Show how you would synthesize the following alcohols by adding Grignard reagents to ethylene oxide.

  1. 2-phenylethanol
  2. 4-methylpentan-1-ol

Short Answer

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a.

b.

c.

Step by step solution

01

Ethylene oxide with Grignard reagent

When ethylene oxide (oxirane) is treated with Grignard reagent (RMgX), it forms and then hydrolysis to form primary alcohol.Grignard reagents break the epoxide ring.

02

(a) Synthesis of alcohol

a.

When Grignard reagent (C6H5MgBr) is added to ethylene oxide, it forms C6H5-CH2-CH2-OMgBr and further hydrolysis to form primary alcohol (C6H5-CH2-CH2-OH). The dark bond describes a new C-C bond.

03

(b)  Synthesis of alcohol

b.When Grignard reagent (CH3-CH(CH3)-CH2MgCl) is added to ethylene oxide, it forms

CH3-CH(CH3)-CH2CH2-CH2-OMgCl and further hydrolysis to form primary alcohol

(CH3-CH(CH3)-CH2-CH2-CH2-OH ). The dark bond describes a new C-C bond.

04

(c) Synthesis of alcohol

c. When Grignard reagent (RMgI) is added to ethylene oxide, it forms RCH2-CH2-OMgI and further hydrolysis to form primary alcohol (RCH2-CH2-OH). The dark bond describes a new C-C bond.

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Geminal diols, or 1,1-diols, are usually unstable, spontaneously losing water to give carbonyl compounds. Therefore, germinal diols are regarded as hydrated forms of ketones and aldehydes. Propose a mechanism for the acid-catalyzed loss of water from propane-2,2-diol to give acetone.

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