RETROSYNTHESIS PRACTICE PROBLEMS

1)
O
N O
N O O
O
O Br
OR OR

O O

O
N
O
OR

O O

2)

O N OH
H
OH Br

O O
O

3) CF3

CF3 O
O
H
N HO
H
Prozac

CF3 OH O

CF3 O
O
O Cl O
O O
O
O
4) O You may use any other reagents
you choose, provided they contain
O 7 carbons or less.
Ph
N
Ph Ph O N Cl-

(racemic) or CH2O/HNMe2

OH N
Ph
N
Ph Ph
Ph MgBr

5)
O
Ph Ph N You may use any other reagents
Ph you choose, provided they contain
HO
6 carbons or less.
Ph
O

Ph Ph Ph Ph
Cl
H H
O O

Et2CuLi

O
6)
O OH

O O

OH The key to this problem is recognizing

the need for a protecting group on the
ketone! The LiAlH4 needed to reduce the
carboxylic acid will also reduce the ketone.
O
7) O
Br

H
H
O
O

O MgBr
Cl O H
H
OH Once again, we must
O protect the aldehyde.
O H

O
8) O
H

HO
HO

Here we must protect the

-OH... one way to
O O accomplish this is to
convert it to Cl, then back to
Cl OH OH at the end.
HO HO

9) O
O
The retrosynthesis 10)
I illustrate is NOT O OH
step-by-step, but is VERY
the f irst-pass attempt CHALLENGING O
at seeing where things
probably come f rom: N OH
The f irst retrosynthetic
step would be a good HN
exam-type question
N
O
O
O Ph
OH

N
N
O O
O Ph
N O
O N O
O
Ph Cl
Br
N
O N
N N O
Ph O O
Ph
Ph Ph

11) NH2

NO2

NO2 NO2 O
There is an issue with
this order of steps; alkenes
are reduced by the same
conditions that convert
a nitro to an amine... OH O

12)
O
N

N
13) O
O

H
(racemic)

O O O
OH

H H H

14)
OH

ibuprof en

OH

O
OH

15) O OH

O O
16) O O

O O
OH

Here again, protection of the

ketone is necessary.
O O O O

OH O O

17) O
O
H

OH

O O
18) HO
H

HO O
OH
 19) O
O
N

H
N

20) O

N O You may use any other reagents

you choose, provided they contain
N HN 8 carbons or less.

H N
N
O
N
O You must go through
the amide because the
N secondary amine is
terribly difficult to alkylate.

21) O OH

OH OH

MgBr Br

OH OH
22) O
Br

O O

O O
MgBr
Cl OH

O O O

23) O

O O

OH

OH OH

OH
24) O

N H

O OH

LG OH
HO

HN
OH
LG LG OTs
H2N LG TsO

LG LG OTs
 25) THINK
O O CLAISEN O O O

EtO OEt

O O EtO O O O

EtO EtO

O O

26) Br
NH
H
CO2H amino acid:
think Strecker! O

Br
NH N
H
CN
N

27) O

hemiacetal O
HO NH OH
H2N
Ph

O O
H
N Br
Ph OH Ph
 28) O PPh3
O
O
O
H
O

O
O O

Cl
H
O
O
HO
O
29) O
O
Br
Enolate alkylation, Br O
but we can't just
easily alkylate
acetone...

O O OEt O O
O O

OEt
OEt
-keto ester:
Br think Claisen!

30) O

O
O OH O

O O