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). Starting materials Br Reagents 1 OH a Mg/ dry ether OH H₂C b 1. CO₂ 2. acidic workup c NaCN/ THF or DMF d NaCN/dil. aqueous H₂SO4 The most efficient synthetic route is e Aqueous H₂SO4 at reflux f Conc. HCI or HCI (gas) g PBr₂ h KOH/alcohol HO+ 4 i KMnO4/H₂O¹ j Na₂ CrO4! aqueous H₂SO4 k 1. BH THF 2. H₂O₂/aq. NaOH Previous Next>

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter19: Aldehydes And Ketones: Nucleophilic Addition Reactions
Section19.SE: Something Extra
Problem 39MP
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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. HCI(f) then treat the product with KOH in alcohol(h).
Starting materials
Br
Reagents
OH
a Mg/ dry ether
OH
H₂C
b 1. CO₂ 2. acidic workup
c NaCN/ THF or DMF
d NaCN/dil. aqueous H₂SO4
The most efficient synthetic route is
e Aqueous H₂SO4 at reflux
f Conc. HCI or HCI (gas)
g PBr₂
h KOH/alcohol
HO+
4
i KMnO4 / H₂O¹
j Na₂ CrO4! aqueous H₂SO4
K 1.BH/THF 2. H₂O₂/aq. NaOH
Previous
Next>
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. HCI(f) then treat the product with KOH in alcohol(h). Starting materials Br Reagents OH a Mg/ dry ether OH H₂C b 1. CO₂ 2. acidic workup c NaCN/ THF or DMF d NaCN/dil. aqueous H₂SO4 The most efficient synthetic route is e Aqueous H₂SO4 at reflux f Conc. HCI or HCI (gas) g PBr₂ h KOH/alcohol HO+ 4 i KMnO4 / H₂O¹ j Na₂ CrO4! aqueous H₂SO4 K 1.BH/THF 2. H₂O₂/aq. NaOH Previous Next>
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