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Chapter 25: PROBLEM 25.13 (page 1012)

Question: Draw the product of each reaction.

a.

b.

c.

d.

Short Answer

Expert verified

Answer

a.

b.

c.


d.

Step by step solution

01

Reduction of aldehyde to imine

The aldehyde is reduced to imine when the amine attacks the carbonyl carbon. The lone pair of electrons moves from the amine group to the electron-deficient group of C=O.

02

Reduction of imine to amine

The reduction of imine to amine is completed in the presence of reducing agents, such as lithium aluminum hydride, sodium cyanoborohydride, etc. The reducing agents produce hydride in the deficient groups.

03

Explanation

a. The given aldehyde compound is reduced to amine, as shown below.

Reduction of aldehyde

b. The given ketone compound is reduced to amine, as shown below.

Reduction of aldehyde

c.

Reduction of aldehyde

d. The given ketone compound is reduced to amine, as shown below.

Reduction of aldehyde

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Most popular questions from this chapter

Question: Which compound in each pair is more basic:

a. CH32NHandNH3

b. CH3CH2NH2andClCH2CH2NH2 ?

Devise a synthesis of each compound from benzene, any organic alcohols having four carbons or fewer, and any required reagents.

a

b

c

Question: a. Explain why phentermine phCH2CCH32NH2 can't be made by a reductive amination reaction.

b. Give a systematic name for phentermine, one of the components of the banned diet drug fen鈥損hen.

Question: Draw the structure that corresponds to each name.

  1. N-isobutylcyclopentanamine
  2. tri-tert-butylamine
  3. N, N-diisopropylaniline
  4. N-methyl pyrrole
  5. N-methylcyclopentanamine
  6. 3-methylhexan-2-amine
  7. 2-sec-butylpiperidine
  8. (S)-heptan-2-amine

Answer the following questions about benzphetamine, a habit-forming diet pill sold under the trade name Didrex

  1. Label the stereogenic center(s).
  2. What amide(s) can be reduced to form benzphetamine?
  3. What carbonyl compound and amine can be used to make benzphetamine by reductive amination? Draw all possible methods.
  4. What products are formed by Hofmann elimination from benzphetamine? Label the major product.
See all solutions

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