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Chapter 16: Q20P (page 753)

What alcohols are obtained from the Reduction of the following compounds with sodium borohydride?

a. 2-methylpropanal b. cyclohexanone c. 4-tert-butylcyclohexanone d. acetophenone

Short Answer

Expert verified

On reduction, aldehyde gives primary alcohol.

  1. 2-methylproponal on reduction in the presence of sodium borohydride converted into 2- methylpropanol.

Reduction of 2-methyl propanol (a)

Step by step solution

01

Reduction of aldehydes

On reduction, aldehyde gives primary alcohol.

  1. 2-methylproponal on reduction in the presence of sodium borohydride converted into 2- methylpropanol.

Reduction of 2-methyl propanol (a)

02

Reduction of ketone

On reduction, ketone gives secondary alcohol.

b. Cyclohexanone on reduction gives cyclohexanol.


Reduction of cyclohexanone (b)

c . 4-tert-butylcyclohexanone on reduction gives 4-tert-butylcyclohexanol.


Reduction of 4-tert-butylcyclohexanone (c)

d. Acetophenone on reduction, gives tertiary alcohol (2-acetophenol).


Reduction of acetophenone (d)

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Most popular questions from this chapter

a. Show how the following compounds can be prepared, using ethyne as one of the starting materials:

  1. 1-pentyn-3-ol
  2. 1-phenyl-2-butyn-1-ol
  3. 2-methyl-3-hexyn-2-ol

b. Explain why ethyne should be alkylated before, rather than after, nucelophilic addition.

Draw the structure for each of the following:

a. isobutyraldehyde

b. 4-hexenal

c. diisopentyl ketone

d. 3-methylcyclohexanone

e. 2,4-pentanedione

f. 4-bromo-3-heptanone

g. γ-bromocaproaldehyde

h. 2-ethylcyclopentanecarbaldehyde

i. 4-methyl-5-oxohexanal

Hydration of an aldehyde is also catalyzed by hydroxide ion. Propose a mechanism for the reaction.

Question: Draw the structure for each of the following:

a.

b.

c.

d.

Which of the following are

a. hemiacetals?

b. acetals?

c. hydrates?
See all solutions

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