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Sample exam questions for First exam CHM 2211

1. The IR absorption due to the stretching of which of these carbon-hydrogen bonds occurs at the highest frequency?
H H H

I
H

II

III

IV
A) B) C) D) E) I II III IV V

2. How many signals would you expect to find in the 1 H NMR spectrum of CH3 OCH2CH2 OCH3 ? A) 1 B) 2 C) 3 D) 4 E) 5 3. Which proton(s) of the compound below would appear as a triplet in the 1 H NMR spectrum? I CH3 CH3CH2CH2-O-CH CH3 V IV III II I A) The protons on carbon II B) The protons on carbon I and V C) The protons on carbon III and V D) The protons on carbon III and IV E) The protons on carbon V

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4. A compound with the molecular formula C6 H15 N gave the following 1 H NMR spectrum: triplet, 0.90 quartet, 2.4 There were no other signals. The most likely structure for the compound is: A) CH3NCH2CH3 B)
CH 2CH 2CH 3 CH 3NCH2CH2CH 2CH 3 CH 3

C) CH3 CH2 CH2CH2 CH2 CH2 NH2 D) CH3CH2NCH2CH3 E)


CH2CH 3 CH 3CH 2CH2NCH2CH2CH 3

5. How many 13 C signals would 1,2-dimethylbenzene give?

A) B) C) D) E)

1 2 3 4 5

6. The data below from the molecular ion region of the mass spectrum of a halogencontaining compound are consistent with the presence of what halogen(s) in the original compound? M+ M+ +2 M+ +4 One Br One Cl One Br and one Cl Two Br Two Cl intensity 51.0 100.0 49.0

A) B) C) D) E)

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7. Which of the following resonance structures is not a significant contributor to the hybrid for the carbonyl group?
C O C O C O

II

III

A) B) C) D) E)

I II III Neither II nor III is important. All are significant contributors.

8. CrO 3 in H2 SO4 /H2 O will fail to give a positive test with which of these compounds? A) CH3 CH2 CH2CH2 OH B) CH3CHCH2CH3
OH

C) (CH3 )3 COH H D)
CH3CH2CH2C O

E) More than one of these

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9. The final product, D, in the following reaction sequence,


CH2 CH3CHOH CH3 CH2 O

PBr3

Mg ether

H3O +

, would be? A) CH 3CHOCH 2CH 2OH B) C) D) E)


CH3 CH 3CHCH 2CH2 Br CH 3 CH 3 CHCH 2 CH 2OH CH 3 CH 3CHOCH2 CH 3 CH3 CH 3CHCH 2 CH 3 CH 3

10. What is the final product of the following reaction sequence?


O

CH3I

Mg, Et 2O

i) ii) H3O
+

H2CrO4 acetone

A
OH

O O O

I
OH

II
O

III

IV

A) B) C) D) E)

I II III IV V

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11. What would be the product, A, of the following reaction ? i) NaBD4 A ii) H2O O A)
OD

B)
D OH OD
OH

C)
D

D) E) D
O

12. Which of the reagents listed below would efficiently accomplish the transformation of 3-methyl-3-cyclopentenone into 3- methyl-3-cyclopentenol?
O OH

A) B) C) D) E)

i) LiAlH4 ; ii) H2 O NaBH4 ,H2 O H2 , Pd A) and B) A), B) and C) of the above


C 6H 5 CH 3CH2 CH 2CCH 3

13.

OH Your task is to synthesize through a Grignard synthesis. Which pairs of compounds listed below would you choose as starting materials? O A)

CH 3CH 2CH 2Br and CH3 CC 6H 5

B) C)

O CH 3CH2 CH 2 CH and C 6H5Br O CH3 CH2 CHCH 3

and

C6 H5 CH

Br

D) More than one of these E) None of these

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14. Select the correct reagent(s) for the following reaction:


O CH 3 CCH2 CH 2CO2 CH 3
+

OH CH 3CHCH 2CH2 CH 2OH

A) B) C) D) E)

LiAlH4 /ether; then H3 O NaBH4 ; then H3 O+ H2 with Pt/C A) and B) A), B) and C)

15. What is an IUPAC name for this triene?


H CH3CH 2 H H H H CH 3 H

A) B) C) D) E)

(2E,4Z,6E)2,4,6Nonatriene (2Z,4E,6Z)2,4,6Nonatriene (2E,4Z,6Z)2,4,6Nonatriene (3Z,5Z,7E)3,5,7Nonatriene (3Z,5E,7E)3,5,7Nonatriene

16. Which of the following dienes would you expect to be the most stable? A) CH3 CH2 CH=CHCH2 CH=CHCH3 B) CH3 CH=CHCH=CHCH2 CH3 C) CH2 =CHCH2 CH2 CH2CH=CH2 D) CH2 =CHCH=CHCH2 CH2 CH3 E) CH3 CH2 CH=C=CHCH2 CH3

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17. Which is not an example of resonance?


I
CH2=CH CH2 .

. CH2 CH=CH2

II

CH2

CH2

III

CH2

CH3

+
.
CH2CH=CH CH2CCl3

IV A) B) C) D) E)

CH2=CHCH CH2CCl3

I II III IV None of these are examples of resonance

18. The accompanying diagram, which describes the fate of the intermediate in a reversible reaction, implies that:

E
B A

A) B) C) D) E)

reaction coordinate the less stable product forms more rapidly. the more stable product forms more rapidly. product B will predominate at equilibrium. the intermediate has a short lifetime. No conclusions can be drawn as to either reaction rate or product stability.

19. Which of these dienes can undergo the Diels-Alder reaction? A) 1,3-Pentadiene B) 1,4-Pentadiene C) 1,2-Butadiene D) 1,4-Cyclohexadiene E) All of the above can undergo the Diels-Alder reaction

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20. What would be the product of the following reaction?

+
CH2 O C CH 3 CH2 CHCCH3

heat

CH3 C CH

O C CH3

O C CH3

I
A) B) C) D) E) I II III IV All of these

II

III

IV

21. Which diene and dienophile would you choose to synthesize the following compound?
O H COCH 3 O O COCH 3

and O2
O

and
HC C COCH3

I
O O

II
O O CH 2 CH COCH 3

and III

and
CH 2 CH COCH 3

IV

A) B) C) D) E)

I II III IV None of these

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22. Which of the following could be used to synthesize 3-bromocyclopentene? A) Cyclopentene + Br2 , CCl4 , 25o B) Cyclopentene + NBS, CCl4 (ROOR) C) 3-Cyclopentenol + PBr3 D) Both A) and B) E) Both B) and C)

23. Which compound would have an UV absorption band at longest wavelength?


CHCH CH CHCH 3 CH2 CH CHCH 3

I
CH 2CH CH 2

II
CH CHCH 3

III

IV A) B) C) D) E) I II III IV V

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Answer Key
1. 2. 3. 4. 5. 6. 7. 8. 9. 10. 11. 12. 13. 14. 15. 16. 17. 18. 19. 20. 21. 22. 23. E B C D D D B C C E B D A A C B C B A C C E B

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