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.
Chapter 10: Q19P (page 520)
Show how you would synthesize the following alcohols by adding Grignard reagents to ethylene oxide.
a.
b.
c.
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Get started for freeGeminal 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.
Devise a synthesis for each compound, starting with methylenecyclohexane and any other reagents you need.
(a) 1-methylcyclohexanol (b) cyclohexylmethanol
(c) 1-(hydroxymethyl)cyclohexanol (d) trans-2-methylcyclohexanol
(e) 2-chloro-1-methylcyclohexanol (f) 1-(phenylmethyl)cyclohexanol
Authentic skunk spray has become valuable for use in scent-masking products. Show how you would synthesize the two major components of skunk spray (3-methylbutane-1-thiol and but-2-ene-1-thiol) from any of the readily available butenes or from buta-1,3-diene.
Show how you would synthesize each tertiary alcohol by adding an appropriate Grignard reagent to a ketone.
(a)3-phenylhexane-3-ol (3ways)
(b) Ph3 COH
(c) 1-ethylcyclopentanol
(d) 2-cyclopentylpentan-2-ol
A formate ester, such as ethyl formate, reacts with an excess of a Grignard reagent to give (after protonation) secondary alcohols with two identical alkyl groups.
a. Propose a mechanism to show how the reaction of ethyl formate with an excess of allylmagnesium bromide gives, after protonation, hepta-1,6-dien-4-ol.
b. Show how you would use reactions of Grignard reagents with ethyl formate to synthesize the following secondary alcohols.
i. pentan-3-ol
ii. diphenylmethanol
iii. trans, trans-nona-2,7-dien-5-ol
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