chem 2301-final exam

8/13/2019 CHEM 2301-Final Exam

1/15

1

Last Name: First Name: Question Points

1

ID:2

3

CHEM 2301

4

Final Exam, December 12, 20125

Instructor: Dr. Alireza Fattahi6

7

8

9

10

11

12

13

14

Time: 2 hours 15

Total

Note: IR and NMR data as well as Periodic Table

are given on Pages 13, 14, 15.


2/15

2

1.With reference to compound Z drawn below, label each compound as an isomer, aresonance structure, or neither. (9 points)

a b c

Z

a: b: c:

2.Circle the stronger acid. Explain briefly your choice (6 points).

Explain:

3.In the following alcohols, determine the most reactive and the least reactive alcohol in

Dehydration? (6 points)

A B

C

The mostreactive: The least reactive:


3/15

3

4.For the given compound A, there are two chair conformers which can be interconverted.

Draw its more stableand less stablechair conformers in the given boxes. (10 points)

Morestable chair conformer of A:

Lessstable chair conformer of A:

5.For each of the following pairs of compounds, indicate whether they are enantiomers,

diastereomers, or the same compound (each 5 points)

A

a.

b.


4/15

4

6.For the following alkyl halides, answer each question. (12 points, 3 each)

A B C

a)The most reactive one in elimination reaction with CH3OH :

b)The most reactive one in elimination reaction with-OC(CH3)3 :

c)The most reactive one in hydrolysis:

d)The most reactive one in reaction with-OH in substitution reaction:

7.In the given boxes, name the five indicated functional groups for Aspartame, an artificialsweetener. (10 points, 2 each)

8.Answer the following questions about compound A. (10 points)

a. Label the weakest CC bond.b. Label the strongest CH bond.c. Explain why bond (1) and bond (2) are different in length, even though they are both C

C single bonds.


5/15

5

9.Draw the product of each reaction. Where appropriate, specify the stereochemistry.(5 points each)

2

3

1

NBS

hv

Note: 4 points for each product

elimination

-

-[2]

[1]

,

a)

b)

c)

d)


6/15

6

-

ROOR

[2]

[3]

[1]

e)

f)

g)

h)


7/15


8/15

8

11.Draw a stepwise mechanism for the following reactions. (each 12 points)

light

a)

b)


9/15

9

12.For each part (aand b), from the given compounds, circle the one that best fits the givenIR spectrum. (7 points each)

a.

b.


10/15


11/15

11

14.Use the following IR and1H NMR data to determine the structure of a compound with the

formula C3H6O2. You must assign important IR bands and1H NMR peaks (10 points).

3H

2H

1H


12/15


13/15


14/15

14


15/15

15

chem 2301-final exam

Documents