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Question 1

Points

ID: 2 3 CHEM 2301 4 Final Exam, December 12, 2012 5 Instructor: Dr. Alireza Fattahi 6 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.

1. With reference to compound Z drawn below, label each compound as an isomer, a

resonance structure, or neither. (9 points)

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)

C A B

The most reactive:

The least reactive:

4. For the given compound A, there are two chair conformers which can be interconverted.
Draw its more stable and less stable chair conformers in the given boxes. (10 points)

More stable chair conformer of A:

Less stable 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.

b.

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

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 artificial
sweetener. (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.

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

a)

[1 [2 [3

NBS
b)

hv

Note: 4 points for each product

c)

elimination

d)

[1] [2]

e)

f)

ROOR

g)

[1]
h)

[2] [3]

10. Devise a synthesis of the following compounds from the indicated compound, and any other
needed reagents. (a 12 points and b 10 points)

a)

from

b)

from

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

a)

b)

light

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

a.

b.

13. Circle the compound whose IR and NMR spectra match best with the following data:
You must assign each signal for the selected structure (10 points) IR absorption: 1718 cm1
1

H NMR: 1.4 ppm (triplet, 3 H), 2.4 ppm (singlet, 3 H), 4.4 ppm (quartet, 2 H), 7.2 ppm (doublet, 2H), 7.9 ppm (doublet, 2H)

B A

D C

10

1 14. Use the following IR and H NMR data to determine the structure of a compound with the

formula C3H6O2. You must assign important IR bands and 1H NMR peaks (10 points).
3H 1H 2H

11

15. An unknown compound has the molecular formula C8H10O . Deduce its structure from its 1H
and 13C NMR spectra. You must assign just the 1H NMR spectrum (the top one). Note: In 13C NMR spectrum, 3 small peaks around 78 ppm belong to the solvent used to dissolve this unknown compound. (12 points)
5H 2H 3H

12

13

14

15