Mechanism for the Dehydration of Alcohol into Alkene

Different types of alcohols may dehydrate through a slightly different mechanism pathway. However, the general idea behind each dehydration reaction is that the –OH group in the alcohol donates two electrons to H⁺ from the acid reagent, forming an alkyloxonium ion. This ion acts as a very good leaving group which leaves to form a carbocation. The deprotonated acid (the nucleophile) then attacks the hydrogen adjacent to the carbocation and form a double bond.

Primary alcohols undergo bimolecular elimination (E2 mechanism) while secondary and tertiary alcohols undergo unimolecular elimination (E1 mechanism). The relative reactivity of alcohols in dehydration reaction is ranked as the following

Methanol < primary < secondary < tertiary

Primary alcohol dehydrates through the E2 mechanism. Oxygen donates two electrons to a proton from sulfuric acid H₂SO₄, forming an alkyloxonium ion. Then the nucleophile HSO₄^– back-side attacks one adjacent hydrogen and the alkyloxonium ion leaves in a concerted process, making a double bond.

Secondary and tertiary alcohols dehydrate through the E1 mechanism. Similarly to the reaction above, secondary and tertiary –OH protonate to form alkyloxonium ions. However, in this case the ion leaves first and forms a carbocation as the reaction intermediate. The water molecule (which is a stronger base than the HSO_4^- ion) then abstracts a proton from an adjacent carbon, forming a double bond. Notice in the mechanism below that the aleke formed depends on which proton is abstracted: the red arrows show formation of the more substituted 2-butene, while the blue arrows show formation of the less substituted 1-butene. Recall the general rule that more substituted alkenes are more stable than less substituted alkenes, and trans alkenes are more stable than cis alkenes. Thereore, the trans diastereomer of the 2-butene product is most abundant.

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طبيبة أسنان تحذر.. لا تتجاهل هذه العلامة بعد التنظيف

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الآخبار التكنلوجية

أداء خلايا البيروفسكايت الشمسية تحت الماء قد يزيد كفاءة تحويل الكهرباء

مسافة الأمان: أساس القيادة الآمنة وتجنب الحوادث

هل القيادة السريعة تعني استهلاك اكثر للوقود؟

لماذا يعتبر كوكب المريخ غير صالح للحياة؟

المزيد

مواضيع ذات صلة

E-selective reduction of alkynes using sodium in liquid ammonia

Amine synthesis using functional group interconversions

Functional group interconversion

Multiple step syntheses: avoid chemoselectivity problems

Synthons are idealized reagents

The E-selective Wittig reaction

The Z-selective Wittig reaction

Stereoselectivity in the Wittig reaction depends on the ylid

The Peterson reaction is stereospecific

The one-step Julia olefination

The Julia olefi nation is stereoselective

The Julia olefination is regiospecific and connective