metatags_description" => null "field_h1" => null "field_description_top" => null "field_description_bottom" => null "field_branch_cover" => [] "field_branch_covers" => [] "book" => Illuminate\Database\Eloquent\Collection {#1168} "branch_parent" => Illuminate\Database\Eloquent\Collection {#1166} ] #changes: [] #casts: [] #classCastCache: [] #attributeCastCache: [] #dateFormat: null #appends: [] #dispatchesEvents: [] #observables: [] #relations: [] #touches: [] +timestamps: true +usesUniqueIds: false #hidden: [] #visible: [] #fillable: [] #guarded: array:1 [ 0 => "*" ] } 1 => App\Models\Branch {#1167 #connection: "mysql" #table: "branches" #primaryKey: "id" #keyType: "int" +incrementing: true #with: [] #withCount: [] +preventsLazyLoading: false #perPage: 15 +exists: true +wasRecentlyCreated: false #escapeWhenCastingToString: false #attributes: array:24 [ "id" => 662742 "created_at" => "2026-04-10 13:58:26" "updated_at" => null "field_display_title" => "Галогенопроизводные углеводородов" "field_branch_order" => "42" "field_url" => null "field_branch_type" => Illuminate\Database\Eloquent\Collection {#1172 #items: array:1 [ 0 => App\Models\Term {#1169 #connection: "mysql" #table: "terms" #primaryKey: "id" #keyType: "int" +incrementing: false #with: [] #withCount: [] +preventsLazyLoading: false #perPage: 15 +exists: true +wasRecentlyCreated: false #escapeWhenCastingToString: false #attributes: array:7 [ "id" => 32 "created_at" => "2026-04-10 13:58:26" "updated_at" => null "name" => "Параграф" "field_cases" => array:6 [ …6] "field_page_check_not_needed" => null "field_short_name" => "§" ] #original: array:7 [ "id" => 32 "created_at" => "2026-04-10 13:58:26" "updated_at" => null "name" => "Параграф" "field_cases" => array:6 [ …6] "field_page_check_not_needed" => null "field_short_name" => "§" ] #changes: [] #casts: [] #classCastCache: [] #attributeCastCache: [] #dateFormat: null #appends: [] #dispatchesEvents: [] #observables: [] #relations: [] #touches: [] +timestamps: true +usesUniqueIds: false #hidden: [] #visible: [] #fillable: [] #guarded: array:1 [ 0 => "*" ] } ] #escapeWhenCastingToString: false } "field_page_start" => "219" "field_branch_display" => "0" "field_branch_expanded" => "0" "field_display_branch_in_title" => "1" "field_display_task_interval" => "0" "field_display_branch_page" => "1" "field_branch_title_in_content" => "0" "field_navigation_title" => null "field_metatags_title" => null "field_metatags_description" => null "field_h1" => null "field_description_top" => null "field_description_bottom" => null "field_branch_cover" => [] "field_branch_covers" => [] "book" => Illuminate\Database\Eloquent\Collection {#1171 #items: array:1 [ 0 => App\Models\Book {#1131} ] #escapeWhenCastingToString: false } "branch_parent" => Illuminate\Database\Eloquent\Collection {#1170 #items: array:1 [ 0 => App\Models\Branch {#1034} ] #escapeWhenCastingToString: false } ] #original: array:24 [ "id" => 662742 "created_at" => "2026-04-10 13:58:26" "updated_at" => null "field_display_title" => "Галогенопроизводные углеводородов" "field_branch_order" => "42" "field_url" => null "field_branch_type" => Illuminate\Database\Eloquent\Collection {#1172} "field_page_start" => "219" "field_branch_display" => "0" "field_branch_expanded" => "0" "field_display_branch_in_title" => "1" "field_display_task_interval" => "0" "field_display_branch_page" => "1" "field_branch_title_in_content" => "0" "field_navigation_title" => null "field_metatags_title" => null "field_metatags_description" => null "field_h1" => null "field_description_top" => null "field_description_bottom" => null "field_branch_cover" => [] "field_branch_covers" => [] "book" => Illuminate\Database\Eloquent\Collection {#1171} "branch_parent" => Illuminate\Database\Eloquent\Collection {#1170} ] #changes: [] #casts: [] #classCastCache: [] #attributeCastCache: [] #dateFormat: null #appends: [] #dispatchesEvents: [] #observables: [] #relations: [] #touches: [] +timestamps: true +usesUniqueIds: false #hidden: [] #visible: [] #fillable: [] #guarded: array:1 [ 0 => "*" ] } ] #escapeWhenCastingToString: false } "content" => Illuminate\Database\Eloquent\Collection {#1117 #items: array:3 [ 0 => App\Models\Element {#1110 #connection: "mysql" #table: "elements" #primaryKey: "id" #keyType: "int" +incrementing: true #with: [] #withCount: [] +preventsLazyLoading: false #perPage: 15 +exists: true +wasRecentlyCreated: false #escapeWhenCastingToString: false #attributes: array:7 [ "id" => 818900 "created_at" => "2026-04-10 13:58:26" "updated_at" => null "edition" => Illuminate\Database\Eloquent\Collection {#1102 #items: array:1 [ 0 => App\Models\Edition {#1094 #connection: "mysql" #table: "editions" #primaryKey: "id" #keyType: "int" +incrementing: false #with: [] #withCount: [] +preventsLazyLoading: false #perPage: 15 +exists: true +wasRecentlyCreated: false #escapeWhenCastingToString: false #attributes: array:21 [ "id" => 1829 "created_at" => "2026-04-10 13:58:26" "updated_at" => null "title" => "Условие" "field_order" => "1" "field_publisher" => Illuminate\Database\Eloquent\Collection {#1109 …2} "field_content_type" => "free" "field_content_mode" => "text, image" "field_page_content_mode" => "image" "field_content_text_checked" => null "field_page_content_text_checked" => "0" "field_solution_author" => "Автор" "field_moderator" => "vadim" "field_edition_type" => "statement" "field_root_dir" => "0-" "field_responsible" => Illuminate\Database\Eloquent\Collection {#1106 …2} "field_comment" => null "field_similar_book" => Illuminate\Database\Eloquent\Collection {#1107 …2} "field_process_formula" => "katex" "field_edition_group" => Illuminate\Database\Eloquent\Collection {#1104 …2} "field_content_source" => null ] #original: array:21 [ "id" => 1829 "created_at" => "2026-04-10 13:58:26" "updated_at" => null "title" => "Условие" "field_order" => "1" "field_publisher" => Illuminate\Database\Eloquent\Collection {#1109 …2} "field_content_type" => "free" "field_content_mode" => "text, image" "field_page_content_mode" => "image" "field_content_text_checked" => null "field_page_content_text_checked" => "0" "field_solution_author" => "Автор" "field_moderator" => "vadim" "field_edition_type" => "statement" "field_root_dir" => "0-" "field_responsible" => Illuminate\Database\Eloquent\Collection {#1106 …2} "field_comment" => null "field_similar_book" => Illuminate\Database\Eloquent\Collection {#1107 …2} "field_process_formula" => "katex" "field_edition_group" => Illuminate\Database\Eloquent\Collection {#1104 …2} "field_content_source" => null ] #changes: [] #casts: [] #classCastCache: [] #attributeCastCache: [] #dateFormat: null #appends: [] #dispatchesEvents: [] #observables: [] #relations: [] #touches: [] +timestamps: true +usesUniqueIds: false #hidden: [] #visible: [] #fillable: [] #guarded: array:1 [ 0 => "*" ] } ] #escapeWhenCastingToString: false } "task" => array:2 [ "refs" => "663193" "type" => "task" ] "text" => "<p><strong>4.</strong> Расположите галогенопроизводные углеводородов в ряд в порядке увеличения реакционной способности в реакциях нуклеофильного замещения. Мотивируйте свой ответ. Галогенопроизводные: бромэтан, хлорэтан, хлорэтен, 3-бромбутен-1.</p>" "img" => array:1 [ 0 => array:5 [ "name" => "4-1.jpg" "alt" => null "width" => "849" "height" => 165 "path" => "/media/himiya_10/eremin-u23/0-42/4-1.webp?ts=1738779615" ] ] ] #original: array:7 [ "id" => 818900 "created_at" => "2026-04-10 13:58:26" "updated_at" => null "edition" => Illuminate\Database\Eloquent\Collection {#1102} "task" => array:2 [ "refs" => "663193" "type" => "task" ] "text" => "<p><strong>4.</strong> Расположите галогенопроизводные углеводородов в ряд в порядке увеличения реакционной способности в реакциях нуклеофильного замещения. Мотивируйте свой ответ. Галогенопроизводные: бромэтан, хлорэтан, хлорэтен, 3-бромбутен-1.</p>" "img" => array:1 [ 0 => array:5 [ "name" => "4-1.jpg" "alt" => null "width" => "849" "height" => 165 "path" => "/media/himiya_10/eremin-u23/0-42/4-1.webp?ts=1738779615" ] ] ] #changes: [] #casts: [] #classCastCache: [] #attributeCastCache: [] #dateFormat: null #appends: [] #dispatchesEvents: [] #observables: [] #relations: [] #touches: [] +timestamps: true +usesUniqueIds: false #hidden: [] #visible: [] #fillable: [] #guarded: array:1 [ 0 => "*" ] } 1 => App\Models\Element {#1105 #connection: "mysql" #table: "elements" #primaryKey: "id" #keyType: "int" +incrementing: true #with: [] #withCount: [] +preventsLazyLoading: false #perPage: 15 +exists: true +wasRecentlyCreated: false #escapeWhenCastingToString: false #attributes: array:6 [ "id" => 819141 "created_at" => "2026-04-10 13:58:26" "updated_at" => null "edition" => Illuminate\Database\Eloquent\Collection {#1089 #items: array:1 [ 0 => App\Models\Edition {#1103 #connection: "mysql" #table: "editions" #primaryKey: "id" #keyType: "int" +incrementing: false #with: [] #withCount: [] +preventsLazyLoading: false #perPage: 15 +exists: true +wasRecentlyCreated: false #escapeWhenCastingToString: false #attributes: array:21 [ "id" => 1830 "created_at" => "2026-04-10 13:58:26" "updated_at" => null "title" => "Решение" "field_order" => "2" "field_publisher" => Illuminate\Database\Eloquent\Collection {#1101 …2} "field_content_type" => "free" "field_content_mode" => "image" "field_page_content_mode" => "" "field_content_text_checked" => "0" "field_page_content_text_checked" => "0" "field_solution_author" => "Ладыко (Торчило)" "field_moderator" => "vadim" "field_edition_type" => "solution" "field_root_dir" => "1-" "field_responsible" => Illuminate\Database\Eloquent\Collection {#1098 …2} "field_comment" => null "field_similar_book" => Illuminate\Database\Eloquent\Collection {#1099 …2} "field_process_formula" => "" "field_edition_group" => Illuminate\Database\Eloquent\Collection {#1096 …2} "field_content_source" => null ] #original: array:21 [ "id" => 1830 "created_at" => "2026-04-10 13:58:26" "updated_at" => null "title" => "Решение" "field_order" => "2" "field_publisher" => Illuminate\Database\Eloquent\Collection {#1101 …2} "field_content_type" => "free" "field_content_mode" => "image" "field_page_content_mode" => "" "field_content_text_checked" => "0" "field_page_content_text_checked" => "0" "field_solution_author" => "Ладыко (Торчило)" "field_moderator" => "vadim" "field_edition_type" => "solution" "field_root_dir" => "1-" "field_responsible" => Illuminate\Database\Eloquent\Collection {#1098 …2} "field_comment" => null "field_similar_book" => Illuminate\Database\Eloquent\Collection {#1099 …2} "field_process_formula" => "" "field_edition_group" => Illuminate\Database\Eloquent\Collection {#1096 …2} "field_content_source" => null ] #changes: [] #casts: [] #classCastCache: [] #attributeCastCache: [] #dateFormat: null #appends: [] #dispatchesEvents: [] #observables: [] #relations: [] #touches: [] +timestamps: true +usesUniqueIds: false #hidden: [] #visible: [] #fillable: [] #guarded: array:1 [ 0 => "*" ] } ] #escapeWhenCastingToString: false } "task" => array:2 [ "refs" => "663193" "type" => "task" ] "img" => array:1 [ 0 => array:5 [ "name" => "4-1.jpg" "alt" => null "width" => "1819" "height" => 205 "path" => "/media/himiya_10/eremin-u23/1-42/4-1.webp?ts=1738779689" ] ] ] #original: array:6 [ "id" => 819141 "created_at" => "2026-04-10 13:58:26" "updated_at" => null "edition" => Illuminate\Database\Eloquent\Collection {#1089} "task" => array:2 [ "refs" => "663193" "type" => "task" ] "img" => array:1 [ 0 => array:5 [ "name" => "4-1.jpg" "alt" => null "width" => "1819" "height" => 205 "path" => "/media/himiya_10/eremin-u23/1-42/4-1.webp?ts=1738779689" ] ] ] #changes: [] #casts: [] #classCastCache: [] #attributeCastCache: [] #dateFormat: null #appends: [] #dispatchesEvents: [] #observables: [] #relations: [] #touches: [] +timestamps: true +usesUniqueIds: false #hidden: [] #visible: [] #fillable: [] #guarded: array:1 [ 0 => "*" ] } 2 => App\Models\Element {#1097 #connection: "mysql" #table: "elements" #primaryKey: "id" #keyType: "int" +incrementing: true #with: [] #withCount: [] +preventsLazyLoading: false #perPage: 15 +exists: true +wasRecentlyCreated: false #escapeWhenCastingToString: false #attributes: array:6 [ "id" => 1515597 "created_at" => "2026-04-10 13:58:26" "updated_at" => null "edition" => Illuminate\Database\Eloquent\Collection {#1086 #items: array:1 [ 0 => App\Models\Edition {#1095 #connection: "mysql" #table: "editions" #primaryKey: "id" #keyType: "int" +incrementing: false #with: [] #withCount: [] +preventsLazyLoading: false #perPage: 15 +exists: true +wasRecentlyCreated: false #escapeWhenCastingToString: false #attributes: array:21 [ "id" => 5553 "created_at" => "2026-04-10 13:58:26" "updated_at" => null "title" => "Решение 2" "field_order" => "3" "field_publisher" => Illuminate\Database\Eloquent\Collection {#1092 …2} "field_content_type" => "free" "field_content_mode" => "text" "field_page_content_mode" => "" "field_content_text_checked" => null "field_page_content_text_checked" => "0" "field_solution_author" => "Gemini 2.5 Pro" "field_moderator" => "tolik" "field_edition_type" => "solution" "field_root_dir" => "2-" "field_responsible" => Illuminate\Database\Eloquent\Collection {#1091 …2} "field_comment" => null "field_similar_book" => Illuminate\Database\Eloquent\Collection {#1090 …2} "field_process_formula" => "katex" "field_edition_group" => Illuminate\Database\Eloquent\Collection {#1087 …2} "field_content_source" => null ] #original: array:21 [ "id" => 5553 "created_at" => "2026-04-10 13:58:26" "updated_at" => null "title" => "Решение 2" "field_order" => "3" "field_publisher" => Illuminate\Database\Eloquent\Collection {#1092 …2} "field_content_type" => "free" "field_content_mode" => "text" "field_page_content_mode" => "" "field_content_text_checked" => null "field_page_content_text_checked" => "0" "field_solution_author" => "Gemini 2.5 Pro" "field_moderator" => "tolik" "field_edition_type" => "solution" "field_root_dir" => "2-" "field_responsible" => Illuminate\Database\Eloquent\Collection {#1091 …2} "field_comment" => null "field_similar_book" => Illuminate\Database\Eloquent\Collection {#1090 …2} "field_process_formula" => "katex" "field_edition_group" => Illuminate\Database\Eloquent\Collection {#1087 …2} "field_content_source" => null ] #changes: [] #casts: [] #classCastCache: [] #attributeCastCache: [] #dateFormat: null #appends: [] #dispatchesEvents: [] #observables: [] #relations: [] #touches: [] +timestamps: true +usesUniqueIds: false #hidden: [] #visible: [] #fillable: [] #guarded: array:1 [ 0 => "*" ] } ] #escapeWhenCastingToString: false } "task" => array:2 [ "refs" => "663193" "type" => "task" ] "text" => "<p>Реакционная способность галогенопроизводных в реакциях нуклеофильного замещения ($S_N$) зависит от нескольких ключевых факторов:</p><ul><li> Прочность связи углерод-галоген (C-Hal) и способность галогена выступать в качестве уходящей группы. </li><li> Гибридизация атома углерода, связанного с галогеном. </li><li> Возможность стабилизации промежуточного карбкатиона (для механизма $S_N1$) или переходного состояния (для механизма $S_N2$). </li></ul><p>Рассмотрим каждое из предложенных соединений:</p><p><strong>Хлорэтен (винилхлорид)</strong><br>Структурная формула: $CH_2=CH-Cl$.<br>В этой молекуле атом хлора связан с атомом углерода, находящимся в состоянии $sp^2$-гибридизации (углерод при двойной связи). Связь $C_{sp^2}-Cl$ короче и прочнее, чем связь $C_{sp^3}-Cl$ в алкилгалогенидах. Кроме того, неподеленная пара электронов атома хлора вступает в p,π-сопряжение с π-системой двойной связи. Это придает связи C-Cl характер частично двойной связи, что еще больше затрудняет ее разрыв. По этим причинам винилгалогениды, как правило, очень инертны в реакциях нуклеофильного замещения. Хлорэтен будет наименее реакционноспособным в данном ряду.</p><p><strong>Хлорэтан</strong><br>Структурная формула: $CH_3-CH_2-Cl$.<br>Это первичный алкилгалогенид. Атом хлора связан с $sp^3$-гибридизованным атомом углерода. Он вступает в реакции $S_N$ значительно легче, чем хлорэтен. Реакционная способность определяется прочностью связи C-Cl и стабильностью уходящей группы $Cl^-$.</p><p><strong>Бромэтан</strong><br>Структурная формула: $CH_3-CH_2-Br$.<br>Это также первичный алкилгалогенид, структурно аналогичный хлорэтану. Однако связь C-Br длиннее и слабее связи C-Cl, а бромид-ион ($Br^−$) является лучшей уходящей группой, чем хлорид-ион ($Cl^−$), так как он является анионом более сильной кислоты HBr. Следовательно, бромэтан более реакционноспособен в реакциях нуклеофильного замещения, чем хлорэтан.</p><p><strong>3-бромбутен-1</strong><br>Структурная формула: $CH_2=CH-CH(Br)-CH_3$.<br>Это аллильный галогенид. Атом брома связан с $sp^3$-гибридизованным атомом углерода, который находится в α-положении к двойной связи. Аллилгалогениды обладают аномально высокой реакционной способностью в реакциях $S_N$. Это связано с тем, что при гетеролитическом разрыве связи C-Br образуется аллильный карбкатион, который стабилизирован за счет резонанса (делокализации положительного заряда по π-системе):<br>$CH_2=CH-\stackrel{+}{C}H-CH_3 \leftrightarrow \stackrel{+}{C}H_2-CH=CH-CH_3$<br>Такая стабилизация значительно понижает энергию активации процесса, делая 3-бромбутен-1 наиболее активным соединением в данном ряду.</p><p>Таким образом, располагая соединения в порядке увеличения их реакционной способности в реакциях нуклеофильного замещения, получаем следующий ряд:<br>Хлорэтен < Хлорэтан < Бромэтан < 3-бромбутен-1<br><strong>Ответ:</strong> Ряд по увеличению реакционной способности: хлорэтен < хлорэтан < бромэтан < 3-бромбутен-1.</p>" ] #original: array:6 [ "id" => 1515597 "created_at" => "2026-04-10 13:58:26" "updated_at" => null "edition" => Illuminate\Database\Eloquent\Collection {#1086} "task" => array:2 [ "refs" => "663193" "type" => "task" ] "text" => "<p>Реакционная способность галогенопроизводных в реакциях нуклеофильного замещения ($S_N$) зависит от нескольких ключевых факторов:</p><ul><li> Прочность связи углерод-галоген (C-Hal) и способность галогена выступать в качестве уходящей группы. </li><li> Гибридизация атома углерода, связанного с галогеном. </li><li> Возможность стабилизации промежуточного карбкатиона (для механизма $S_N1$) или переходного состояния (для механизма $S_N2$). </li></ul><p>Рассмотрим каждое из предложенных соединений:</p><p><strong>Хлорэтен (винилхлорид)</strong><br>Структурная формула: $CH_2=CH-Cl$.<br>В этой молекуле атом хлора связан с атомом углерода, находящимся в состоянии $sp^2$-гибридизации (углерод при двойной связи). Связь $C_{sp^2}-Cl$ короче и прочнее, чем связь $C_{sp^3}-Cl$ в алкилгалогенидах. Кроме того, неподеленная пара электронов атома хлора вступает в p,π-сопряжение с π-системой двойной связи. Это придает связи C-Cl характер частично двойной связи, что еще больше затрудняет ее разрыв. По этим причинам винилгалогениды, как правило, очень инертны в реакциях нуклеофильного замещения. Хлорэтен будет наименее реакционноспособным в данном ряду.</p><p><strong>Хлорэтан</strong><br>Структурная формула: $CH_3-CH_2-Cl$.<br>Это первичный алкилгалогенид. Атом хлора связан с $sp^3$-гибридизованным атомом углерода. Он вступает в реакции $S_N$ значительно легче, чем хлорэтен. Реакционная способность определяется прочностью связи C-Cl и стабильностью уходящей группы $Cl^-$.</p><p><strong>Бромэтан</strong><br>Структурная формула: $CH_3-CH_2-Br$.<br>Это также первичный алкилгалогенид, структурно аналогичный хлорэтану. Однако связь C-Br длиннее и слабее связи C-Cl, а бромид-ион ($Br^−$) является лучшей уходящей группой, чем хлорид-ион ($Cl^−$), так как он является анионом более сильной кислоты HBr. Следовательно, бромэтан более реакционноспособен в реакциях нуклеофильного замещения, чем хлорэтан.</p><p><strong>3-бромбутен-1</strong><br>Структурная формула: $CH_2=CH-CH(Br)-CH_3$.<br>Это аллильный галогенид. Атом брома связан с $sp^3$-гибридизованным атомом углерода, который находится в α-положении к двойной связи. Аллилгалогениды обладают аномально высокой реакционной способностью в реакциях $S_N$. Это связано с тем, что при гетеролитическом разрыве связи C-Br образуется аллильный карбкатион, который стабилизирован за счет резонанса (делокализации положительного заряда по π-системе):<br>$CH_2=CH-\stackrel{+}{C}H-CH_3 \leftrightarrow \stackrel{+}{C}H_2-CH=CH-CH_3$<br>Такая стабилизация значительно понижает энергию активации процесса, делая 3-бромбутен-1 наиболее активным соединением в данном ряду.</p><p>Таким образом, располагая соединения в порядке увеличения их реакционной способности в реакциях нуклеофильного замещения, получаем следующий ряд:<br>Хлорэтен < Хлорэтан < Бромэтан < 3-бромбутен-1<br><strong>Ответ:</strong> Ряд по увеличению реакционной способности: хлорэтен < хлорэтан < бромэтан < 3-бромбутен-1.</p>" ] #changes: [] #casts: [] #classCastCache: [] #attributeCastCache: [] #dateFormat: null #appends: [] #dispatchesEvents: [] #observables: [] #relations: [] #touches: [] +timestamps: true +usesUniqueIds: false #hidden: [] #visible: [] #fillable: [] #guarded: array:1 [ 0 => "*" ] } ] #escapeWhenCastingToString: false } "next" => array:2 [ "refs" => "663194" "type" => "task" ] "previous" => array:2 [ "refs" => "663192" "type" => "task" ] "book" => Illuminate\Database\Eloquent\Collection {#1113 #items: array:1 [ 0 => App\Models\Book {#1131} ] #escapeWhenCastingToString: false } "page" => Illuminate\Database\Eloquent\Collection {#1116 #items: array:1 [ 0 => App\Models\BookPage {#1081 #connection: "mysql" #table: "book_pages" #primaryKey: "id" #keyType: "int" +incrementing: true #with: [] #withCount: [] +preventsLazyLoading: false #perPage: 15 +exists: true +wasRecentlyCreated: false #escapeWhenCastingToString: false #attributes: array:21 [ "id" => 926122 "created_at" => "2026-04-10 13:58:26" "updated_at" => null "field_page_start" => "226" "field_url" => "/10-klass/himiya/eremin-uchebnik/page-226" "field_display_title" => "226" "field_folder" => "1" "field_image_name" => "226" "field_branch_parent" => Illuminate\Database\Eloquent\Collection {#1082 #items: [] #escapeWhenCastingToString: false } "field_weight" => "0" "field_book_parent" => Illuminate\Database\Eloquent\Collection {#1088 #items: array:1 [ 0 => App\Models\Book {#1131} ] #escapeWhenCastingToString: false } "field_metatags_title" => null "field_metatags_description" => null "field_h1" => null "field_description_top" => null "field_description_bottom" => null "edition_groups" => Illuminate\Database\Eloquent\Collection {#1085 #items: [] #escapeWhenCastingToString: false } "content" => Illuminate\Database\Eloquent\Collection {#1124 #items: array:1 [ 0 => App\Models\Element {#1121 #connection: "mysql" #table: "elements" #primaryKey: "id" #keyType: "int" +incrementing: true #with: [] #withCount: [] +preventsLazyLoading: false #perPage: 15 +exists: true +wasRecentlyCreated: false #escapeWhenCastingToString: false #attributes: array:6 [ …6] #original: array:6 [ …6] #changes: [] #casts: [] #classCastCache: [] #attributeCastCache: [] #dateFormat: null #appends: [] #dispatchesEvents: [] #observables: [] #relations: [] #touches: [] +timestamps: true +usesUniqueIds: false #hidden: [] #visible: [] #fillable: [] #guarded: array:1 [ …1] } ] #escapeWhenCastingToString: false } "next" => array:2 [ "refs" => "926123" "type" => "book_page" ] "previous" => array:2 [ "refs" => "926121" "type" => "book_page" ] "tasks" => Illuminate\Database\Eloquent\Collection {#1284 #items: array:13 [ 0 => App\Models\Task {#1304 #connection: "mysql" #table: "tasks" #primaryKey: "id" #keyType: "int" +incrementing: true #with: [] #withCount: [] +preventsLazyLoading: false #perPage: 15 +exists: true +wasRecentlyCreated: false #escapeWhenCastingToString: false #attributes: array:24 [ …24] #original: array:24 [ …24] #changes: [] #casts: [] #classCastCache: [] #attributeCastCache: [] #dateFormat: null #appends: [] #dispatchesEvents: [] #observables: [] #relations: [] #touches: [] +timestamps: true +usesUniqueIds: false #hidden: [] #visible: [] #fillable: [] #guarded: array:1 [ …1] } 1 => App\Models\Task {#1311 #connection: "mysql" #table: "tasks" #primaryKey: "id" #keyType: "int" +incrementing: true #with: [] #withCount: [] +preventsLazyLoading: false #perPage: 15 +exists: true +wasRecentlyCreated: false #escapeWhenCastingToString: false #attributes: array:24 [ …24] #original: array:24 [ …24] #changes: [] #casts: [] #classCastCache: [] #attributeCastCache: [] #dateFormat: null #appends: [] #dispatchesEvents: [] #observables: [] #relations: [] #touches: [] +timestamps: true +usesUniqueIds: false #hidden: [] #visible: [] #fillable: [] #guarded: array:1 [ …1] } 2 => App\Models\Task {#1317 #connection: "mysql" #table: "tasks" #primaryKey: "id" #keyType: "int" +incrementing: true #with: [] #withCount: [] +preventsLazyLoading: false #perPage: 15 +exists: true +wasRecentlyCreated: false #escapeWhenCastingToString: false #attributes: array:24 [ …24] #original: array:24 [ …24] #changes: [] #casts: [] #classCastCache: [] #attributeCastCache: [] #dateFormat: null #appends: [] #dispatchesEvents: [] #observables: [] #relations: [] #touches: [] +timestamps: true +usesUniqueIds: false #hidden: [] #visible: [] #fillable: [] #guarded: array:1 [ …1] } 3 => App\Models\Task {#1322 #connection: "mysql" #table: "tasks" #primaryKey: "id" #keyType: "int" +incrementing: true #with: [] #withCount: [] +preventsLazyLoading: false #perPage: 15 +exists: true +wasRecentlyCreated: false #escapeWhenCastingToString: false #attributes: array:24 [ …24] #original: array:24 [ …24] #changes: [] #casts: [] #classCastCache: [] #attributeCastCache: [] #dateFormat: null #appends: [] #dispatchesEvents: [] #observables: [] #relations: [] #touches: [] +timestamps: true +usesUniqueIds: false #hidden: [] #visible: [] #fillable: [] #guarded: array:1 [ …1] } 4 => App\Models\Task {#1336 #connection: "mysql" #table: "tasks" #primaryKey: "id" #keyType: "int" +incrementing: true #with: [] #withCount: [] +preventsLazyLoading: false #perPage: 15 +exists: true +wasRecentlyCreated: false #escapeWhenCastingToString: false #attributes: array:24 [ …24] #original: array:24 [ …24] #changes: [] #casts: [] #classCastCache: [] #attributeCastCache: [] #dateFormat: null #appends: [] #dispatchesEvents: [] #observables: [] #relations: [] #touches: [] +timestamps: true +usesUniqueIds: false #hidden: [] #visible: [] #fillable: [] #guarded: array:1 [ …1] } 5 => App\Models\Task {#1350 #connection: "mysql" #table: "tasks" #primaryKey: "id" #keyType: "int" +incrementing: true #with: [] #withCount: [] +preventsLazyLoading: false #perPage: 15 +exists: true +wasRecentlyCreated: false #escapeWhenCastingToString: false #attributes: array:24 [ …24] #original: array:24 [ …24] #changes: [] #casts: [] #classCastCache: [] #attributeCastCache: [] #dateFormat: null #appends: [] #dispatchesEvents: [] #observables: [] #relations: [] #touches: [] +timestamps: true +usesUniqueIds: false #hidden: [] #visible: [] #fillable: [] #guarded: array:1 [ …1] } 6 => App\Models\Task {#1364 #connection: "mysql" #table: "tasks" #primaryKey: "id" #keyType: "int" +incrementing: true #with: [] #withCount: [] +preventsLazyLoading: false #perPage: 15 +exists: true +wasRecentlyCreated: false #escapeWhenCastingToString: false #attributes: array:24 [ …24] #original: array:24 [ …24] #changes: [] #casts: [] #classCastCache: [] #attributeCastCache: [] #dateFormat: null #appends: [] #dispatchesEvents: [] #observables: [] #relations: [] #touches: [] +timestamps: true +usesUniqueIds: false #hidden: [] #visible: [] #fillable: [] #guarded: array:1 [ …1] } 7 => App\Models\Task {#1378 #connection: "mysql" #table: "tasks" #primaryKey: "id" #keyType: "int" +incrementing: true #with: [] #withCount: [] +preventsLazyLoading: false #perPage: 15 +exists: true +wasRecentlyCreated: false #escapeWhenCastingToString: false #attributes: array:24 [ …24] #original: array:24 [ …24] #changes: [] #casts: [] #classCastCache: [] #attributeCastCache: [] #dateFormat: null #appends: [] #dispatchesEvents: [] #observables: [] #relations: [] #touches: [] +timestamps: true +usesUniqueIds: false #hidden: [] #visible: [] #fillable: [] #guarded: array:1 [ …1] } 8 => App\Models\Task {#1392 #connection: "mysql" #table: "tasks" #primaryKey: "id" #keyType: "int" +incrementing: true #with: [] #withCount: [] +preventsLazyLoading: false #perPage: 15 +exists: true +wasRecentlyCreated: false #escapeWhenCastingToString: false #attributes: array:24 [ …24] #original: array:24 [ …24] #changes: [] #casts: [] #classCastCache: [] #attributeCastCache: [] #dateFormat: null #appends: [] #dispatchesEvents: [] #observables: [] #relations: [] #touches: [] +timestamps: true +usesUniqueIds: false #hidden: [] #visible: [] #fillable: [] #guarded: array:1 [ …1] } 9 => App\Models\Task {#1406 #connection: "mysql" #table: "tasks" #primaryKey: "id" #keyType: "int" +incrementing: true #with: [] #withCount: [] +preventsLazyLoading: false #perPage: 15 +exists: true +wasRecentlyCreated: false #escapeWhenCastingToString: false #attributes: array:24 [ …24] #original: array:24 [ …24] #changes: [] #casts: [] #classCastCache: [] #attributeCastCache: [] #dateFormat: null #appends: [] #dispatchesEvents: [] #observables: [] #relations: [] #touches: [] +timestamps: true +usesUniqueIds: false #hidden: [] #visible: [] #fillable: [] #guarded: array:1 [ …1] } 10 => App\Models\Task {#1420 #connection: "mysql" #table: "tasks" #primaryKey: "id" #keyType: "int" +incrementing: true #with: [] #withCount: [] +preventsLazyLoading: false #perPage: 15 +exists: true +wasRecentlyCreated: false #escapeWhenCastingToString: false #attributes: array:24 [ …24] #original: array:24 [ …24] #changes: [] #casts: [] #classCastCache: [] #attributeCastCache: [] #dateFormat: null #appends: [] #dispatchesEvents: [] #observables: [] #relations: [] #touches: [] +timestamps: true +usesUniqueIds: false #hidden: [] #visible: [] #fillable: [] #guarded: array:1 [ …1] } 11 => App\Models\Task {#1434 #connection: "mysql" #table: "tasks" #primaryKey: "id" #keyType: "int" +incrementing: true #with: [] #withCount: [] +preventsLazyLoading: false #perPage: 15 +exists: true +wasRecentlyCreated: false #escapeWhenCastingToString: false #attributes: array:24 [ …24] #original: array:24 [ …24] #changes: [] #casts: [] #classCastCache: [] #attributeCastCache: [] #dateFormat: null #appends: [] #dispatchesEvents: [] #observables: [] #relations: [] #touches: [] +timestamps: true +usesUniqueIds: false #hidden: [] #visible: [] #fillable: [] #guarded: array:1 [ …1] } 12 => App\Models\Task {#1448 #connection: "mysql" #table: "tasks" #primaryKey: "id" #keyType: "int" +incrementing: true #with: [] #withCount: [] +preventsLazyLoading: false #perPage: 15 +exists: true +wasRecentlyCreated: false #escapeWhenCastingToString: false #attributes: array:24 [ …24] #original: array:24 [ …24] #changes: [] #casts: [] #classCastCache: [] #attributeCastCache: [] #dateFormat: null #appends: [] #dispatchesEvents: [] #observables: [] #relations: [] #touches: [] +timestamps: true +usesUniqueIds: false #hidden: [] #visible: [] #fillable: [] #guarded: array:1 [ …1] } ] #escapeWhenCastingToString: false } ] #original: array:21 [ "id" => 926122 "created_at" => "2026-04-10 13:58:26" "updated_at" => null "field_page_start" => "226" "field_url" => "/10-klass/himiya/eremin-uchebnik/page-226" "field_display_title" => "226" "field_folder" => "1" "field_image_name" => "226" "field_branch_parent" => Illuminate\Database\Eloquent\Collection {#1082} "field_weight" => "0" "field_book_parent" => Illuminate\Database\Eloquent\Collection {#1088} "field_metatags_title" => null "field_metatags_description" => null "field_h1" => null "field_description_top" => null "field_description_bottom" => null "edition_groups" => Illuminate\Database\Eloquent\Collection {#1085} "content" => Illuminate\Database\Eloquent\Collection {#1124} "next" => array:2 [ "refs" => "926123" "type" => "book_page" ] "previous" => array:2 [ "refs" => "926121" "type" => "book_page" ] "tasks" => Illuminate\Database\Eloquent\Collection {#1284} ] #changes: [] #casts: [] #classCastCache: [] #attributeCastCache: [] #dateFormat: null #appends: [] #dispatchesEvents: [] #observables: [] #relations: [] #touches: [] +timestamps: true +usesUniqueIds: false #hidden: [] #visible: [] #fillable: [] #guarded: array:1 [ 0 => "*" ] } ] #escapeWhenCastingToString: false } ] #original: array:24 [ "id" => 663193 "created_at" => "2026-04-10 13:58:26" "updated_at" => null "field_page_start" => "226" "field_page_end" => null "field_url" => "/10-klass/himiya/eremin-uchebnik/42-4" "field_display_title" => "4" "field_outside_task" => null "field_task_type" => Illuminate\Database\Eloquent\Collection {#1037} "field_metatags_title" => null "field_metatags_description" => null "field_h1" => null "field_description_top" => null "field_description_bottom" => null "field_match" => null "breadcrumbs" => [] "edition_groups" => Illuminate\Database\Eloquent\Collection {#1035} "top_parent_branch" => Illuminate\Database\Eloquent\Collection {#1079} "parent_branches" => Illuminate\Database\Eloquent\Collection {#1120} "content" => Illuminate\Database\Eloquent\Collection {#1117} "next" => array:2 [ "refs" => "663194" "type" => "task" ] "previous" => array:2 [ "refs" => "663192" "type" => "task" ] "book" => Illuminate\Database\Eloquent\Collection {#1113} "page" => array:2 [ "refs" => "926122" "type" => "book_page" ] ] #changes: [] #casts: [] #classCastCache: [] #attributeCastCache: [] #dateFormat: null #appends: [] #dispatchesEvents: [] #observables: [] #relations: [] #touches: [] +timestamps: true +usesUniqueIds: false #hidden: [] #visible: [] #fillable: [] #guarded: array:1 [ 0 => "*" ] }
№4 (с. 226)
Условие. №4 (с. 226)
скриншот условия
4. Расположите галогенопроизводные углеводородов в ряд в порядке увеличения реакционной способности в реакциях нуклеофильного замещения. Мотивируйте свой ответ. Галогенопроизводные: бромэтан, хлорэтан, хлорэтен, 3-бромбутен-1.
Решение. №4 (с. 226)
Решение 2. №4 (с. 226)
Реакционная способность галогенопроизводных в реакциях нуклеофильного замещения ($S_N$) зависит от нескольких ключевых факторов:
- Прочность связи углерод-галоген (C-Hal) и способность галогена выступать в качестве уходящей группы.
- Гибридизация атома углерода, связанного с галогеном.
- Возможность стабилизации промежуточного карбкатиона (для механизма $S_N1$) или переходного состояния (для механизма $S_N2$).
Рассмотрим каждое из предложенных соединений:
Хлорэтен (винилхлорид)
Структурная формула: $CH_2=CH-Cl$.
В этой молекуле атом хлора связан с атомом углерода, находящимся в состоянии $sp^2$-гибридизации (углерод при двойной связи). Связь $C_{sp^2}-Cl$ короче и прочнее, чем связь $C_{sp^3}-Cl$ в алкилгалогенидах. Кроме того, неподеленная пара электронов атома хлора вступает в p,π-сопряжение с π-системой двойной связи. Это придает связи C-Cl характер частично двойной связи, что еще больше затрудняет ее разрыв. По этим причинам винилгалогениды, как правило, очень инертны в реакциях нуклеофильного замещения. Хлорэтен будет наименее реакционноспособным в данном ряду.
Хлорэтан
Структурная формула: $CH_3-CH_2-Cl$.
Это первичный алкилгалогенид. Атом хлора связан с $sp^3$-гибридизованным атомом углерода. Он вступает в реакции $S_N$ значительно легче, чем хлорэтен. Реакционная способность определяется прочностью связи C-Cl и стабильностью уходящей группы $Cl^-$.
Бромэтан
Структурная формула: $CH_3-CH_2-Br$.
Это также первичный алкилгалогенид, структурно аналогичный хлорэтану. Однако связь C-Br длиннее и слабее связи C-Cl, а бромид-ион ($Br^−$) является лучшей уходящей группой, чем хлорид-ион ($Cl^−$), так как он является анионом более сильной кислоты HBr. Следовательно, бромэтан более реакционноспособен в реакциях нуклеофильного замещения, чем хлорэтан.
3-бромбутен-1
Структурная формула: $CH_2=CH-CH(Br)-CH_3$.
Это аллильный галогенид. Атом брома связан с $sp^3$-гибридизованным атомом углерода, который находится в α-положении к двойной связи. Аллилгалогениды обладают аномально высокой реакционной способностью в реакциях $S_N$. Это связано с тем, что при гетеролитическом разрыве связи C-Br образуется аллильный карбкатион, который стабилизирован за счет резонанса (делокализации положительного заряда по π-системе):
$CH_2=CH-\stackrel{+}{C}H-CH_3 \leftrightarrow \stackrel{+}{C}H_2-CH=CH-CH_3$
Такая стабилизация значительно понижает энергию активации процесса, делая 3-бромбутен-1 наиболее активным соединением в данном ряду.
Таким образом, располагая соединения в порядке увеличения их реакционной способности в реакциях нуклеофильного замещения, получаем следующий ряд:
Хлорэтен < Хлорэтан < Бромэтан < 3-бромбутен-1
Ответ: Ряд по увеличению реакционной способности: хлорэтен < хлорэтан < бромэтан < 3-бромбутен-1.
Другие задания:
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