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

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter19: Enolate Anions And Enamines
Section: Chapter Questions
Problem 19.57P
icon
Related questions
icon
Concept explainers
Question
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
Expert Solution
steps

Step by step

Solved in 3 steps with 1 images

Blurred answer
Knowledge Booster
Catalysis and Enzymatic Reactions
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
  • SEE MORE QUESTIONS
Recommended textbooks for you
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9781305580350
Author:
William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:
Cengage Learning
Organic Chemistry: A Guided Inquiry
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:
9780618974122
Author:
Andrei Straumanis
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9781305080485
Author:
John E. McMurry
Publisher:
Cengage Learning