Download Chem 30B Spring 2004 QUIZ #1 KEY Weds April 14th / 30

Last
Name
First
Name
MI
Total Score
Student ID Number:
Circle the name of your TA:
MIKE
Discussion Section – Day:
35
ROB
/ 30
Time:
Chem 30B Spring 2004
QUIZ #1 KEY
(15 Min)
Weds April 14th
INTERPRETATION OF THE QUESTIONS IS PART
OF THE EXAM – DO NOT ASK FOR THE
QUESTIONS TO BE EXPLAINED TO YOU
USE CAPITAL LETTERS WHEN FILLING IN THE BOXES AND BE
CLEAR – IF WE CAN'T FIGURE OUT WHAT A LETTER IS, IT
WILL AUTOMATICALLY BE GRADED AS INCORRECT
***DO NOT OPEN THIS EXAM UNTIL INSTRUCTED TO DO SO***
Q
1
2
3
4
5
6
7
8
9
10
Total
C
D
D
D
E
A
D
D
B
D
30
ANSWER TO BONUS QUESTION
O
5
The fool doth think he is wise, but the wise man knows himself to be a fool – William Shakespeare
Questions 1–10 are worth 3 points each. The bonus is worth 5 points.
1. Which of the following chemical compounds will deprotonate an alcohol (R–OH) to give
the corresponding sodium alkoxide species (R–O– Na+)?
A
NaSH
B
NaCN
C
NaNH2
D
All of the above
E
None of the above
2. What is the correct name of the compound shown below?
HO
Br
A
(1S, 3R)-3-bromocyclopentan-1-ol
B
(1S, 3S)-1-bromocyclopentan-3-ol
C
(1R, 3S)-1-bromocyclopentan-3-ol
D
(1S, 3S)-3-bromocyclopentan-1-ol
E
(1R, 3S)-3-bromocyclopentan-1-ol
3. What is the MAJOR product of the bromination reaction shown below?
HBr
?
OH
Heat
A
C
B
Br
Br
D
Br
Br
E
Br
4. What is the correct chemical structure for propyl tosylate?
O
A
O
S
CH3
O
B
O
S
CH3
O
O
C
O
S
CH3
O
D
O
S
CH3
O
O
E
O
S
O
5. In the reaction scheme shown below, what are the reagents necessary for the exact
transformation as shown?
OH
(i)
(ii)
A
(i) TsCl
(ii) NaNH2
B
(i) PCl3
(ii) KCN
C
(i) H3PO4
(ii) HCN
D
(i) PBr3
(ii) K2Cr2O7
E
(i) MsCl
(ii) KCN
/ base
CN
6. What is the correct order of boiling points from LOWEST to HIGHEST of the following alcohols?
HO
OH
OH
1
A
2, 3, 1
B
3, 2, 1
C
3, 1, 2
D
1, 2, 3
E
1, 3, 2
OH
3
2
7. What is the product of the pyridinium chlorochromate (PCC) oxidation shown below?
OH
PCC
HO
CH2Cl2 (Solvent)
A
B
OH
H
O
C
OH
HO
O
?
D
O
OH
E
O
H
O
O
HO
O
8. What is the major product of the acid-catalyzed dehydration (elimination) reaction shown
below?
H3PO4
OH
Heat
?
(Elimination)
A
B
C
D
E
9. When a primary or secondary alcohol is oxidized with chromic acid (H2CrO4), the first
step of the mechanism involves the formation of a species called a chromate ester – what is
the oxidation state of the Cr atom in this species?
A
VII
B
VI
C
V
D
IV
E
III
10. What is the chemical structure of (2E)-3,7-dimethylocta-2,6-dien-1-ol?
A
HO
B
OH
C
HO
D
OH
E
OH
BONUS QUESTION: What is the product of the Pinacol rearrangement shown below?
Write your answer (just the structure) clearly in the box provided on the cover sheet to this
quiz. There will be NO partial credit – either your structure is right or wrong. The next
blank page can be used for working through the problem, but do not hand that part in.
OH
H2SO4
HO
(Pinacol Rearrangement)
?
Otherwise Blank Page