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 Reagents a Mg/dry ether H₂C b 1. CO₂ 2. acidic workup c NaCN/THF or DMF d NaCN/dil. aqueous H₂SO4 The most efficient synthetic route is e Ethanol, H₂SO4(trace) at reflux f Conc. HCI g HBr Hot h KOH/alcohol A i OsO₂ J Na₂ CrO₂ / aqueous H₂SO4 k 1. BHYTHF 2 H₂O₂/aq NaOH I Å

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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
Reagents
a Mg/dry ether
H₂C
OH
OH
b 1. CO₂ 2. acidic workup
c NaCN/THF or DMF
d NaCN/dil. aqueous H₂SO4
Br
The most efficient synthetic route is
3
f Conc. HCI
g HBr
OH
OH
e Ethanol, H₂SO4(trace) at reflux
h KOH/alcohol
Hot
i OsO₂
J Na₂ CrO₂ / aqueous H₂SO4
k 1. BHYTHF 2 H₂O₂/aq NaOH
. Å
I
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 Reagents a Mg/dry ether H₂C OH OH b 1. CO₂ 2. acidic workup c NaCN/THF or DMF d NaCN/dil. aqueous H₂SO4 Br The most efficient synthetic route is 3 f Conc. HCI g HBr OH OH e Ethanol, H₂SO4(trace) at reflux h KOH/alcohol Hot i OsO₂ J Na₂ CrO₂ / aqueous H₂SO4 k 1. BHYTHF 2 H₂O₂/aq NaOH . Å I
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