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Chemistry 331 Winter 2017

24 Feb

Page 1 of 3
Chemistry 331 Winter 2017
Quiz 4 Document
General comments
Quizzes are open-book and not proctored. The quizzes account for 60 course points since your lowest quiz score will be dropped.
That said, it will be possible to earn up to 16 points on each quiz. It will therefore be possible for you to earn up to 4 additional
points towards your overall course grade. Answers not submitted by the deadline will not be graded. This course does not have
make-up quizzes.
Instructions
1. Print this Quiz 4 document
2. Once you have roughed out your answers on paper select the “Quiz 4” item in the
Quiz Materials module on Canvas
3. Select/enter your answers. You may exit the “Quiz 4” item at any time and resume answer selection/entry later. Answer
selections/entries can be changed at any point prior to submission.
4. All answer selections/entries must be selected/entered and submitted by
10:00 am (Pacific Time) Monday February 27
Please note that Dr. Walker cannot answer questions related to an active quiz, as this would impose an unfair disadvantage to the
other members of the class. Thank you for your anticipated understanding.
Question 1 [1.6 pts] What carbon atom will be bonded to a bromine atom in the major organic product(s) of Reaction 1?
Reaction 1
HBr
1
2
3
4
5
6
7 8
Question 2 [1.6 pts] Which carbon atom bears the positive charge in the carbocation that arises from the rearrangement
implied by the curved arrow notation shown in
Figure 1?
Figure 1
H
1 2
3
4
6 5
8 7
9
Question 3 [1.6 pts] What carbon atom will be bonded to an oxygen atom in the major organic product(s) of Reaction 2?
Reaction 2
H2O, H2SO4
1
2
4 3
5
6
7
8
9
10
11

Page 2 of 3
Question 4 [1.6 pts] What carbon atom will be bonded to a chlorine atom in the major organic product(s) of Reaction 3?
Reaction 3
Cl2 excess NaBr
CH
2Cl2
1
2
4 3
5
6
7
8
9
10
11
Question 5 [1.6 pts] How many organic products are formed in Reaction 4? Hint / The alkenes react sequentially, rather
than at the same time. Each structural isomer counts as one organic product. Each stereoisomer counts as one organic
product.
Reaction 4
excess RCO3H
CH
2Cl2
Question 6 [1.6 pts] Which one of the following statements about Reaction 5 is correct?
Reaction 5
CH2Cl2
A B

Br

H
NaCN
q The major organic product arises from front face attack by cyanide ion at atom A
q The major organic product arises from front face attack by cyanide ion at atom B
q The major organic product arises from back face attack by cyanide ion at atom A
q The major organic product arises from back face attack by cyanide ion at atom B
Question 7 [1.6 pts]
What carbon will be bonded to an oxygen atom in the major organic product(s) of Reaction 6?
Reaction 6
1. BH3/THF
2. H
2O2, NaOH
1
2
3
4
5
7 6
8
9
10
11
12
13
14
15

Page 3 of 3
Question 8 [1.6 pts] Regarding Reaction 7 which of the labeled carbons become sp2 carbons of C=O groups of
aldehydes? Select all that apply.
Reaction 7
1. excess O3, -78oC
2. excess Zn, acetic acid
a b
c
d
e
f g
h
i
j
Question 9 [1.6 pts] How many organic products are formed in Reaction 8? Hint / The alkenes react sequentially, rather
than at the same time. Each structural isomer counts as one organic product. Each stereoisomer counts as one organic
product.
Reaction 8
excess H2, Pt
Question 10 [1.6 pts] What carbon atoms will be bonded to an oxygen atom in the major organic product(s) of Reaction
9
? Select all that apply.
Reaction 9
OH
1 H
2SO4
2
3
4
5
6
7
8
9
10 12
11 13

 
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Posted by on February 24, 2017 in Academic Writing

 

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