Devise the most efficient synthesis for the carboxylic acid below using a starting material and reagents from the tables. Give y rst step. he answer 4fh means treat t-butanol(4) with conc. HCl(f) then treat the product with KOH in alcohol(h). Starting materials Br OH OH Reagents a Mg/dry ether H3C OH 2 Br 6 Br 7 3 LOH OH OH H 8 e Aqueous H2SO4 at reflux 1 KMnO4/H3O b 1. CO₂ 2. acidic workup f Conc. HCI or HCI (gas) j Na₂ CrO4/ aqueous H₂SO c NaCN/THF or DMF g PBг3 k 1. BH3/THF 2. H₂O₂/aq. NaOH d NaCN/dil. aqueous H2SO4 h KOH/alcohol

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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
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
Br
OH
OH
HO
H3C
OH
2
Br
6
Reagents
a Mg / dry ether
Br
7
3
OH
4
OH
e Aqueous H2SO4 at reflux
b 1. CO₂ 2. acidic workup
f Conc. HCI or HCI (gas)
c NaCN/THF or DMF
g PBг3
d NaCN/dil. aqueous H2SO4
h KOH/alcohol
-OH
8
50
H
| KMnO4 / H₂O*
J Na₂ CгO / aqueous H₂SO
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 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 Br OH OH HO H3C OH 2 Br 6 Reagents a Mg / dry ether Br 7 3 OH 4 OH e Aqueous H2SO4 at reflux b 1. CO₂ 2. acidic workup f Conc. HCI or HCI (gas) c NaCN/THF or DMF g PBг3 d NaCN/dil. aqueous H2SO4 h KOH/alcohol -OH 8 50 H | KMnO4 / H₂O* J Na₂ CгO / aqueous H₂SO k 1. BH3/THF 2. H₂O₂/aq. NaOH
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