Octet / Reactions

Hydroboration-Oxidation

Included in Reactions.

Addition

Source Details

Id

hydroboration

Name
{
  "en": "Hydroboration-Oxidation",
  "ar": "الهيدروبورة-أكسدة",
  "cs": "Hydroboration-Oxidace",
  "da": "Hydroboration-Oxidation",
  "de": "Hydroboration-Oxidation",
  "el": "Hydrobήσεiσε-Οξείδωση",
  "es-419": "Hydroboration-oxydation",
  "es-ES": "Hydroboration-oxydation",
  "es": "Hydroboration-oxydation",
  "fi": "Hydroboration-Hapetus",
  "fr": "Hydroboration-oxydation",
  "he": "הידרובורציה-חמצון",
  "hr": "Hydroboration-Oksidacija",
  "hu": "Hydrobvagynálion-Oxidáció",
  "id": "Hidroborasi-Oksidasi",
  "it": "Hydroboration-oxydation",
  "ja": "ヒドロホウ素化-酸化",
  "ko": "하이드로보레이션-산화",
  "lv": "Hydroboration-Oksidesana",
  "nb": "Hydroboration-Oksidasjon",
  "nl": "Hydroboration-Oxidatie",
  "pl": "Hydroboration-Utlenianie",
  "pt-BR": "Hydroboration-oxydation",
  "pt-PT": "Hydroboration-oxydation",
  "ro": "Hydroboration-oxydation",
  "ru": "Hydroboration-Окисление",
  "sk": "Hydroboration-Oxidacia",
  "sl": "Hydroboration-Oksidacija",
  "sv": "Hydroboration-Oxidation",
  "th": "ไฮโดรโบเรชัน-ออกซิเดชัน",
  "tr": "Hydrobveyadeiüzerinde-Oksidolarakyüzerinde",
  "uk": "Hydroboration-Окиснення",
  "vi": "Hydroboration-oxy hóa",
  "zh-Hans": "硼氢化-氧化",
  "zh": "硼氢化-氧化"
}
Type
{
  "en": "Addition",
  "ar": "إضافة",
  "cs": "Adice",
  "da": "Addition",
  "de": "Addition",
  "el": "Προσθήκη",
  "es-419": "Adición",
  "es-ES": "Adición",
  "es": "Adición",
  "fi": "Additio",
  "fr": "Addition",
  "he": "סיפוח",
  "hr": "Adicija",
  "hu": "Addíció",
  "id": "Adisi",
  "it": "Addizione",
  "ja": "付加",
  "ko": "첨가",
  "lv": "Pievienošana",
  "nb": "Addisjon",
  "nl": "Additie",
  "pl": "Addycja",
  "pt-BR": "Adição",
  "pt-PT": "Adição",
  "ro": "Adiție",
  "ru": "Присоединение",
  "sk": "Adícia",
  "sl": "Adicija",
  "sv": "Addition",
  "th": "การเติม",
  "tr": "Katılma",
  "uk": "Приєднання",
  "vi": "Cộng",
  "zh-Hans": "加成",
  "zh": "加成"
}
Subtype
{
  "en": "Syn Addition",
  "ar": "إضافة متزامنة",
  "cs": "Syn adice",
  "da": "Syn-addition",
  "de": "Syn-Addition",
  "el": "Syn προσθήκη",
  "es-419": "Adición syn",
  "es-ES": "Adición syn",
  "es": "Adición syn",
  "fi": "Syn-additio",
  "fr": "Addition syn",
  "he": "סיפוח syn",
  "hr": "Syn adicija",
  "hu": "Syn addíció",
  "id": "Adisi syn",
  "it": "Addizione sin",
  "ja": "syn付加",
  "ko": "syn 첨가",
  "lv": "Syn adīcija",
  "nb": "Syn-addisjon",
  "nl": "Syn-additie",
  "pl": "Addycja syn",
  "pt-BR": "Adição syn",
  "pt-PT": "Adição syn",
  "ro": "Adiție syn",
  "ru": "Син-присоединение",
  "sk": "Syn adícia",
  "sl": "Syn adicija",
  "sv": "Syn-addition",
  "th": "การเติมแบบ syn",
  "tr": "Syn katılma",
  "uk": "Син-приєднання",
  "vi": "Cộng syn",
  "zh-Hans": "顺式加成",
  "zh": "顺式加成"
}
Starting Material

CC=C

Product

CCCO

Reagents

BH₃·THF, then H₂O₂/NaOH

Conditions
{
  "en": "THF solvent, 0°C for BH₃, then oxidation",
  "ar": "THF مذيب, 0°C لـ BH₃, ثم أكسدة",
  "cs": "THF rozpoustedlo, 0°C pro BH₃, potom oxidace",
  "da": "THF opløsningsmiddel, 0°C for BH₃, then oxidation",
  "de": "THF Lösungsmittel, 0°C for BH₃, then oxidation",
  "el": "THF διαλύτης, 0°C για BH₃, έπειτα οξείδωση",
  "es-419": "Solvente THF, 0 °C para BH₃, luego oxidación",
  "es-ES": "Solvente THF, 0 °C para BH₃, luego oxidación",
  "es": "Solvente THF, 0 °C para BH₃, luego oxidación",
  "fi": "THF liuotin, 0°C for BH₃, then oxidation",
  "fr": "Solvant THF, 0 °C pour BH₃, puis oxydation",
  "he": "THF ממס, 0°C עבור BH₃, ואז חמצון",
  "hr": "THF otapalo, 0°C za BH₃, zatim oksidacija",
  "hu": "THF oldószer, 0°C BH₃ esetén, majd oxidáció",
  "id": "Pelarut THF, 0°C untuk BH₃, lalu oksidasi",
  "it": "Solvente THF, 0 °C per BH₃, poi ossidazione",
  "ja": "THF溶媒、BH₃は0°C、その後酸化",
  "ko": "THF 용매, BH₃는 0°C, 이후 산화",
  "lv": "THF skidinatajs, 0°C prieks BH₃, pec tam oksidesana",
  "nb": "THF løsemiddel, 0°C for BH₃, then oxidation",
  "nl": "THF oplosmiddel, 0°C for BH₃, then oxidation",
  "pl": "THF rozpuszczalnik, 0°C dla BH₃, nastepnie utlenianie",
  "pt-BR": "Solvente THF, 0 °C para BH₃, depois oxidação",
  "pt-PT": "Solvente THF, 0 °C para BH₃, depois oxidação",
  "ro": "Solvent THF, 0 °C pentru BH₃, apoi oxidare",
  "ru": "THF растворитель, 0°C для BH₃, затем окисление",
  "sk": "THF rozpustadlo, 0°C pre BH₃, potom oxidacia",
  "sl": "THF topilo, 0°C za BH₃, nato oksidacija",
  "sv": "THF lösningsmedel, 0°C for BH₃, then oxidation",
  "th": "ตัวทำละลาย THF, 0°C สำหรับ BH₃ จากนั้นออกซิเดชัน",
  "tr": "THF çözücü, BH₃ içiçinde 0°C, ardından oksidolarakyüzerinde",
  "uk": "THF розчинник, 0°C для BH₃, потім окиснення",
  "vi": "Dung môi THF, 0°C cho BH₃, sau đó oxy hóa",
  "zh-Hans": "THF 溶剂,BH₃ 在 0°C,然后氧化",
  "zh": "THF 溶剂,BH₃ 在 0°C,然后氧化"
}
Mechanism
[
  {
    "smiles": "CC=C",
    "description": {
      "en": "Propene",
      "ar": "بروبين",
      "cs": "Propen",
      "da": "Propene",
      "de": "Propene",
      "el": "Προπένιο",
      "es-419": "Propene",
      "es-ES": "Propene",
      "es": "Propene",
      "fi": "Propene",
      "fr": "Propene",
      "he": "פרופן",
      "hr": "Propen",
      "hu": "Propén",
      "id": "Propena",
      "it": "Propene",
      "ja": "プロペン",
      "ko": "프로펜",
      "lv": "Propens",
      "nb": "Propene",
      "nl": "Propene",
      "pl": "Propen",
      "pt-BR": "Propene",
      "pt-PT": "Propene",
      "ro": "Propene",
      "ru": "Пропен",
      "sk": "Propen",
      "sl": "Propen",
      "sv": "Propene",
      "th": "โพรพีน",
      "tr": "Propen",
      "uk": "Пропен",
      "vi": "Propen",
      "zh-Hans": "丙烯",
      "zh": "丙烯"
    }
  },
  {
    "smiles": "CCCB",
    "description": {
      "en": "BH₃ adds across double bond in single step (concerted, syn)",
      "ar": "BH₃ يضيف عبر مزدوجة رابطة في واحدة خطوة (متزامن, syn)",
      "cs": "BH₃ pridava se across dvojna vazba v jeden krok (concerted, syn)",
      "da": "BH₃ adds across double binding in ét trin (concerted, syn)",
      "de": "BH₃ adds across double Bindung in ein Schritt (concerted, syn)",
      "el": "BH₃ προστίθεται κατά μήκος του διπλού δεσμού σε ένα βήμα (συγχρονισμένη, syn)",
      "es-419": "BH₃ se añade across doble enlace en un solo paso (concerted, syn)",
      "es-ES": "BH₃ se añade across doble enlace en un solo paso (concerted, syn)",
      "es": "BH₃ se añade across doble enlace en un solo paso (concerted, syn)",
      "fi": "BH₃ adds across double sidos in yksi vaihe (concerted, syn)",
      "fr": "BH₃ s'ajoute across double liaison dans une seule étape (concerted, syn)",
      "he": "BH₃ מוסיף על פני כפול קשר ב יחיד שלב (מתואם, syn)",
      "hr": "BH₃ dodaje se across dvostruka veza u jedan korak (concerted, syn)",
      "hu": "BH₃ addicionálódik a kettős kötésen át egyetlen lépésben (koncertált, syn)",
      "id": "BH₃ bertambah melintasi ikatan rangkap dalam satu langkah (serentak, syn)",
      "it": "BH₃ si addiziona across doppio legame in un solo passaggio (concerted, syn)",
      "ja": "BH₃が一段階で二重結合に付加する(協奏的、syn)",
      "ko": "BH₃가 이중 결합에 단일 단계로 첨가됨(협동, syn)",
      "lv": "BH₃ pievienojas across dubultsaite iekš viens solis (concerted, syn)",
      "nb": "BH₃ adds across double binding in ett trinn (concerted, syn)",
      "nl": "BH₃ adds across double binding in één stap (concerted, syn)",
      "pl": "BH₃ dodaje sie across wiazanie podwojne w jeden krok (concerted, syn)",
      "pt-BR": "BH₃ adiciona-se across ligação dupla em uma única etapa (concerted, syn)",
      "pt-PT": "BH₃ adiciona-se across ligação dupla em uma única etapa (concerted, syn)",
      "ro": "BH₃ se adaugă across legătură dublă în un singur pas (concerted, syn)",
      "ru": "BH₃ присоединяется across двойная связь в одна стадия (concerted, syn)",
      "sk": "BH₃ pridava sa across dvojita vazba v jeden krok (concerted, syn)",
      "sl": "BH₃ se doda across dvojna vez v en korak (concerted, syn)",
      "sv": "BH₃ adds across double bindning in ett steg (concerted, syn)",
      "th": "BH₃ เติมข้ามพันธะคู่ในขั้นเดียว (เกิดพร้อมกัน, syn)",
      "tr": "BH₃ eklenir çift bağ boyunca tek bolarakamakta (tek bolarakamaklı, syn)",
      "uk": "BH₃ приєднується across подвійний звʼязок у один крок (concerted, syn)",
      "vi": "BH₃ cộng qua liên kết đôi trong một bước (đồng thời, syn)",
      "zh-Hans": "BH₃ 以单一步骤跨双键加成(协同,syn)",
      "zh": "BH₃ 以单一步骤跨双键加成(协同,syn)"
    }
  },
  {
    "smiles": "CCCO",
    "description": {
      "en": "H₂O₂/OH⁻ replaces B with OH (retention of configuration)",
      "ar": "H₂O₂/OH⁻ يستبدل B مع OH (احتفاظ من تشكيل)",
      "cs": "H₂O₂/OH⁻ replaces B s OH (retention z konfigurace)",
      "da": "H₂O₂/OH⁻ replaces B med OH (retention of konfiguration)",
      "de": "H₂O₂/OH⁻ replaces B mit OH (Retention of Konfiguration)",
      "el": "H₂O₂/OH⁻...
Stereochemistry
{
  "en": "Syn addition (H and OH end up on same face)",
  "ar": "syn إضافة (H و OH ينتهي  على الوجه نفسه)",
  "cs": "Syn adice (H a OH end up na stejne strany)",
  "da": "syn-addition (H og OH end up on same face)",
  "de": "Syn-Addition (H und OH end up on same face)",
  "el": "Syn προσθήκη (H και OH καταλήγουν στην ίδια πλευρά)",
  "es-419": "Syn adición (H y OH end up on misma cara)",
  "es-ES": "Syn adición (H y OH end up on misma cara)",
  "es": "Syn adición (H y OH end up on misma cara)",
  "fi": "syn-additio (H ja OH end up on same face)",
  "fr": "Syn addition (H et OH end up on même face)",
  "he": "syn סיפוח (H ו OH מסתיים  על אותו פנים)",
  "hr": "Syn adicija (H i OH end up na iste strane)",
  "hu": "Syn addíció (H és OH ugyanarra az oldalra kerül)",
  "id": "Adisi syn (H dan OH berakhir pada sisi yang sama)",
  "it": "Syn addizione (H e OH end up on stessa faccia)",
  "ja": "syn付加(HとOHが同じ面に入る)",
  "ko": "syn 첨가(H와 OH가 같은 면에 놓임)",
  "lv": "Syn pievienosana (H un OH end up uz tas pasas puses)",
  "nb": "syn-addisjon (H og OH end up on same face)",
  "nl": "syn-additie (H en OH end up on same face)",
  "pl": "Syn addycja (H i OH end up na tej samej strony)",
  "pt-BR": "Syn adição (H e OH end up on mesma face)",
  "pt-PT": "Syn adição (H e OH end up on mesma face)",
  "ro": "Syn adiție (H și OH end up on aceeași față)",
  "ru": "Syn присоединение (H и OH end up на той же стороны)",
  "sk": "Syn adicia (H a OH end up na tej istej strany)",
  "sl": "Syn adicija (H v OH end up na iste strani)",
  "sv": "syn-addition (H och OH end up on same face)",
  "th": "การเติมแบบ syn (H และ OH ไปอยู่ด้านเดียวกัน)",
  "tr": "Syn kdeılma (H ve OH aynı yüzde oluşur)",
  "uk": "Syn приєднання (H і OH end up на того самого боку)",
  "vi": "Cộng syn (H và OH nằm cùng một mặt)",
  "zh-Hans": "syn 加成(H 和 OH 最终在同一面)",
  "zh": "syn 加成(H 和 OH 最终在同一面)"
}
Regiochemistry
{
  "en": "Anti-Markovnikov: OH ends up on less substituted carbon",
  "ar": "Anti-ماركوفنيكوف: OH ينتهي  على أقل مستبدل كربون",
  "cs": "Anti-Markovnikov: OH ends up na mene substituovany uhlik",
  "da": "Anti-Markovnikov: OH ends up on mindre substitueret kulstof",
  "de": "Anti-Markovnikov: OH ends up on weniger substituiert Kohlenstoff",
  "el": "αντι-Markovnikov: το OH καταλήγει στον λιγότερο υποκατεστημένο άνθρακα",
  "es-419": "Anti-Markovnikov: OH ends up on carbonoo menos sustituido",
  "es-ES": "Anti-Markovnikov: OH ends up on carbonoo menos sustituido",
  "es": "Anti-Markovnikov: OH ends up on carbonoo menos sustituido",
  "fi": "Anti-Markovnikov: OH ends up on vähemmän substituoitu hiili",
  "fr": "Anti-Markovnikov: OH ends up on carbonee le moins substitué",
  "he": "Anti-מרקובניקוב: OH מסתיים  על פחות מותמר פחמן",
  "hr": "Anti-Markovnikov: OH ends up na manje supstituiran ugljik",
  "hu": "anti-Markovnyikov: az OH a kevésbé szubsztituált szénre kerül",
  "id": "Anti-Markovnikov: OH berakhir pada karbon yang kurang tersubstitusi",
  "it": "Anti-Markovnikov: OH ends up on carbonioio meno sostituito",
  "ja": "anti-Markovnikov: OHはより低置換の炭素に入る",
  "ko": "anti-Markovnikov: OH가 덜 치환된 탄소에 놓임",
  "lv": "Anti-Markovnikov: OH ends up uz mazak aizvietots ogleklis",
  "nb": "Anti-Markovnikov: OH ends up on mindre substituert karbon",
  "nl": "Anti-Markovnikov: OH ends up on minder gesubstitueerd koolstof",
  "pl": "Anti-Markovnikov: OH ends up na mniej podstawiony wegiel",
  "pt-BR": "Anti-Markovnikov: OH ends up on carbonoo menos substituído",
  "pt-PT": "Anti-Markovnikov: OH ends up on carbonoo menos substituído",
  "ro": "Anti-Markovnikov: OH ends up on carbon mai puțîn substituit",
  "ru": "Anti-Markovnikov: OH ends up на менее замещенный углерод",
  "sk": "Anti-Markovnikov: OH ends up na menej substituovany uhlik",
  "sl": "Anti-Markovnikov: OH ends up na manj substituiran ogljik",
  "sv": "Anti-Markovnikov: OH ends up on mindre substituerad kol",
  "th": "Anti-Markovnikov: OH ไปอยู่บนคาร์บอนที่ถูกแทนที่น้อยกว่า",
  "tr": "anti-Markovnikov: OH daha az sübstitüe karbağa oluşur",
  "uk": "Anti-Markovnikov: OH ends up на менш заміщений вуглець",
  "vi": "Anti-Markovnikov: OH nằm trên carbon ít thế hơn",
  "zh-Hans": "Anti-Markovnikov:OH 最终在低取代碳上",
  "zh": "Anti-Markovnikov:OH 最终在低取代碳上"
}
Tips
[
  {
    "en": "No carbocation = no rearrangement",
    "ar": "لا كربوكاتيون = لا إعادة ترتيب",
    "cs": "Bez karbokation = bez presmyk",
    "da": "Intet carbokation = ingen omlejring",
    "de": "Kein Carbokation = keine Umlagerung",
    "el": "Χωρίς καρβοκατιόν = χωρίς αναδιάταξη",
    "es-419": "No carbocatión = sin reordenamiento",
    "es-ES": "No carbocatión = sin reordenamiento",
    "es": "No carbocatión = sin reordenamiento",
    "fi": "Ei karbokationia = ei uudelleenjärjestymistä",
    "fr": "No carbocation = pas de réarrangement",
    "he": "אין קרבוקציון = אין סידור מחדש",
    "hr": "Bez karbokation = bez pregrađivanje",
    "hu": "Nbancs karboknálion = nbancs átrendeződés",
    "id": "Tidak ada karbokation = tidak ada penataan ulang",
    "it": "No carbocatione = nessun riarrangiamento",
    "ja": "カルボカチオンなし = 転位なし",
    "ko": "탄소양이온이 없어 재배열이 없음",
    "lv": "Nav karbokations = nav pargrupesanas",
    "nb": "Ingen karbokation = ingen omleiring",
    "nl": "Geen carbokation = geen omlegging",
    "pl": "Brak karbokation = brak przegrupowanie",
    "pt-BR": "No carbocátion = sem rearranjo",
    "pt-PT": "No carbocátion = sem rearranjo",
    "ro": "No carbocation = fără rearanjare",
    "ru": "Нет карбокатион = нет перегруппировка",
    "sk": "Bez karbokation = bez prestavba",
    "sl": "Brez karbokation = brez preureditev",
    "sv": "Ingen karbokatjon = ingen omarrangering",
    "th": "ไม่มีคาร์โบแคตไอออน = ไม่มีการจัดเรียงใหม่",
    "tr": "Karbokdeyüzerinde yok = yeniden düzenlenme yok",
    "uk": "Немає карбокатіон = немає перегрупування",
    "vi": "Không có carbocation = không tái sắp xếp",
    "zh-Hans": "无碳正离子 = 无重排",
    "zh": "无碳正离子 = 无重排"
  },
  {
    "en": "B adds to less hindered (less substituted) carbon",
    "ar": "B يضيف إلى أقل معاق (أقل مستبدل) كربون",
    "cs": "B pridava se na mene hindered (mene substituovany) uhlik",
    "da": "B adds til mindre hindered (mindre substitueret) kulstof",
    "de": "B adds zu weniger hindered (weniger substituiert) Kohlenstoff",
    "el": "Το B προστίθεται στον λιγότερο παρεμποδισμένο (λιγότερο υποκατεστημένο) άνθρακα",
    "es-419": "B se añade a menos impedido (menos substituted) carbono",
    "es-ES": "B se añade a menos impedido (menos substituted) carbono",
    "es": "B se añade a menos impedido (menos substituted) carbono",
    "fi": "B adds kohti vähemmän hindered (vähemmän substituoitu) hiili",
    "fr": "B s'ajoute en moins encombré (moins substituted) carbone",
    "he": "B מוסיף ל פחות מופרע (פחות מותמר) פחמן",
    "hr": "B dodaje se u manje hindered (manje supstituiran) ugljik",
    "hu": "A B a kevésbé gátolt (kevésbé szubsztituált) szénhez addicionálódik",
    "id": "B bertambah ke karbon yang kurang terhalang (kurang tersubstitusi)",
    "it": "B si addiziona a meno ingombrato (meno substituted) carbonio",
    "ja": "Bはより立体障害の小さい(より低置換の)炭素に付加する",
    "ko": "B는 덜 혼잡한(덜 치환된) 탄소에 첨가됨",
    "lv": "B pievienojas uz mazak hindered (mazak aizvietots) ogleklis",
    "nb": "B adds til mindre hindered (mindre substituert) karbon",
    "nl": "B adds tot minder hindered (minder gesubstitueerd) koolstof",
    "pl": "B dodaje sie do mniej hindered (mniej podstawiony) wegiel",
    "pt-BR": "B adiciona-se a menos impedido (menos substituted) carbono",
    "pt-PT": "B adiciona-se a menos impedido (menos substituted) carbono",
    "ro": "B se adaugă la mai puțîn împiedicat (mai puțîn substituted) carbon",
    "ru": "B присоединяется в менее hindered (менее замещенный) углерод",
    "sk": "B pridava sa na menej hindered (menej substituovany) uhlik",
    "sl": "B se doda v manj hindered (manj substituiran) ogljik",
    "sv": "B adds till mindre hindered (mindre substituerad) kol",
    "th": "B เติมเข้าคาร์บอนที่กีดขวางน้อยกว่า (ถูกแทนที่น้อยกว่า)",
    "tr": "B daha az engellenmiş (daha az sübstitüe) karbüzerindea eklenir",
    "uk": "B приєднується до менш hindered (менш заміщений) вуглець",
    "vi": "B cộng vào carbon ít cản trở hơn (ít thế hơn)",
    "zh-Hans":...
Related Reactions

hydrohalogenation, oxymercuration

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