Devise the most efficient synthesis for the carboxylic acid below using a starting material and reagents from the tables. Give your route by specifying the number of the starting material followed by the letters of the reagents you would use beginning with the first step. The answer 4fh means treat t-butanol (4) with conc. HCI(f) then treat the product with KOH in alcohol(h).

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter24: Carboxylic Acids & Derivatives
Section: Chapter Questions
Problem 10E
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Devise the most efficient synthesis for the carboxylic acid below using a starting material and reagents from the tables. Give your route by specifying the number of the
starting material followed by the letters of the reagents you would use beginning with the first step.
The answer 4fh means treat t-butanol(4) with conc. HCl(f) then treat the product with KOH in alcohol(h).
CH3
Starting materials
Reagents
Br
OH
a Mg / dry ether
34
H3C
OH
6
b 1. CO₂ 2. acidic workup
c NaCN / THF or DMF
2
d NaCN/dil. aqueous H₂SO4
Br
The most efficient synthetic route is ab
Br
7
3
g HBr
f Conc. HCI
e Ethanol, H₂SO4(trace) at reflux
OH
OH
h KOH/alcohol
-OH
8
i OsO4
5
H
j Na₂ CrO4 / aqueous H₂SO4
1
K 1.BH3/THF 2. H₂O₂/aq. NaOH
Transcribed Image Text:Devise the most efficient synthesis for the carboxylic acid below using a starting material and reagents from the tables. Give your route by specifying the number of the starting material followed by the letters of the reagents you would use beginning with the first step. The answer 4fh means treat t-butanol(4) with conc. HCl(f) then treat the product with KOH in alcohol(h). CH3 Starting materials Reagents Br OH a Mg / dry ether 34 H3C OH 6 b 1. CO₂ 2. acidic workup c NaCN / THF or DMF 2 d NaCN/dil. aqueous H₂SO4 Br The most efficient synthetic route is ab Br 7 3 g HBr f Conc. HCI e Ethanol, H₂SO4(trace) at reflux OH OH h KOH/alcohol -OH 8 i OsO4 5 H j Na₂ CrO4 / aqueous H₂SO4 1 K 1.BH3/THF 2. H₂O₂/aq. NaOH
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