CHEM 2400

Homework 14: Synthesis Problems

Name: _______________________________ Date: _______________________

This set of problems has six sections. Please read the directions for each section carefully.
The “long” synthesis problems are the last section, and you will need additional paper to
write those out.

Part One: These questions are designed to help you start thinking “retrosynthetically.”

What is one way that you can make each of the following compounds? Put the starting
material in the blank and the inorganic reagent in the box over the arrow. I put an
example of what to do here:

H2
Pt

y
1)

"Nos
=>

2)

Brz

F
3)
Part Two: Same thing, but I took away the prompts. Just put the starting material on the
line, and the inorganic reagent over the arrow.

KCN

1)
Br

MCPBA
F
2)

KOH
3)

Bri

4)
K Fe

OH H2CrO4
X
5)

My
~
Br
6)

Brz
-
7)
or
light

O CHz: MgBr
#
8)
Azo
Part Three: Short answer synthesis problems.

For each reaction sequence shown, give the product that will result. This type of question
will help you prepare for the multiple choice style questions that you will have on the
exams.

OH

↓
V

OH
X

N
OA

↓ Br
-=8 a
*

=
+
=:
-

-
-

*
H

=
Bu

-
Bet Br I

Br
-

-
 Br
-
↓
:OMgBr

i
Ot Br

- -

#i
S X

Of &

on
=>
N
Part Four begins on the next page.

Part Four: Multiple Choice Synthesis problems.

1) What product results from the following reaction sequence?

a
Br KO:MgBr

2) What product results from the following reaction sequence?

r -Br

3) What product results from the following reaction?

g

4) What is the result of the following sequence of reactions?

OH

5) What product results from the following reaction sequence?

 z

6) What is the result of the following sequence of reactions?

7) What product results from the following reaction sequence?

 Oh

8) What is the result of the following sequence of reactions?

9) What product results from the following reaction sequence?

 S 8

10) What is the result of the following sequence of reactions?

11) What product results from the following reaction sequence?

12) What product results from the following reaction sequence?

 =>

13) What is the product of the following reaction sequence?

14) What product results from the following reaction sequence?

 =

I D

15) What sequence of reactions

Section Five is on the following page.

Section Five: Filling in the Inorganic Reagents.

The organic compounds that would be in a possible synthesis pathway are
already drawn out for you. You just have to fill in the inorganic compounds in the
boxes provided next to the arrows.

1) Fill in the missing reagents in the path to make the alkene from the ketone shown.

H2CrO4

CH3 :MgBr
ABr

Kot

2) Practice making propanal from 1 and 2 carbon units by adding the missing
reagents.

H2CrO4

My

3) The alkene (1-cyclohexyl-1-bromo propane can do any of the following reactions

shown. Please fill in the reagents to show how to get from the starting alkene to each
product shown below for practice.
 H2

ABr MCPBA

H20
+
H

Fe

Part Six: Please write out the longer problems on separate sheets of paper.
These are to help you practice doing the “long” synthesis problems on the exam. The
directions shown below are approximately what you would see on the exam.

Using benzene, cyclohexanone, or cyclohexane, any monofunctional compound with two

or fewer carbons, and any inorganic reagents you choose, synthesize the following
structures. You should attach separate pages showing the synthesis problems. 

1) 2) 3)

4) 5) 6)

7) 8) 9)
1)
OgBrg s

2)ENa Y NaNH
H

·
5) X

H NaHz
=A

kn A
N

Be right
&
7) W
BrB W
TNaNH2
Hzot

H = H

8)= : (NaNH yE-H >NaNHcI

Br

For
I

↑H
*
#30
H

#
Br