Octet / Reactions

Pinacol Rearrangement

Included in Reactions.

Rearrangement

Source Details

Id

pinacol-rearrangement

Name
{
  "en": "Pinacol Rearrangement",
  "ar": "Pinacol إعادة ترتيب",
  "cs": "Pinacol Presmyk",
  "da": "Pinacol Omlejring",
  "de": "Pinacol Umlagerung",
  "el": "Pσεacol Αναδιάταξη",
  "es-419": "Reordenamiento pinacolique",
  "es-ES": "Reordenamiento pinacolique",
  "es": "Reordenamiento pinacolique",
  "fi": "Pinacol Uudelleenjärjestyminen",
  "fr": "Réarrangement pinacolique",
  "he": "Pinacol סידור מחדש",
  "hr": "Pinacol Pregrađivanje",
  "hu": "Pbanacol Átrendeződés",
  "id": "Penataan Ulang Pinakol",
  "it": "Riarrangiamento pinacolique",
  "ja": "Pinacol転位",
  "ko": "Pinacol 재배열",
  "lv": "Pinacol Pargrupesanas",
  "nb": "Pinacol Omleiring",
  "nl": "Pinacol Omlegging",
  "pl": "Pinacol Przegrupowanie",
  "pt-BR": "Rearranjo pinacolique",
  "pt-PT": "Rearranjo pinacolique",
  "ro": "Rearanjare pinacolique",
  "ru": "Pinacol Перегруппировка",
  "sk": "Pinacol Prestavba",
  "sl": "Pinacol Preureditev",
  "sv": "Pinacol Omarrangering",
  "th": "การจัดเรียงใหม่แบบ Pinacol",
  "tr": "Piçindeacol Yeniden düzenlenme",
  "uk": "Pinacol Перегрупування",
  "vi": "Tái sắp xếp pinacol",
  "zh-Hans": "Pinacol 重排",
  "zh": "Pinacol 重排"
}
Type
{
  "en": "Rearrangement",
  "ar": "إعادة ترتيب",
  "cs": "Přesmyk",
  "da": "Omlejring",
  "de": "Umlagerung",
  "el": "Αναδιάταξη",
  "es-419": "Transposición",
  "es-ES": "Reordenamiento",
  "es": "Transposición",
  "fi": "Uudelleenjärjestyminen",
  "fr": "Réarrangement",
  "he": "סידור מחדש",
  "hr": "Pregradnja",
  "hu": "Átrendeződés",
  "id": "Penataan ulang",
  "it": "Riarrangiamento",
  "ja": "転位",
  "ko": "자리옮김",
  "lv": "Pārkārtošanās",
  "nb": "Omleiring",
  "nl": "Herschikking",
  "pl": "Przegrupowanie",
  "pt-BR": "Rearranjo",
  "pt-PT": "Rearranjo",
  "ro": "Rearanjare",
  "ru": "Перегруппировка",
  "sk": "Prešmyk",
  "sl": "Preureditev",
  "sv": "Omlagring",
  "th": "การจัดเรียงใหม่",
  "tr": "Yeniden düzenlenme",
  "uk": "Перегрупування",
  "vi": "Tái sắp xếp",
  "zh-Hans": "重排",
  "zh": "重排"
}
Starting Material

CC(O)(C)C(O)(C)C

Product

CC(=O)C(C)(C)C

Reagents

H₂SO₄, H₃PO₄

Conditions
{
  "en": "Acidic conditions, heat",
  "ar": "شروط حمضية, تسخين",
  "cs": "Kysele podminky, zahrivani",
  "da": "Acidic conditions, varme",
  "de": "Acidic conditions, Hitze",
  "el": "Acidic συνθήκες, θέρμανση",
  "es-419": "Acidic condiciones, heat",
  "es-ES": "Acidic condiciones, heat",
  "es": "Acidic condiciones, heat",
  "fi": "Acidic conditions, lämpö",
  "fr": "Conditions acides, chaleur",
  "he": "תנאים חומציים, חימום",
  "hr": "Kiseo uvjeti, toplina",
  "hu": "Acidic körülmények, hő",
  "id": "Kondisi asam, panas",
  "it": "Acidic condizioni, heat",
  "ja": "酸性条件、加熱",
  "ko": "산성 조건, 열",
  "lv": "Skabs apstakli, sildisana",
  "nb": "Acidic conditions, varme",
  "nl": "Acidic conditions, warmte",
  "pl": "Kwasowy warunki, ogrzewanie",
  "pt-BR": "Acidic condições, heat",
  "pt-PT": "Acidic condições, heat",
  "ro": "Acidic condiții, heat",
  "ru": "Кислый условия, нагрев",
  "sk": "Kysly podmienky, zahrievanie",
  "sl": "Kisel pogoji, segrevanje",
  "sv": "Acidic conditions, värme",
  "th": "สภาวะกรด, ความร้อน",
  "tr": "Asidik koşullar, ısı",
  "uk": "Кислий умови, нагрівання",
  "vi": "Điều kiện axit, nhiệt",
  "zh-Hans": "酸性条件,加热",
  "zh": "酸性条件,加热"
}
Mechanism
[
  {
    "smiles": "CC(O)(C)C(O)(C)C",
    "description": {
      "en": "Pinacol: 1,2-diol (vic-diol)",
      "ar": "Pinacol: 1,2-ديول (vic-diol)",
      "cs": "Pinakol: 1,2-diol (vic-diol)",
      "da": "Pinacol: 1,2-diol (vicinal diol)",
      "de": "Pinacol: 1,2-Diol (vic-Diol)",
      "el": "Pσεacol: 1,2-diol (vic-diol)",
      "es-419": "Pinacol: 1,2-diol (diol vecinal)",
      "es-ES": "Pinacol: 1,2-diol (diol vecinal)",
      "es": "Pinacol: 1,2-diol (diol vecinal)",
      "fi": "Pinakoli: 1,2-dioli (vic-dioli)",
      "fr": "Pinacol: 1,2-diol (diol vicinal)",
      "he": "Pinacol: 1,2-דיול (vic-diol)",
      "hr": "Pinakol: 1,2-diol (vic-diol)",
      "hu": "Pbanacol: 1,2-diol (vic-diol)",
      "id": "Pinakol: 1,2-diol (vic-diol)",
      "it": "Pinacolo: 1,2-diolo (diolo vicinale)",
      "ja": "ピナコール: 1,2-ジオール(vic-ジオール)",
      "ko": "피나콜: 1,2-다이올(vic-다이올)",
      "lv": "Pinakols: 1,2-diols (vic-diols)",
      "nb": "Pinakol: 1,2-diol (vic-diol)",
      "nl": "Pinacol: 1,2-diol (vic-diol)",
      "pl": "Pinakol: 1,2-diol (vic-diol)",
      "pt-BR": "Pinacol: 1,2-diol (diol vicinal)",
      "pt-PT": "Pinacol: 1,2-diol (diol vicinal)",
      "ro": "Pinacol: 1,2-diol (diol vicinal)",
      "ru": "Пинакол: 1,2-диол (vic-диол)",
      "sk": "Pinakol: 1,2-diol (vic-diol)",
      "sl": "Pinakol: 1,2-diol (vic-diol)",
      "sv": "Pinakol: 1,2-diol (vic-diol)",
      "th": "พินาคอล: 1,2-ไดออล (ไดออลข้างเคียง)",
      "tr": "Piçindeacol: 1,2-diol (vic-diol)",
      "uk": "Пінакол: 1,2-діол (vic-діол)",
      "vi": "Pinacol: 1,2-diol (vic-diol)",
      "zh-Hans": "频哪醇:1,2-二醇(邻二醇)",
      "zh": "频哪醇:1,2-二醇(邻二醇)"
    }
  },
  {
    "smiles": "CC(O)(C)C(O)(C)C",
    "description": {
      "en": "Protonation of one OH, water leaves → carbocation",
      "ar": "بروتنة من واحدة OH, الماء يغادر → كربوكاتيون",
      "cs": "Protonation z jeden OH, voda odchazi → karbokation",
      "da": "Protonation of one OH, vand forlader → carbokation",
      "de": "Protonation of one OH, Wasser geht ab → Carbokation",
      "el": "Protσεσεiσε της ένα OH, νερό αποχωρεί → καρβοκατιόν",
      "es-419": "Protonación of uno OH, agua sale → carbocatión",
      "es-ES": "Protonación of uno OH, agua sale → carbocatión",
      "es": "Protonación of uno OH, agua sale → carbocatión",
      "fi": "Protonation of one OH, vesi lähtee → karbokationi",
      "fr": "Protonation of un OH, eau part → carbocation",
      "he": "פרוטונציה של אחת OH, מים עוזב → קרבוקציון",
      "hr": "Protonation od jedan OH, voda odlazi → karbokation",
      "hu": "Protonnálion of egy OH, víz kilép → karboknálion",
      "id": "Protonasi salah satu OH, air pergi → karbokation",
      "it": "Protonazione of uno OH, acqua esce → carbocatione",
      "ja": "一方のOHがプロトン化され、水が脱離する → カルボカチオン",
      "ko": "한 OH가 양성자화되고 물이 떠남 → 탄소양이온",
      "lv": "Protonation nav viens OH, udens aiziet → karbokations",
      "nb": "Protonation of one OH, vann forlater → karbokation",
      "nl": "Protonation of one OH, water vertrekt → carbokation",
      "pl": "Protonation z jeden OH, woda odchodzi → karbokation",
      "pt-BR": "Protonação of um OH, água sai → carbocátion",
      "pt-PT": "Protonação of um OH, água sai → carbocátion",
      "ro": "Protonare of unul OH, apă pleacă → carbocation",
      "ru": "Protonation из один OH, вода уходит → карбокатион",
      "sk": "Protonation z jeden OH, voda odchadza → karbokation",
      "sl": "Protonation od en OH, voda odide → karbokation",
      "sv": "Protonation of one OH, vatten lämnar → karbokatjon",
      "th": "OH หนึ่งตัวถูกโปรตอนเนต น้ำออกไป → คาร์โบแคตไอออน",
      "tr": "Bir OH protüzerindelanır, su ayrılır → karbokdeyüzerinde",
      "uk": "Protonation з один OH, вода відходить → карбокатіон",
      "vi": "Proton hóa một OH, nước rời đi → carbocation",
      "zh-Hans": "一个 OH 质子化,水离去 → 碳正离子",
      "zh": "一个 OH 质子化,水离去 → 碳正离子"
    }
  },
  {
    "smiles": "CC(=O)C(C)(C)C",
    "description": {
      "en": "1,2-methyl shift gives more stable catio...
Tips
[
  {
    "en": "1,2-Diol → Ketone (or aldehyde)",
    "ar": "1,2-Diol → كيتون (أو ألدهيد)",
    "cs": "1,2-Diol → Keton (nebo aldehyd)",
    "da": "1,2-Diol → Keton (eller aldehyd)",
    "de": "1,2-Diol → Keton (oder Aldehyd)",
    "el": "1,2-Diol → Κετόνη (ή αλδεΰδη)",
    "es-419": "1,2-Diol → Cetona (o aldehído)",
    "es-ES": "1,2-Diol → Cetona (o aldehído)",
    "es": "1,2-Diol → Cetona (o aldehído)",
    "fi": "1,2-Diol → Ketoni (tai aldehydi)",
    "fr": "1,2-Diol → Cétone (ou aldéhyde)",
    "he": "1,2-Diol → קטון (או אלדהיד)",
    "hr": "1,2-Diol → Keton (ili aldehid)",
    "hu": "1,2-Diol → Keton (vagy aldehid)",
    "id": "1,2-Diol → Keton (atau aldehida)",
    "it": "1,2-Diol → Chetone (o aldeide)",
    "ja": "1,2-ジオール → ケトン(またはアルデヒド)",
    "ko": "1,2-다이올 → 케톤(또는 알데하이드)",
    "lv": "1,2-Diol → Ketons (vai aldehids)",
    "nb": "1,2-Diol → Keton (eller aldehyd)",
    "nl": "1,2-Diol → Keton (of aldehyde)",
    "pl": "1,2-Diol → Keton (lub aldehyd)",
    "pt-BR": "1,2-Diol → Cetona (ou aldeído)",
    "pt-PT": "1,2-Diol → Cetona (ou aldeído)",
    "ro": "1,2-Diol → Cetonă (sau aldehidă)",
    "ru": "1,2-Diol → Кетон (или альдегид)",
    "sk": "1,2-Diol → Keton (alebo aldehyd)",
    "sl": "1,2-Diol → Keton (ali aldehid)",
    "sv": "1,2-Diol → Keton (eller aldehyd)",
    "th": "1,2-ไดออล → คีโตน (หรือแอลดีไฮด์)",
    "tr": "1,2-Diol → Ketüzerinde (veya aldehit)",
    "uk": "1,2-Diol → Кетон (або альдегід)",
    "vi": "1,2-diol → xeton (hoặc aldehit)",
    "zh-Hans": "1,2-二醇 → 酮(或醛)",
    "zh": "1,2-二醇 → 酮(或醛)"
  },
  {
    "en": "Migration to carbocation center",
    "ar": "Migration إلى كربوكاتيون مركز",
    "cs": "Migration na karbokation center",
    "da": "Migration til carbokation center",
    "de": "Migration zu Carbokation center",
    "el": "Migrσεiσε σε καρβοκατιόν center",
    "es-419": "Migration a carbocatión centro",
    "es-ES": "Migration a carbocatión centro",
    "es": "Migration a carbocatión centro",
    "fi": "Migration kohti karbokationi center",
    "fr": "Migration en carbocation centre",
    "he": "Migration ל קרבוקציון מרכז",
    "hr": "Migration u karbokation center",
    "hu": "Migrnálion to karboknálion center",
    "id": "Migrasi ke pusat karbokation",
    "it": "Migration a carbocatione centro",
    "ja": "カルボカチオン中心へ移動する",
    "ko": "탄소양이온 중심으로 이동함",
    "lv": "Migration uz karbokations center",
    "nb": "Migration til karbokation center",
    "nl": "Migration tot carbokation center",
    "pl": "Migration do karbokation center",
    "pt-BR": "Migration a carbocátion centro",
    "pt-PT": "Migration a carbocátion centro",
    "ro": "Migration la carbocation centru",
    "ru": "Migration в карбокатион center",
    "sk": "Migration na karbokation center",
    "sl": "Migration v karbokation center",
    "sv": "Migration till karbokatjon center",
    "th": "การย้ายไปยังศูนย์คาร์โบแคตไอออน",
    "tr": "Karbokdeyüzerinde merkeziçindee göç",
    "uk": "Migration до карбокатіон center",
    "vi": "Di chuyển về tâm carbocation",
    "zh-Hans": "向碳正离子中心迁移",
    "zh": "向碳正离子中心迁移"
  },
  {
    "en": "More substituted group usually migrates",
    "ar": "أكثر مستبدل مجموعة عادة يهاجر",
    "cs": "Vice substituovany skupina usually migruje",
    "da": "More substitueret gruppe usually migrates",
    "de": "More substituiert Gruppe usually migrates",
    "el": "Περισσότερο υποκατεστημένο ομάδα usually migrσεes",
    "es-419": "Más substituted group normalmente migrates",
    "es-ES": "Más substituted group normalmente migrates",
    "es": "Más substituted group normalmente migrates",
    "fi": "More substituoitu ryhmä usually migrates",
    "fr": "Plus substituted group habituellement migrates",
    "he": "יותר מותמר קבוצה בדרך כלל נודד",
    "hr": "Vise supstituiran skupina usually migrira",
    "hu": "Több szubsztituált csopvagyt usually migrnáles",
    "id": "Gugus yang lebih tersubstitusi biasanya bermigrasi",
    "it": "Più substituted group di solito migrates",
    "ja": "通常、より置換度の高い基が移動する",
    "...
Related Reactions

Is Free

false