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Practice Exam Chem

This document provides sample exam questions for a first chemistry exam covering topics like infrared spectroscopy, NMR spectroscopy, mass spectrometry, organic reactions, and IUPAC naming conventions. There are 23 multiple choice questions testing the identification of functional groups from spectroscopic data, prediction of products from reaction sequences, and selection of appropriate starting materials for synthesis.

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abhijit.salvekar
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© Attribution Non-Commercial (BY-NC)
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3K views

Practice Exam Chem

This document provides sample exam questions for a first chemistry exam covering topics like infrared spectroscopy, NMR spectroscopy, mass spectrometry, organic reactions, and IUPAC naming conventions. There are 23 multiple choice questions testing the identification of functional groups from spectroscopic data, prediction of products from reaction sequences, and selection of appropriate starting materials for synthesis.

Uploaded by

abhijit.salvekar
Copyright
© Attribution Non-Commercial (BY-NC)
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PDF, TXT or read online on Scribd
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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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