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Show how you would accomplish the following

Chapter 13, Problem 30P

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QUESTION:

Show how you would accomplish the following synthetic conversions.

(a) benzyl bromide  benzylamine

(b) 1-bromo-2-phenylethane  3-phenylpropan-1-amine

(c) pentanoic acid  pentan-1-amine

(d) pentanoic acid  hexan-1-amine

(e) (R)-2-bromobutane  (S)-butan-2-amine

(f) (R)-2-bromobutane  (S)-2-methylbutan-1-amine

(g) hexan-2-one  1-amino-2-methylhexan-2-ol

Questions & Answers

QUESTION:

Show how you would accomplish the following synthetic conversions.

(a) benzyl bromide  benzylamine

(b) 1-bromo-2-phenylethane  3-phenylpropan-1-amine

(c) pentanoic acid  pentan-1-amine

(d) pentanoic acid  hexan-1-amine

(e) (R)-2-bromobutane  (S)-butan-2-amine

(f) (R)-2-bromobutane  (S)-2-methylbutan-1-amine

(g) hexan-2-one  1-amino-2-methylhexan-2-ol

ANSWER:

Solution 30P

(a)

Treatment of benzyl bromide with sodium azide gives (azidomethyl)benzene.

Lithium aluminum hydride is used as a reducing agent for the conversion of azide to amine. So, (azidomethyl)benzene is reacted with lithium aluminum hydride followed by the hydrolysis gives the desired product.

(b)

Treatment of 1-bromo-2-phenylethane with cyanide ion gives 3-phenylpropanenitrile.

Now, 3-phenylpropanenitrile is reacted with  in the presence of nickel catalyst gives the desired product.

(c)

Treatment of pentanoic with thionyl chloride gives pentanoyl chloride.

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