CH
3
CH
CH
3
OH
Na
2
Cr
2
O
7
H
+
/ H
2
O / cool
benzoic acid
SOCl
2
reflux
LiAl(O-t-Bu)
3
H
CH
3
CH
CH
CH
3
O
3
Zn / H
2
O
CH
2
CH
2
CH
2
OH
CrO
3
H
+
/ H
2
O
SOCl
2
reflux
(CH
3
CH
2
-)
2
CuLi
CH
C
CH
2
CH
3
Hg
+
2
/ H
+
/ H
2
O
reflux
CH
2
CH
2
CH
3
Br
NaOH(aq)
PCC
Cl
O
AlCl
3
S
S
H
H
ButLi
CH
2
CH
2
Br
H
3
O
+
HgCl
2
benzoic acid
2 CH
2
CH
3
-Li
H
3
O
+
CH
3
C
CH
3
O
CH
CH
3
O
2
CH
CH
2
CH
3
O
O
CH
CH
2
CH
3
O
O
CHO
O
CH
2
CH
3
OH
PBr
3
KCN
i-Bu
2
AlH
H
+
/ H
2
O
H+
H
2
O
SOCl
2
CHM 2211
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- Spring '09
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- Reaction, Carboxylic acid, CrO, CH3 CH2 CH, CH3 CH CH
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