FLORIDA INTERNATIONAL UNIVERSITY Department of Chemistry & Biochemistry CHM 2210-U02 ORGANIC CHEMISTRY I Fall 2012

PRACTICE EXAM IV

Dr. Keller

CHM 2210-U02 Fall 2012 Practice Exam IV, Page 2 FLORIDA INTERNATIONAL UNIVERSITY Department of Chemistry Dr. Keller
1. What is the product of the reaction:

PRACTICE EXAM IV 3.

CHM 2210-U02 Fall 2012

What would be the major product of the following reaction?

OH

TsCl

tosylate

NaI acetone

CH3 I

CH3 I I CH3 I III IV II

CH3

OTs

CH3

a. I b. II c. III d. IV e. an equimolar mixture of I and II

2.

Which reducing agent is best for accomplishing the following reduction:

O C OH OH

4. How many different monochlorination products, not counting stereoisomers, can be prepared from 2,4-dimethylpentane by free radical chlorination?

CH3
O H HO H

CH3

CH3 CH CH2 CH CH3

a. LiAlH4 b. NaBH4

c. B2H6 d. H2/Pd

a. b. c. d. e.

2 3 4 5 6

CHM 2210-U02 Fall 2012 Practice Exam IV, Page 3 5. What is the major product of the following reaction: 8. Which reaction is an oxidation?
O O RCOH O RCH O c. RCH2OH d. Two of these RCOH

CH2OH

Na2Cr2 O7 H2SO4

a. RCH b. RCH2OH

a.

CH2OCrO3 H c.

O C H

CH2OH b. OH d.

O C OH
9.

e. All of these

Which statement is not true concerning trans2-butene. a. Addition of Br2 yields meso-2,3dibromobutane. O b. Ozonolysis yields only CH3 C H c. It is more stable than cis-2-butene. d. Its hydrogenation is more exothermic than that of cis-2-butene. e. Reaction with cold, dilute permanganate gives CH3CH(OH)CH(OH)CH3

6.The best reagent to accomplish this reaction would be:

OH H2C CHCHCH3 OH O CH CH CHCH3

a. H2O/H b. O3

c. cold, diluteKMnO4 d. O C O-OH

10. The product of this reaction would be:

O
7. Which reagent would not bring about this transformation:

CH3O Na CH3OH

RCH2OH
a. b. c. d. Cl2 SOCl2 HCl and ZnCl2 HBr

RCH2X

OH a. (CH3)2CHCHCH2 OH

OCH3 c. (CH3)2CHCHCH2 OH

O OH b. (CH3)2CHCHCH2 OCH3 d. (CH3)2CHCCH 3

CHM 2210-U02 Fall 2012 Practice Exam IV, Page 4 11. Which of the following would provide the best yield of (R)-2-iodooctane? a. (R)-2-octanol + HI b. (S)-2-octanol + HI c. (R)-2-octanol +NaI d. (R)-2-octanol + TsCl, then NaI e. (S)-2-octanol + TsCl, then NaI
c.

14. What is the major organic product from this sequence of reactions?
CH3 1. O 3
2. Zn/HOAc

CH3
a. b.

CH3 OH O
d.

O CH3 OH SCH3

O H

12. What is the product of this reaction:

15. How could this transformation be effected?

O C OCH3 O C OCH3

O + HCl
HO a. OH Cl b. e. b and c Cl c.

?
O OH

a. Na2 Cr2O7 in H3 O b. NaBH4

c. H2/Pd d. LiAlH4

d. a and c

13. Which reagent(s) would cleanly transform butyl alcohol into butyl bromide? a. HBr b. PBr3 c. NaBr/H2O/ e. all of these

16. Which set of reagents would be best for this conversion?

OH

d. more than one of these

OH

a. CH3CO3H, then H3O+ b. KMnO4/cold, dilute

c. O3, then (CH3)2S d. KMnO4/!

e. More than one of the above

CHM 2210-U02 Fall 2012 Practice Exam IV, Page 5 17. What are the major products from this sequence of reaction:

1. O3 2. Zn/HOAc
O a. CH3 CH2CH O b. CH 3CH 2CCH 2CH 3 + O c. CH3 CH2CCH 2 CH3 CH 2 d. CH 3CH 2CCH 2CH 3 + + O H H O O CH2 + O