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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

Question: The only organic compound obtained when compound Z undergoes the following sequence of reactions gives the 1H NMR spectrum shown.

Identify compound Z.

The pKa of protonated acetone is about -7.5, and the pKa of protonated hydroxylamine is 6.0.

a. In a reaction with hydroxylamine at pH 4.5 (Figure 16.2), what fraction of acetone is present in its acidic, protonated form? (Hint: See Section 2.10.)

b. In a reaction with hydroxylamine at pH 1.5, what fraction of acetone is present in its acidic, protonated form?

c. In a reaction with acetone at pH 1.5 (Figure 16.2), what fraction of hydroxylamine is present in its reactive basic form?

Question: How many signals would the product of the following reaction show in

a.its 1H NMR spectrum?

b.its 13C NMR spectrum?

Show how the following compounds can be synthesized from cyclohexanol.

a.

b.

c.

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

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