Octet / Reactions

Cannizzaro Reaction

Included in Reactions.

Oxidation

Source Details

Id

cannizzaro

Name
{
  "en": "Cannizzaro Reaction",
  "ar": "Cannizzaro تفاعل",
  "cs": "Cannizzaro Reakce",
  "da": "Cannizzaro Reaktion",
  "de": "Cannizzaro Reaktion",
  "el": "Αντίδραση Cannizzaro",
  "es-419": "Reacción de Cannizzaro",
  "es-ES": "Reacción de Cannizzaro",
  "es": "Reacción de Cannizzaro",
  "fi": "Cannizzaro Reaktio",
  "fr": "Réaction de Cannizzaro",
  "he": "Cannizzaro תגובה",
  "hr": "Cannizzaro Reakcija",
  "hu": "Cannizzaro-reakció",
  "id": "Reaksi Cannizzaro",
  "it": "Reazione di Cannizzaro",
  "ja": "Cannizzaro反応",
  "ko": "Cannizzaro 반응",
  "lv": "Cannizzaro Reakcija",
  "nb": "Cannizzaro Reaksjon",
  "nl": "Cannizzaro Reactie",
  "pl": "Cannizzaro Reakcja",
  "pt-BR": "Reação de Cannizzaro",
  "pt-PT": "Reação de Cannizzaro",
  "ro": "Reacție de Cannizzaro",
  "ru": "Cannizzaro Реакция",
  "sk": "Cannizzaro Reakcia",
  "sl": "Cannizzaro Reakcija",
  "sv": "Cannizzaro Reaktion",
  "th": "ปฏิกิริยา Cannizzaro",
  "tr": "Cannizzaro reaksiyüzerindeu",
  "uk": "Cannizzaro Реакція",
  "vi": "Phản ứng Cannizzaro",
  "zh-Hans": "Cannizzaro 反应",
  "zh": "Cannizzaro 反应"
}
Type
{
  "en": "Oxidation",
  "ar": "أكسدة",
  "cs": "Oxidace",
  "da": "Oxidation",
  "de": "Oxidation",
  "el": "Οξείδωση",
  "es-419": "Oxidación",
  "es-ES": "Oxidación",
  "es": "Oxidación",
  "fi": "Hapetus",
  "fr": "Oxydation",
  "he": "חמצון",
  "hr": "Oksidacija",
  "hu": "Oxidáció",
  "id": "Oksidasi",
  "it": "Ossidazione",
  "ja": "酸化",
  "ko": "산화",
  "lv": "Oksidēšana",
  "nb": "Oksidasjon",
  "nl": "Oxidatie",
  "pl": "Utlenianie",
  "pt-BR": "Oxidação",
  "pt-PT": "Oxidação",
  "ro": "Oxidare",
  "ru": "Окисление",
  "sk": "Oxidácia",
  "sl": "Oksidacija",
  "sv": "Oxidation",
  "th": "ออกซิเดชัน",
  "tr": "Oksidasyon",
  "uk": "Окиснення",
  "vi": "Oxy hóa",
  "zh-Hans": "氧化",
  "zh": "氧化"
}
Starting Material

c1ccccc1C=O

Product

c1ccccc1CO.c1ccccc1C(=O)[O-]

Reagents

NaOH (conc.), KOH

Conditions
{
  "en": "Strong base, no α-hydrogens",
  "ar": "قوي قاعدة, لا α-هيدروجينات",
  "cs": "Silna baze, bez α-hydrogens",
  "da": "Stærk base, no α-hydrogens",
  "de": "Stark Base, no α-hydrogens",
  "el": "Ισχυρή βάση, όχι α-hydrogens",
  "es-419": "Base fuerte, no α-hydrogens",
  "es-ES": "Base fuerte, no α-hydrogens",
  "es": "Base fuerte, no α-hydrogens",
  "fi": "Vahva emäs, no α-hydrogens",
  "fr": "Base forte, no α-hydrogens",
  "he": "חזק בסיס, אין α-מימנים",
  "hr": "Jaka baza, bez α-hydrogens",
  "hu": "Erős bázis, nbancs α-hydrogens",
  "id": "Basa kuat, tanpa α-hidrogen",
  "it": "Base forte, no α-hydrogens",
  "ja": "強塩基、α-水素なし",
  "ko": "강염기, α-수소 없음",
  "lv": "Stipra baze, nav α-hydrogens",
  "nb": "Sterk base, no α-hydrogens",
  "nl": "Sterk base, no α-hydrogens",
  "pl": "Silna zasada, brak α-hydrogens",
  "pt-BR": "Base forte, no α-hydrogens",
  "pt-PT": "Base forte, no α-hydrogens",
  "ro": "Bază puternică, no α-hydrogens",
  "ru": "Сильное основание, нет α-hydrogens",
  "sk": "Silna baza, bez α-hydrogens",
  "sl": "Mocna baza, brez α-hydrogens",
  "sv": "Stark bas, no α-hydrogens",
  "th": "เบสแรง, ไม่มีไฮโดรเจนตำแหน่ง α",
  "tr": "Güçlü baz, α-hidrojen yok",
  "uk": "Сильна основа, немає α-hydrogens",
  "vi": "Bazơ mạnh, không có α-hydrogen",
  "zh-Hans": "强碱,无 α-氢",
  "zh": "强碱,无 α-氢"
}
Mechanism
[
  {
    "smiles": "c1ccccc1C=O",
    "description": {
      "en": "Benzaldehyde: no α-hydrogens (cannot enolize)",
      "ar": "Benzaldehyde: لا α-هيدروجينات (cannot enolize)",
      "cs": "Benzaldehyde: bez α-hydrogens (cannot enolize)",
      "da": "Benzaldehyd: no α-hydrogens (cannot enolize)",
      "de": "Benzaldehyd: no α-hydrogens (cannot enolize)",
      "el": "Benzaldehyde: όχι α-hydrogens (canόχι eόχιlize)",
      "es-419": "Benzaldehído: sin hidrógenos α (no puede enolizar)",
      "es-ES": "Benzaldehído: sin hidrógenos α (no puede enolizar)",
      "es": "Benzaldehído: sin hidrógenos α (no puede enolizar)",
      "fi": "Bentsaldehydi: no α-hydrogens (cannot enolize)",
      "fr": "Benzaldéhyde: pas d’hydrogènes α (ne peut pas s’énoliser)",
      "he": "Benzaldehyde: אין α-מימנים (cannot enolize)",
      "hr": "Benzaldehyde: bez α-hydrogens (cannot enolize)",
      "hu": "Benzaldehyde: nbancs α-hydrogens (cannem enbancslize)",
      "id": "Benzaldehida: tidak ada α-hidrogen (tidak dapat berenolisasi)",
      "it": "Benzaldeide: nessun idrogeno α (non può enolizzare)",
      "ja": "ベンズアルデヒド: α-水素がない(エノール化できない)",
      "ko": "벤즈알데하이드: α-수소가 없음(엔올화 불가)",
      "lv": "Benzaldehyde: nav α-hydrogens (cannot enolize)",
      "nb": "Benzaldehyd: no α-hydrogens (cannot enolize)",
      "nl": "Benzaldehyde: geen α-waterstoffen (kan niet enoliseren)",
      "pl": "Benzaldehyde: brak α-hydrogens (cannot enolize)",
      "pt-BR": "Benzaldeído: sem hidrogênios α (não pode enolizar)",
      "pt-PT": "Benzaldeído: sem hidrogênios α (não pode enolizar)",
      "ro": "Benzaldehidă: fără hidrogeni α (nu poate enoliza)",
      "ru": "Benzaldehyde: нет α-hydrogens (cannot enolize)",
      "sk": "Benzaldehyde: bez α-hydrogens (cannot enolize)",
      "sl": "Benzaldehyde: brez α-hydrogens (cannot enolize)",
      "sv": "Bensaldehyd: no α-hydrogens (cannot enolize)",
      "th": "เบนซัลดีไฮด์: ไม่มีไฮโดรเจนตำแหน่ง α (จึงเกิดอีนอลไม่ได้)",
      "tr": "Benzaldehyde: α-hidrojen yok (cveeğil eyoklize)",
      "uk": "Benzaldehyde: немає α-hydrogens (cannot enolize)",
      "vi": "Benzaldehyde: không có α-hydrogen (không thể enol hóa)",
      "zh-Hans": "苯甲醛:无 α-氢(不能烯醇化)",
      "zh": "苯甲醛:无 α-氢(不能烯醇化)"
    }
  },
  {
    "smiles": "c1ccccc1C=O",
    "description": {
      "en": "OH⁻ attacks carbonyl, hydride transfers to another aldehyde",
      "ar": "OH⁻ يهاجم كربونيل, هيدريد transfers إلى آخر ألدهيد",
      "cs": "OH⁻ utoci karbonyl, hydrid transfers na another aldehyd",
      "da": "OH⁻ angriber carbonyl, hydride transfers til another aldehyd",
      "de": "OH⁻ greift an Carbonyl, hydride transfers zu another Aldehyd",
      "el": "OH⁻ επιτίθεται καρβονύλιο, hydride transfers σε aόχιher αλδεΰδη",
      "es-419": "OH⁻ ataca carbonoyl, hidruro transfers a another aldehído",
      "es-ES": "OH⁻ ataca carbonoyl, hidruro transfers a another aldehído",
      "es": "OH⁻ ataca carbonoyl, hidruro transfers a another aldehído",
      "fi": "OH⁻ hyökkää karbonyyli, hydride transfers kohti another aldehydi",
      "fr": "OH⁻ attaque carboneyl, hydrure transfers en another aldéhyde",
      "he": "OH⁻ תוקף קרבוניל, הידריד transfers ל אחר אלדהיד",
      "hr": "OH⁻ napada karbonil, hidrid transfers u another aldehid",
      "hu": "OH⁻ támad karbonil, hydride transfers to anemher aldehid",
      "id": "OH⁻ menyerang karbonil, hidrida berpindah ke aldehida lain",
      "it": "OH⁻ attacca carbonioyl, idruro transfers a another aldeide",
      "ja": "OH⁻がカルボニルを攻撃し、ヒドリドが別のアルデヒドへ移動する",
      "ko": "OH⁻가 카보닐을 공격하고, 하이드라이드가 다른 알데하이드로 이동함",
      "lv": "OH⁻ uzbruk karbonils, hidrids transfers uz another aldehids",
      "nb": "OH⁻ angriper karbonyl, hydride transfers til another aldehyd",
      "nl": "OH⁻ valt aan carbonyl, hydride transfers tot another aldehyde",
      "pl": "OH⁻ atakuje karbonyl, wodorek transfers do another aldehyd",
      "pt-BR": "OH⁻ ataca carbonoyl, hidreto transfers a another aldeído",
      "pt-PT": "OH⁻ ataca carbonoyl, hidreto transf...
Tips
[
  {
    "en": "Disproportionation: 2 aldehydes → 1 alcohol + 1 carboxylate",
    "ar": "Disproportionation: 2 ألدهيدات → 1 كحول + 1 كربوكسيلات",
    "cs": "Disproportionation: 2 aldehydy → 1 alkohol + 1 karboxylat",
    "da": "Disproportionation: 2 aldehydes → 1 alkohol + 1 carboxylate",
    "de": "Disproportionation: 2 aldehydes → 1 Alkohol + 1 carboxylate",
    "el": "Dispropήtiσεσεiσε: 2 αλδεΰδες → 1 αλκοόλη + 1 carboxylσεe",
    "es-419": "Disproportionation: 2 aldehídos → 1 alcohol + 1 carboxylate",
    "es-ES": "Disproportionation: 2 aldehídos → 1 alcohol + 1 carboxylate",
    "es": "Disproportionation: 2 aldehídos → 1 alcohol + 1 carboxylate",
    "fi": "Disproportionation: 2 aldehydes → 1 alkoholi + 1 carboxylate",
    "fr": "Disproportionation: 2 aldéhydes → 1 alcool + 1 carboxylate",
    "he": "Disproportionation: 2 אלדהידים → 1 אלכוהול + 1 קרבוקסילט",
    "hr": "Disproportionation: 2 aldehidi → 1 alkohol + 1 karboksilat",
    "hu": "Dispropvagytionnálion: 2 aldehidek → 1 alkohol + 1 carboxylnále",
    "id": "Disproporsionasi: 2 aldehida → 1 alkohol + 1 karboksilat",
    "it": "Disproportionation: 2 aldeidi → 1 alcol + 1 carboxylate",
    "ja": "不均化: 2つのアルデヒド → 1つのアルコール + 1つのカルボキシラート",
    "ko": "불균등화: 알데하이드 2개 → 알코올 1개 + 카복실레이트 1개",
    "lv": "Disproportionation: 2 aldehidi → 1 spirts + 1 karboksilats",
    "nb": "Disproportionation: 2 aldehydes → 1 alkohol + 1 carboxylate",
    "nl": "Disproportionering: 2 aldehyden → 1 alcohol + 1 carboxylaat",
    "pl": "Disproportionation: 2 aldehydy → 1 alkohol + 1 karboksylan",
    "pt-BR": "Disproportionation: 2 aldeídos → 1 álcool + 1 carboxylate",
    "pt-PT": "Disproportionation: 2 aldeídos → 1 álcool + 1 carboxylate",
    "ro": "Disproportionation: 2 aldehide → 1 alcool + 1 carboxylate",
    "ru": "Disproportionation: 2 альдегиды → 1 спирт + 1 карбоксилат",
    "sk": "Disproportionation: 2 aldehydy → 1 alkohol + 1 karboxylat",
    "sl": "Disproportionation: 2 aldehidi → 1 alkohol + 1 karboksilat",
    "sv": "Disproportionation: 2 aldehydes → 1 alkohol + 1 carboxylate",
    "th": "ดิสพรอพอร์ชันเนชัน: แอลดีไฮด์ 2 โมเลกุล → แอลกอฮอล์ 1 + คาร์บอกซิเลต 1",
    "tr": "Dispropveyolarakiyüzerinde: 2 aldehit → 1 alkol + 1 karboksilde",
    "uk": "Disproportionation: 2 альдегіди → 1 спирт + 1 карбоксилат",
    "vi": "Phản ứng tự oxy hóa-khử: 2 aldehit → 1 ancol + 1 carboxylate",
    "zh-Hans": "歧化:2 个醛 → 1 个醇 + 1 个羧酸盐",
    "zh": "歧化:2 个醛 → 1 个醇 + 1 个羧酸盐"
  },
  {
    "en": "Only for aldehydes WITHOUT α-hydrogens",
    "ar": "Only لـ ألدهيدات WITHOUT α-هيدروجينات",
    "cs": "Only pro aldehydy WITHOUT α-hydrogens",
    "da": "Kun for aldehyder UDEN α-hydrogener",
    "de": "Nur für Aldehyde OHNE α-Wasserstoffe",
    "el": "Μόνο για αλδεΰδες WITHOUT α-hydrogens",
    "es-419": "Only para aldehídos SIN α-hydrogens",
    "es-ES": "Only para aldehídos SIN α-hydrogens",
    "es": "Only para aldehídos SIN α-hydrogens",
    "fi": "Vain aldehydeille ILMAN α-vetyjä",
    "fr": "Only pour aldéhydes SANS α-hydrogens",
    "he": "Only עבור אלדהידים WITHOUT α-מימנים",
    "hr": "Only za aldehidi WITHOUT α-hydrogens",
    "hu": "Csak számára aldehidek WITHOUT α-hydrogens",
    "id": "Hanya untuk aldehida TANPA α-hidrogen",
    "it": "Only per aldeidi SENZA α-hydrogens",
    "ja": "α-水素を持たないアルデヒドでのみ進行",
    "ko": "α-수소가 없는 알데하이드에서만 일어남",
    "lv": "Only prieks aldehidi WITHOUT α-hydrogens",
    "nb": "Bare for aldehyder UTEN α-hydrogener",
    "nl": "Alleen voor aldehyden ZONDER α-waterstoffen",
    "pl": "Only dla aldehydy WITHOUT α-hydrogens",
    "pt-BR": "Only para aldeídos SEM α-hydrogens",
    "pt-PT": "Only para aldeídos SEM α-hydrogens",
    "ro": "Only pentru aldehide FĂRĂ α-hydrogens",
    "ru": "Only для альдегиды WITHOUT α-hydrogens",
    "sk": "Only pre aldehydy WITHOUT α-hydrogens",
    "sl": "Only za aldehidi WITHOUT α-hydrogens",
    "sv": "Endast för aldehyder UTAN α-väten",
    "th": "ใช้ได้เฉพาะแอลดีไฮด์ที่ไม่มีไฮโดรเจนตำแหน่ง α",
    "tr": "Yalnızca α-hidrojeni olmayan alde...
Related Reactions

aldol-addition

Is Free

false