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Chapter 10: Q43P (page 537)

Suggest carbonyl compounds and reducing agents that might be used to form the following alcohols.

  1. heptan-1-ol
  2. 1-cyclohexylethanol
  3. 1-phenylpropan-1-ol

e)

f)

Short Answer

Expert verified

a)

b)

c)

d)

e)

f)

Step by step solution

01

Reducing agents

Reducing agents are used for reducing the organic compounds containing carbonyl compounds like aldehydes, ketones, esters etc. There are different reducing agents like NaBH4 , LiAIH4used for reducing carbonyl-containing compounds.

02

 Step 2: Formation of heptan-1-ol

a) When aldehyde is treated with a reducing agent in methanol, the carbonyl group is reduced to alcohol and forms heptan-1-ol.

Formation of heptan-1-ol

03

Formation of 1-cyclohexylethanol

b) When ketone is treated with a reducing agent in methanol or followed by hydrolysis, then the carbonyl group is reduced to alcohol and forms 1-cyclohexylethanol.

Formation of 1-cyclohexylethanol

04

Formation of 1-phenylpropan-1-ol

c) When ketone is treated with a reducing agent in methanol or followed by hydrolysis, then the carbonyl group is reduced to alcohol and forms 1-phenylpropan-1-ol.


Formation of 1-phenylpropan-1-ol

05

Formation of alcohol

d) When ketone is treated with a reducing agent in methanol or followed by hydrolysis, then the carbonyl group is reduced to an alcohol.


Formation of alcohol

06

Formation of alcohol

e) When ketone and the aldehyde-containing compound is treated with a reducing agent NabH4 in methanol or LiAIH4followed by hydrolysis, then both the carbonyl groups of ketone and aldehyde are reduced to an alcohol.

Formation of alcohol

07

 Step 7: Formation of alcohol

f) When ketone and the ester-containing compound is treated with a reducing agent in methanol, then only the carbonyl group of the ketone is reduced to an alcohol.

Formation of alcohol

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Most popular questions from this chapter

Show how you would synthesize the following compounds from alkyl halides, vinyl halides, and aryl halides containing no more than six carbon atoms.

  1. octane
  2. vinylcyclohexane
  3. trans-oct-3-ene
  4. cyclopentyl propyl ketone

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.

Compound A (C7H11Br) is treated with magnesium in ether to give B (C7H11MgBr) , which reacts violently with D2O to give 1-methylcyclohexene with a deuterium atom on the methyl group (C). Reaction of B with acetone (CH3COCH3) followed by hydrolysis gives D(C10H18O). Heating D with concentrated H2SO4 gives E (C10H16) , which decolorizes two equivalents of Br2 to give F(C10H16Br4) . E undergoes hydrogenation with excess H2 and a Pt catalyst to give isobutylcyclohexane. Determine the structures of compounds A through F, and show your reasoning throughout.

Question: Predict the products of the following reactions.

(a)CH3CH2Br+Mg鈫�ether

(b) isobutyliodide+2Li鈫�hexane

(c) 1-bromo-4-fluorocyclohexane+Mg鈫�THF

(d) CH2=CCl-CH2CH3+2Li鈫�ether

Predict which member of each pair is more acidic, and explain the reasons for your predictions.

(a) cyclohexanol or 3-chlorophenol

(b) cyclopentanol or cyclopentanethiol

(c) cyclopentanol or cyclopentanecarboxylic acid

(d) pentan-1-ol or 2,2-dichloropentan-1-ol
See all solutions

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