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Magazine Chapter 10: Q19P (page 520)
Show how you would synthesize the following alcohols by adding Grignard reagents to ethylene oxide.
- 2-phenylethanol
- 4-methylpentan-1-ol
Short Answer
a.
b.
c.
Step by step solution
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.
(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.
(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.
(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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