A J C G B J SOCI2 → 1) 9-BBN 2) H₂O₂, NaOH A CH3OH A H₂ Pd/Lindlar's cat. 1) 9-BBN 2) H₂O2, NaOH 1) 03 2) Zn, H₂O B F D J KOH ethanol I 1) Hg(OAc)2, CH3OH 2) NaBH4, NaOH Br₂ H₂O PCC CH₂Cl₂ = C + J major F minor 요 CHCH + HCH CH3 C TSCI pyridine H + minor substitution products E A: B: C: D: E: F: G: H: 1: J:

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
Chapter21: Benzene And The Concept Of Aromaticity
Section: Chapter Questions
Problem 21.26P: Compound I (C11H14O2) is insoluble in water, aqueous acid, and aqueous NaHCO3, but dissolves readily...
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Supplemental Assignment 3: Road Map: From the following data provide structures A through J.
A
J
с
B
G
J
SOCI₂
1) 9-BBN
2) H₂O₂, NaOHA
CH3OH
A
H₂
Pd/Lindlar's cat.
1) 9-BBN
2) H₂O2, NaOH
B
1) 03
2) Zn, H₂O
D
J
KOH
ethanol
I
1) Hg(OAc)2, CH3OH
2) NaBH4, NaOH
Br₂
H₂O
0=
с + J + minor substitution products
major minor
PCC
CH₂Cl₂
|=
F
i
CH3CHCH + HCH
CH3
с
TSCI
pyridine
H
E
A:
B:
C:
D:
E:
F:
G:
H:
1:
J:
Transcribed Image Text:Supplemental Assignment 3: Road Map: From the following data provide structures A through J. A J с B G J SOCI₂ 1) 9-BBN 2) H₂O₂, NaOHA CH3OH A H₂ Pd/Lindlar's cat. 1) 9-BBN 2) H₂O2, NaOH B 1) 03 2) Zn, H₂O D J KOH ethanol I 1) Hg(OAc)2, CH3OH 2) NaBH4, NaOH Br₂ H₂O 0= с + J + minor substitution products major minor PCC CH₂Cl₂ |= F i CH3CHCH + HCH CH3 с TSCI pyridine H E A: B: C: D: E: F: G: H: 1: J:
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