Download Exam 1 - Winona State University

351 Organic Chemistry II
Exam #1, June 24, 2013
Winona State University
Professor T. Nalli
Name ______________________________________
General Instructions: Write your name in the space provided above and on the provided Scan-tron
form. Do not put your name anywhere else in this exam book.
Make sure that you read each question carefully and provide complete answers. Time limit is 55
min. Exams must be turned in immediately upon my call of time up.
Grading will be on the basis of a highest possible score of 100 points.
I. Multiple Choice – 2 points each, 20 points total
II. Nomenclature/Structure – 2 points each, 20 points total
III. Synthesis – 5 points each, 15 points total
IV. Reaction Products – 5 points each, 40 points total
V. Mechanism - 10 points
1
I. Multiple Choice
1. Which of these compounds is the least soluble in water?
A. 2-octanol
B. methyl t-butyl ether C. 1-pentanol
D. diethyl ether
2. Which of these compounds is the weakest acid?
OH
SH
OH
A.
B.
E. isopropyl alcohol
SH
C.
D.
3. Which of these has the lowest boiling point?
SH
A.
O
B.
OH
C.
D.
OH
5. Which of these compounds is the least soluble in water?
A.
O
B.
S
C.
OH
D.
OH
6. Which of these compounds reacts with chromic acid to form a carboxylic acid?
A.
O
B.
S
C.
OH
D.
OH
7. Rank the following compounds in decreasing order of boiling points (highest to lowest)
CH3CH2CH2CH2OH
I
A. II>IV>I>III
CH3CH2OCH2CH3
II
B. I>IV>II>III
CH3OCH3
III
C. IV>I>II>III
D. III>II>I>IV
HOCH2CH2CH2OH
IV
E. IV>II>I>III
8. Rank the following alcohols in order of decreasing acidity (most acidic to least acidic).
A. I > II > III
F
F
B. III > II > I
OH
C. II > III > I
OH
F
D. I > III > II
F
II
I
OH
III
9. Which of the following reagents will react with an ester to form a primary alcohol?
A. OsO4
B. MeMgBr
C. NaBH4
D. LiAlH4
E. Mg, THF
10. Which reagent is often used for the deprotection of alcohols?
A. TBAF
B. THF
C. PCC
D. MCPBA
2
E. OsO4
II. (A) Give the structure of each of the following.
PCC
TBAF
THF
12-crown-4
II. (B) Give an acceptable name (common or IUPAC) for each of the following.
OH
OH
HO
SH
OMe
O
O
3
III. Propose a synthetic sequence that could be used to carry out each of the following transformations in
good yield.
O
1.
2.
OH
OH
O
Ph OH
3.
OH
OH
4
IV. Give the structure of the main organic product of each of the following reactions. Make sure to show
stereochemistry of the product where appropriate.
1.
OH
2.
OH
1. NaH
2. O 3. H2O
PCC
CH2Cl2
OH
3.
HBr
1. Mg, THF
4.
Br 2. Ph
O
3. H2O
O
1. LiAlD4
5.
2. H2O
HBr
6.
O
7.
KMnO4, OH-
O
O
8.
HS
1. NaOH
2. EtOTs
5
V. (a) Write the mechanism of the reaction shown, using curved arrows to show the flow of electrons in
each step. (b) Use the mechanism to explain the regioselectivity of the reaction.
H2S
O
OH
H+
SH
6