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). HO. Starting materials Br ton OH H3C OH Br 7 Reagents a Mg / dry ether e Ethanol, H2SO4(trace) at reflux i OsO4 b 1. CO, 2. acidic workup f Conc, HCI į Naz Cro4 / aqueous H2SO, c NACN / THF or DMF g HBr к 1. Вн,THF 2. Н,ОJaq, NaOH d NaCN / dil. aqueous H2SO4 h KOH / alcohol

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter20: Carboxylic Acids And Nitriles
Section20.SE: Something Extra
Problem 26MP
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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).
HO,
Starting materials
Br
Br
ton
HO.
OH
H.
H3C
1
2
3
он
он
Br
7
Reagents
a Mg / dry ether
e Ethanol, H2SO4(trace) at reflux
i Os04
b 1. CO2 2. acidic workup
f Conc. HCI
į Naz Cro4 / aqueous H,SO4
c NACN / THF or DMF
9 HBr
k 1. BH3/THF 2. H2O2/aq. NAOH
d NaCN / dil. aqueous H2SO4
h КОН/alcohol
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). HO, Starting materials Br Br ton HO. OH H. H3C 1 2 3 он он Br 7 Reagents a Mg / dry ether e Ethanol, H2SO4(trace) at reflux i Os04 b 1. CO2 2. acidic workup f Conc. HCI į Naz Cro4 / aqueous H,SO4 c NACN / THF or DMF 9 HBr k 1. BH3/THF 2. H2O2/aq. NAOH d NaCN / dil. aqueous H2SO4 h КОН/alcohol
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