1. (a) Formulate four(4) different ways to synthesize 3-methylhexane from any readily available starting material. For each of these, show the reagent(s) required for each transformation, including all intermediates. (b) H.C. Brown used ester (2A) to test a new reducing agent which did indeed form alcohol (2B). How might he have made the ester (2A) from benzene. 2A C2Me NaBH4 AICI 3 CI 2B CH₂OH (c) Suggest synthesis for the target molecules (3A) and (3B) needed as intermediates. TM (3A) in the synthesis of brominated hydroxybenzoic acids and TM (3B) in the synthesis of model compounds for studying biological mechanisms of ester hydrolysis. OH CO₂ CHO O₂N Br

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1. (a) Formulate four(4) different ways to synthesize 3-methylhexane from any
readily available starting material. For each of these, show the reagent(s) required
for each transformation, including all intermediates.
(b) H.C. Brown used ester (2A) to test a new reducing agent which did indeed
form alcohol (2B). How might he have made the ester (2A) from benzene.
2A
C2Me
NaBH4
AICI 3
CI
2B
CH₂OH
(c) Suggest synthesis for the target molecules (3A) and (3B) needed as intermediates.
TM (3A) in the synthesis of brominated hydroxybenzoic acids and TM (3B) in the
synthesis of model compounds for studying biological mechanisms of ester
hydrolysis.
OH
CO₂
CHO
O₂N
Br
Transcribed Image Text:1. (a) Formulate four(4) different ways to synthesize 3-methylhexane from any readily available starting material. For each of these, show the reagent(s) required for each transformation, including all intermediates. (b) H.C. Brown used ester (2A) to test a new reducing agent which did indeed form alcohol (2B). How might he have made the ester (2A) from benzene. 2A C2Me NaBH4 AICI 3 CI 2B CH₂OH (c) Suggest synthesis for the target molecules (3A) and (3B) needed as intermediates. TM (3A) in the synthesis of brominated hydroxybenzoic acids and TM (3B) in the synthesis of model compounds for studying biological mechanisms of ester hydrolysis. OH CO₂ CHO O₂N Br
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