Exam IVO

Page Clearly write the first two

Name: ANSWER KEY letters of your last name here
KE
1 ______/15

2 ______/12 First and Last Name

Not Initials

3 ______/12

4 ______/15

5 ______/14

Be Careful
6 ______/10

7 ______/12

8 ______/10

Name ______/(-2)

ABAQ ______/(-5)

TCP ______/(-5)

Total ______/100 IN A PREVIOUS SEMESTER, 1/5 of the class

missed this Acid/Base Arrow Question. Will you?
Exam IVO

Name: ANSWER KEY First and Last Name

Chem 345
Fall 2016
Exam IVO
1.) Single Step Breakdown Problem: Each of these molecules can be made
by an Aldol, Michael, Claisen, Mannich, or Umpolung reaction/mechanism.
Write the name of the reaction above the arrow, and write the starting
material(s) for the reaction. (3 pts each, 15 points total).

A.
Umpolung

O O
OH
O

B. Aldol

O O

O O
C.
O O Claisen HO
MeO
HO or
O
O
HO
OMe

O
D. O
Michael
O
O or
O
O

O
E. Mannich

H
N
N

O
O
Exam IVO

2.) Predict the major carbon containing product(s) of the following sequence.
You do not have to worry about stereochemistry for this question.
(3 points each, 12 points total).
S
O O
A.
O N OH
NEt3
R

1.) O
O O
B. O

OMe O

2.) H3O +

O
C. O
NaOMe
O
MeOH

C9H14O

D. 1.) MeLi, Et2O OH

2.) H3O +
N
3.) NaBH 4,EtOH
Exam IVO

3.) Fill in the boxes. The second box in each sequence may represent one,
two, or three steps, but no more (3 points each, 12 points total).

A.) B.) O
O

1.) HSCH2CH2SH
HCl LDA, Et2O
2.) BuLi, Et2O

O
S S

Li

1.) 1.) Et2O

Br

O
2.) HgCl2, H2O
2.) H3O +

O
O

mixture of stereoisomers

HO
Exam IVO

4.) Write the mechanism for the following reaction. Draw all curved arrows.
Draw the major resonance structure of resonance stabilized carbocations or
carbanions except in umpolung reactions. (15 points).

O O O
H2SO 4
H 2O
O
Exam IVO

5.) Provide an efficient synthesis of the following molecule. All carbons

must ultimately come from benzene or materials containing five carbons or
less. Your sole sources of deuterium are DCl, NaBD4, LiAlD4, D2O, and
CD3OD. Show intermediate products along the way. Any Grignard reagent
or organolithium except BuLi must be synthesized. (14 points total)

O D D

Br
N
H
Exam IVO

6.) Using the indicated starting material and any molecules that do not
contain deuterium, write an efficient synthesis of the indicated target.
Show intermediate products along the way. Any Grignard reagent must
or organolithium must be synthesized except for BuLi.
(10 points total)
Exam IVO

7.) Write the missing reactant(s) for each of the following. Some of these
require multiple steps. Be sure to delineate separate steps with 1.), 2.), etc…
(4 points each, 12 points total)

A. O

O + O

NaOMe
MeOH

1.) NaNO2, HCl,

B.
2.) CuCN, H2O
+ 3.) LiAlH 4, Et2O
NH2 4.) H3O +
5.) NEt3
NH
O

O
Cl

C. 1.) CD3MgBr, Et2O

2.) H3O +
O OH

O + CD3
CD3
Exam IVO

8a.) Compound 8 has the formula C8H7N.

Calculate the DBE 6 (2 points) (8*2+2+1-7)/2=6

The IR shows an absorbance at 2226 cm-1.

Nitrile
1
8b.) Use the H NMR spectrum to solve compound 8’s structure. Write your
structure in the rectangle provided. All signals are shown. Assign protons a-
e to the corresponding protons on your structure. Only the structure and
assignments in the rectangle on this page will be graded. (8 points).

a N
d C

c e