Starting materials Br Reagents HO. 1 34. a Mg / dry ether H₂C 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 Br 7 OH _OH e Aqueous H₂SO4 at reflux g PBr3 f Conc. HCI or HCI (gas) h KOH / alcohol Hot 8 wit H i KMnO4 / H3O+ 5 j Na₂ CrO4/ aqueous H₂SO4 k 1. BH3/THF 2. H₂O₂/aq. NaOH i Å I

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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
HO.
1
34.
a Mg / dry ether
H₂C
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
Br
7
OH
_OH
e Aqueous H₂SO4 at reflux
g PBr3
f Conc. HCI or HCI (gas)
h KOH / alcohol
Hot
8
wit
H
i KMnO4 / H3O+
5
j Na₂ CrO4/ aqueous H₂SO4
k 1. BH3/THF 2. H₂O₂/aq. NaOH
i Å
I
Transcribed Image Text:Starting materials Br Reagents HO. 1 34. a Mg / dry ether H₂C 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 Br 7 OH _OH e Aqueous H₂SO4 at reflux g PBr3 f Conc. HCI or HCI (gas) h KOH / alcohol Hot 8 wit H i KMnO4 / H3O+ 5 j Na₂ CrO4/ aqueous H₂SO4 k 1. BH3/THF 2. H₂O₂/aq. NaOH i Å I
Starting materials
Br
Reagents
OH
1
H3C
34.
a Mg/ dry ether
OH
b 1. CO₂ 2. acidic workup
c NaCN / THF or DMF
2
d NaCN/dil. aqueous H₂SO4
Br
The most efficient synthetic route is
Br
7
OH
LOH
e Aqueous H₂SO4 at reflux
g PBr3
f Conc. HCI or HCI (gas)
h KOH/alcohol
Hot
8
i KMnO4 / H3O+
5
H
j Na₂ CrO4 / aqueous H₂SO4
1 Å
k 1. BH₂/THF 2. H₂O₂/aq. NaOH
Transcribed Image Text:Starting materials Br Reagents OH 1 H3C 34. a Mg/ dry ether OH b 1. CO₂ 2. acidic workup c NaCN / THF or DMF 2 d NaCN/dil. aqueous H₂SO4 Br The most efficient synthetic route is Br 7 OH LOH e Aqueous H₂SO4 at reflux g PBr3 f Conc. HCI or HCI (gas) h KOH/alcohol Hot 8 i KMnO4 / H3O+ 5 H j Na₂ CrO4 / aqueous H₂SO4 1 Å k 1. BH₂/THF 2. H₂O₂/aq. NaOH
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