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© S.

Lievens January 2012


University of California, Davis For use with UCD Chem 118 Series
118 B Practice Syntheses
Show how you would carry out the following syntheses using inorganic or organic
reagents. Include the reagents you would need for each step and the structure of
the intermediate products formed in each step. Some problems have more than
one possible answer. Problems A-O approximately cover the reactions found in
Volhardt and Schore chapters 11-13, problems P-X cover approximately chapters
14-16, and problems Y-AK cover chapters 11-18 with emphasis on chapters 17
and18.
Br OCH3
A) O Cl

Br
B)
Br
Br Br
© S. Lievens January 2012
University of California, Davis For use with UCD Chem 118 Series
Br
Br

C)
O Br

Br Cl

D) Br
Cl
© S. Lievens January 2012
University of California, Davis For use with UCD Chem 118 Series
OH
OH
E) Cl
Cl OH

O
F)
© S. Lievens January 2012
University of California, Davis For use with UCD Chem 118 Series
O
Br
G)
O

O
H) Cl
Br
© S. Lievens January 2012
University of California, Davis For use with UCD Chem 118 Series

Br
I)
OH

Br

HO

J)
Cl OH
© S. Lievens January 2012
University of California, Davis For use with UCD Chem 118 Series

K)
Cl O
O

L) O
O
OH
© S. Lievens January 2012
University of California, Davis For use with UCD Chem 118 Series

OH
Br

M)
OH

Br OH
N)
O
H OH
© S. Lievens January 2012
University of California, Davis For use with UCD Chem 118 Series

Br OH

O)
Br OH

O
O2N
P)
© S. Lievens January 2012
University of California, Davis For use with UCD Chem 118 Series

Q)
O2N Br

OH OH
Cl NO2
R)

O
© S. Lievens January 2012
University of California, Davis For use with UCD Chem 118 Series

NH2
S)
Cl Cl

O
T)
N
H
© S. Lievens January 2012
University of California, Davis For use with UCD Chem 118 Series
O O
HN HN
O2N CH2CH3
U)

HN

V)
Cl

O
© S. Lievens January 2012
University of California, Davis For use with UCD Chem 118 Series

Br NO2
W)

X)
Cl
NH2
© S. Lievens January 2012
University of California, Davis For use with UCD Chem 118 Series
O O
Y) I
H H

O
Z) H
© S. Lievens January 2012
University of California, Davis For use with UCD Chem 118 Series

O
CH2 Br
AA)

OH
AB)
O
Br Cl
© S. Lievens January 2012
University of California, Davis For use with UCD Chem 118 Series

H
AC) OH
O

HO
CH2
AD)
CH3
© S. Lievens January 2012
University of California, Davis For use with UCD Chem 118 Series
Br

OH Br
AE)

AF)
© S. Lievens January 2012
University of California, Davis For use with UCD Chem 118 Series
Br
O
AG) H
Br
OH

HO

AH)
Br
© S. Lievens January 2012
University of California, Davis For use with UCD Chem 118 Series

AI)

HN

Br
O Br

AJ) H H
Br
Br
© S. Lievens January 2012
University of California, Davis For use with UCD Chem 118 Series

O O
O
AK)

NH2