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). Lion Starting materials Br Reagents a Mg/ dry ether H₂C OH b 1. CO₂ 2. acidic workup c NaCN/THF or DMF 2 d NaCN/dil. aqueous H₂SO4 Br Br 7 OH e Aqueous H₂SO4 at reflux f Conc. HCI or HCI (gas) g PBr3 h KOH/alcohol Hot 4 8 i KMnO4/H3O* j Na₂ CrO4/ aqueous H₂SO4 k 1. BH3/THF 2. H₂O₂/aq. NaOH I

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Chapter1: Chemical Foundations
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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
Br
Reagents
1
OH
a Mg/ dry ether
b 1. CO₂
H3C
OH
6
2. acidic workup
c NaCN/THF or DMF
2
d NaCN/dil. aqueous H₂SO4
Br
Br
7
3
g PBr3
OH
OH
e Aqueous H₂SO4 at reflux
f Conc. HCI or HCI (gas)
h KOH/alcohol
Hot
4
8
i KMnO4 / H3O+
5
H
j Na₂ CrO4 / aqueous H₂SO4
. Å
k 1. BH3/THF 2. H₂O₂/aq. NaOH
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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 Br Reagents 1 OH a Mg/ dry ether b 1. CO₂ H3C OH 6 2. acidic workup c NaCN/THF or DMF 2 d NaCN/dil. aqueous H₂SO4 Br Br 7 3 g PBr3 OH OH e Aqueous H₂SO4 at reflux f Conc. HCI or HCI (gas) h KOH/alcohol Hot 4 8 i KMnO4 / H3O+ 5 H j Na₂ CrO4 / aqueous H₂SO4 . Å k 1. BH3/THF 2. H₂O₂/aq. NaOH Previous Next
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