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Organic Chemistry Exam III - Seton Hall University, Prof. John R. Sowa, Jr., Exams of Organic Chemistry

A past exam from seton hall university's organic chemistry course (chem 2313) taught by prof. John r. Sowa, jr. The exam, dated november 17, 2006, consists of multiple-choice and reaction mechanism questions. Students were required to write mechanisms, draw reaction coordinate diagrams, and identify products and reaction mechanisms.

Typology: Exams

2009/2010

Uploaded on 02/25/2010

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Name_______________________________
Chem 2313
Organic Chemistry Lecture
Seton Hall University
Instructor: Prof. John R. Sowa, Jr.
November 17, 2006
Exam III
100 points
Q1________
Q2________
Q3________
Q4________
Q5________
Total_______
Good Luck!
pf3
pf4
pf5

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Download Organic Chemistry Exam III - Seton Hall University, Prof. John R. Sowa, Jr. and more Exams Organic Chemistry in PDF only on Docsity!

Name_______________________________

Chem 2313

Organic Chemistry Lecture

Seton Hall University

Instructor: Prof. John R. Sowa, Jr.

November 17, 2006

Exam III

100 points

Q1________

Q2________

Q3________

Q4________

Q5________

Total_______

Good Luck!

1) (16 points) Reaction Mechanisms

a) (15 pts) Write a mechanism that explains the formation of the products I and II of the

following solvolysis reaction. Show all important intermediates.

OH

CH 3 OH

H 2 SO 4 (cat) OCH 3 OCH 3

I II

b) (1 pt) Does this above reaction occur by an SN1 or SN2 mechanism?

3) (25 Points, 5 pts ea) SN1 vs. SN2 Reactions

Write the product(s) of the following reactions and indicate whether the reactions follow an SN 1

or SN2 mechanism. Show stereochemistry.

i)

ii)

OH

HBr (conc.)

H 2 O

SN 1 or SN 2

KI

acetone

Br

iii)

KCN

acetone

H 3 C (^) Br H CH 3

iv)

CH 3 OH

v)

AgNO 3

CH 3 OH

Cl Cl

4) (24 points) Transformations.

Complete the following transformations by supplying the missing reagents, reactants or products.

Show correct stereochemistry where appropriate.

i)

ii)

iii)

OH S O O Cl

pyridine

A

KI, acetone

B

Br Br

xs CH 3 NH 2

C

(Hint: cyclic product, C 5 H 11 N)

OH CH 3 EtO 2 C N N CO 2 Et

PPh 3

Ph OH O

D

iv)

v)

F

E

PBr 3

Br

Cl (^) SPh