How would you synthesize the following compounds from benzene using reagents from the table? a b с d CH3CI / AICI 3 CH3CI Cl₂/FeCl3 NaCN a) m-Chlorobenzoic acid f g h Reagents 1. NaOH / H₂O 2. H3O+ NBS/(PhCO2)2 1. CO₂ 2. H3O+ KMnO4 / H3O+ b) p-Methylbenzoic acid (p-toluic acid) i j k I Cl₂ Br₂ / FeBr3 HNO3 / H₂SO4 Mg / dry ether

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter9: Addition Via Cyclic Intermediate
Section: Chapter Questions
Problem 2E
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How would you synthesize the following compounds from butanoic acid using reagents from the table?
Use letters from the table to list reagents in the order used (first at the left).
Example: ab
a
b
с
1. NaBH4
2. H3O+
1. LIAIH4
2. H3O*
H₂/Pt
1. BH3/THF
2. H₂O₂/NaOH
a) 1-butanol
b) 2-methylbutanoic acid
e
f
g
h
i
Reagents
PBr3
Mg / dry ether
1. Li 2. Cul
1-bromobutane
H3O*, heat
j
k
m
n
KOH / alcohol
KOtBu
1. CO₂ 2. H3O+
HBr, dark
no peroxides
NaCN
Transcribed Image Text:How would you synthesize the following compounds from butanoic acid using reagents from the table? Use letters from the table to list reagents in the order used (first at the left). Example: ab a b с 1. NaBH4 2. H3O+ 1. LIAIH4 2. H3O* H₂/Pt 1. BH3/THF 2. H₂O₂/NaOH a) 1-butanol b) 2-methylbutanoic acid e f g h i Reagents PBr3 Mg / dry ether 1. Li 2. Cul 1-bromobutane H3O*, heat j k m n KOH / alcohol KOtBu 1. CO₂ 2. H3O+ HBr, dark no peroxides NaCN
How would you synthesize the following compounds from benzene using reagents from the table?
a
b
с
d
CH3CI / AICI 3
CH3CI
Cl₂/FeCl3
NaCN
a) m-Chlorobenzoic acid
f
g
h
Reagents
1. NaOH / H₂O
2. H3O+
NBS/(PhCO2)2
1. CO₂ 2. H3O+
KMnO4 / H3O+
b) p-Methylbenzoic acid (p-toluic acid)
i
j
k
I
Cl₂
Br₂ / FeBr3
HNO3 / H₂SO4
Mg / dry ether
Transcribed Image Text:How would you synthesize the following compounds from benzene using reagents from the table? a b с d CH3CI / AICI 3 CH3CI Cl₂/FeCl3 NaCN a) m-Chlorobenzoic acid f g h Reagents 1. NaOH / H₂O 2. H3O+ NBS/(PhCO2)2 1. CO₂ 2. H3O+ KMnO4 / H3O+ b) p-Methylbenzoic acid (p-toluic acid) i j k I Cl₂ Br₂ / FeBr3 HNO3 / H₂SO4 Mg / dry ether
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