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 56 78 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 3 4 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 CH2Cl2 1 2 3 4 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 RCO 3H CH2Cl2 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. H2O2, NaOH 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 Page 3 of 3 Question 8 [1.6 pts] Regarding.

1. 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

2. 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

3. 1 2
3
4
56
78
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
3
4
5
6
7
8

4. 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
CH2Cl2
1
2
3
4
5
6
7

5. 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 RCO 3H
CH2Cl2
Question 6 [1.6 pts] Which one of the following statements
about Reaction 5 is correct?
Reaction 5
CH2Cl2
A
B

6. Br
H
NaCN
cyanide ion at atom A
ct arises from front face attack by
cyanide ion at atom B
cyanide ion at atom A
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. H2O2, NaOH
1
2
3
4
5

7. 6
7 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

8. 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.

9. Reaction 9
OH H2SO41
2
3
4
5
6
7
8
9
10 12
11 13
Privacy issues and concerns
Privacy issues and concerns
Criteria
Ratings
Pts
Used headings for each section
Used headings correctly

10. 4.0 pts
Used Headings, but not spaced properly from text for
readability.
3.0 pts
Used headings incorrectly
2.0 pts
Did not use headings
0.0 pts
4.0 pts
A brief overview of what each scenario is about.
Provided a short summary of the issues presented by the
scenarios.
15.0 pts
Scenarios are moderately defined, concepts learned are
integrated in the analysis. Critical thinking is evident.
10.0 pts
Summarized the topic, said, and gave a few personal thoughts,
but few or no specific concepts.
9.0 pts
Summarized the scenario, but gave few or no personal thoughts.
8.0 pts
Not fully developed. Evident minimum amount of time was
spent on reflection..
5.0 pts
Topic 1 missing
0.0 pts
15.0 pts
Provided a clear definition of each issues associated with the
issues presented in the scenarios.
Privacy issues are well defined, concepts learned are integrated
in the analysis. Critical thinking is evident.
15.0 pts
Privacy issues are moderately defined, concepts learned are
integrated in the analysis. Critical thinking is evident.

11. 10.0 pts
Summarized the issues, and gave few personal thoughts , but
few or no specific concepts.
9.0 pts
Summarized the privacy issues, but gave few or no personal
thoughts or concepts.
8.0 pts
Evident minimum amount of time was spent on reflection..
5.0 pts
Topic 1 missing
0.0 pts
15.0 pts
Real Life Relation
RLR is well written and shows good relation to the chapter.
Critical thinking is evident.
10.0 pts
RLR is moderately defined and summarized. Critical thinking is
moderately evident.
5.0 pts
RLR is not fully developed. Evident minimum amount of time
was spent on reflection.
1.0 pts
RLR missing
0.0 pts
10.0 pts
Mechanics (Grammar, spelling)
Exceptional writing mechanics
6.0 pts
At least three spelling and/or grammar errors were detected.
Overall comprehension was not impacted.
4.0 pts
Significant number of spelling and/or grammar errors were
detected. Comprehension is manageable with difficulty.
2.0 pts

12. Significant number of spelling and/or grammar errors were
detected. Comprehension was greatly impacted.
0.0 pts
6.0 pts
If your writing mechanics are graded as 2 or less, please check
in with the Campus Writing Center for assistance:
http://www.cwu.edu/learning-commons/university-writing-
center
0.0 pts
Writing Assistance
0.0 pts
0.0 pts
Total Points: 50.0