Solution Found!
Show how you would accomplish the following
Chapter 13, Problem 30P(choose chapter or problem)
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.