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 H₂C Key OH 7 Reagents Br a Mg/dry ether OH OH b 1. CO₂ 2. acidic workup c NaCN/THF or DMF d NaCN/dil. aqueous H₂SO The most efficient synthetic route is e Aqueous H₂SO, at reflux f Conc. HCI or HCI (gas) 9 PBr h KOH/alcohol HO+ 4 I KMnO₁/H₂O J Na₂ CrO₂ / aqueous H₂SO4 K 1.BHy/THF 2. H₂O₂/aq. NaOH

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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).
Starting materials
Reagents
1
Br
a Mg/dry ether
OH
6
H₂C
OH
c NaCN/THF or DMF
"225"
b 1. CO₂ 2. acidic workup
d NaCN/dil. aqueous H₂SO4
The most efficient synthetic route is
Br
Br
7
3
g PBr3
OH
OH
e Aqueous H₂SO4 at reflux
f Conc. HCI or HCI (gas)
h KOH/alcohol
Hot
8
i KMnO4/H₂O*
5
H
j Na₂ CrO₂ / aqueous H₂SO4
k 1. BH3/THF 2. H₂O₂/aq. NaOH
TÅ
요
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). Starting materials Reagents 1 Br a Mg/dry ether OH 6 H₂C OH c NaCN/THF or DMF "225" b 1. CO₂ 2. acidic workup d NaCN/dil. aqueous H₂SO4 The most efficient synthetic route is Br Br 7 3 g PBr3 OH OH e Aqueous H₂SO4 at reflux f Conc. HCI or HCI (gas) h KOH/alcohol Hot 8 i KMnO4/H₂O* 5 H j Na₂ CrO₂ / aqueous H₂SO4 k 1. BH3/THF 2. H₂O₂/aq. NaOH TÅ 요
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