Chemistry 261 Quiz 3 Practice Fall 2013 The following quiz contains 32 questions valued at 1 point/question Name: ________________________________________________________

1. Cis-trans isomers are a. Diastereomers b. Enantiomers c. Stereoisomers d. Constitutional isomers e. More than one of the above E 2. Which of the following molecules is achiral?
H H H Cl Br Br Cl Cl H Br H Br Cl Br H Br H Cl

II

III

a. I b. II c. III d. More than one of the above e. None of the above C

3. Which of the following is true of any (R)-enantiomer?

a. It is dextrorotatory b. It is levorotatory c. It is an equal mixture of + & - rotations d. It is the mirror image of the (S)-enantiomer e. More than one of the above D 4. Which of the following represents (S)-1-Chloro-1-fluoroethane?
F Cl H CH3 H F Cl CH3 H F CH3 Cl

II

III

a. I b. II c. III d. More than one of the above e. None of the above D 5. Which of the following compounds would show optical activity? a. cis-1,4- Dimethylcyclohexane b. trans-1,4- Dimethylcyclohexane c. cis-1,4- Dimethylcycloheptane d. trans-1,4- Dimethylcycloheptane e. More than one of the above D

6. Of the compounds corresponding to the general name dichlorocyclobutane, how many are optically active? a. 0 b. 1 c. 2 d. 3 e. 4 C 7. If an optically active compound has a measured rotation of +5o in a 1 dm tube at a concentration of 10.0 g/50.0 mL, what is the specific rotation? a. +50o b. +25o c. +10o d. +1o e. +0.5o B 8. What is the % composition of a mixture of (S)-(+)-2-butanol, [a] = +13.52o, and (R)-(-)-2-butanol if the specific rotation of the mixture = -4.51o? a. 75% (R), 25% (S) b. 25% (R), 75% (S) c. 50% (R), 50% (S) d. 67% (R), 33% (S) e. 33% (R), 67% (S) D

9. Which of the following is a meso compound?

CH3 H H Br Br CH3 H3C H OH H OH CH3 H3C H CH3 H F F

I
a. I b. II c. III

II

III

d. More than one of the above e. None of the above D

10. Please name the following compound using IUPAC nomenclature rules
2 (C,C,H)

1 3 (C,H,H)

Name: (S)-3-chloro-2-methylhexane 11. Please completely name the following compound according to IUPAC rules
I

Name: (3R,4R)-3,4-diiodoheptane

12. How are the following structures related?

CH3 H H CH3

H CH3 H

CH3

a. Same compound b. Enantiomers c. Meso forms d. Diastereomers e. Conformational isomers A 13. How are the following structures related?
H CH3

a. Constitutional isomers b. Enantiomers c. Identical d. Diastereomers e. Not isomeric A

14. I & II are:

Br H

H Br

I a. Constitutional isomers
b. Enantiomers c. Identical d. Diastereomers e. Not isomeric C 15. How are the following compounds related?
CH3 Cl H CH3 H Cl Cl Cl CH3 H

II

CH3 H

a. Constitutional isomers b. Enantiomers c. Different conformations of the same molecule d. Diastereomers e. Not isomeric B

16. I & II are:

Cl

Cl

II

a. Constitutional isomers b. Enantiomers c. Identical d. Diastereomers e. Not isomeric B 17. I & II are:
HO OH

II

a. Constitutional isomers b. Enantiomers c. Identical d. Diastereomers e. Not isomeric D

18. Please select the rate law for the following reaction
CH3CH2CH2CHBrCH3 + OH- CH3CH2CH2CHOHCH3 + Br( RBr )

a. Rate = k [RBr] b. k [RBr] [OH-] c. k [RBr]2 [OH-] d. k [RBr] [OH-]2 e. Rate = k [RBr]2 [OH-]2 B 19. In an SN1 reaction, why doesnt increasing the concentration of the nucleophile increase the rate of reaction? Dissociation into a carbocation and leaving group is the rate determining step 20. Consider the reaction of 2-chloro-2-methylpentane with sodium iodide. What would be the effect on the rate of reaction if one were to simultaneously double both the 2-chloro-2-methylpentane and the sodium iodide? a. There would be no effect on rate b. Rate would increase 2x c. Rate would increase 4x d. Rate would increase 6x e. Rate would increase 8x B

21. Which of the following reactions proceeds with inversion of configuration at the carbon bearing the leaving group? a. SN2 b. SN1 c. E2 d. E1 e. All of the above A 22. What product(s) would you predict in the following reaction?
H H

CH3ONa CH3OH

CH3

Br

OCH3

CH3O

CH3

OCH3

CH3

Br

II

III

a. I b. II c. III d. An equimolar mixture of I & II e. None of the above B

23. By analyzing starting materials and products for the following reaction, which type of mechanism is occurring?

+
Br N3 N3

a. SN1 b. SN2 c. E1 d. E2 e. More than one of the above A 24. Which of the following alkyl chlorides is essentially unreactive in an SN2 reaction? a.
Cl

b.
Cl

c.
Cl

d.
Cl

e.
Cl

25. Which of the following is the strongest nucleophile in aqueous solution? a. Fb. Clc. Brd. Ie. All are equally strong D

26. Why is the reaction between sodium isopropoxide and isopropyl amine to generate diisopropyl ether not feasible? a. Because elimination would be favored by an E2 mechanism b. Because elimination would be favored by an E1 mechanism c. Because a mixture of substitution and elimination products would be formed d. Because there is no good leaving group available e. In fact, the reaction would proceed and give excellent yields D 27. Which of the following is not a good leaving group? a. C2H5Ob. Clc. Id. CH3CO2e. All of the above are good leaving groups A

28. Which would be the principal product(s) of the following reaction?

O O S O

CH3SNa CH3SH
SCH3 SCH3

II

III

IV

a. I b. II c. III d. IV e. More than one of the above C 29. The principal product(s) of the following reaction would be dictated by which mechanism?

NaCN DMF
Cl

a. SN1 b. SN2 c. E1 d. E2 e. None of the above B

30. Which would be the principal product(s) of the following reaction?

HO Br

80 oC

(CH3)2CHCH2O

II

III

IV

a. I b. II c. III d. IV e. More than one of the above E 31. Which would be the principal product(s) of the following reaction?
Li Br

THF

I
a. I b. II c. III d. IV

II

III

IV

e. More than one of the above A

32. Please synthesize 2,2,3,3-tetrabromohexane from propyne and n-propyl chloride (1) (2) (3) Deprotonate propyne with NaNH2 or NaH Add propyl chloride Isolate and add 2 eq. Br2 in CCl4

Hint: when you are developing a synthesis, learn to count carbons to see where your pieces are coming from. Work backwards this is known as the retrosynthetic approach. In this case 3 C from propyne and 3 C from n-propyl chloride, which, when coupled together places the alkyne bonds between C2 and C3 perfect for subsequent addition of 2 eq Br2