Chemistry 261 Exam 3 Practice Fall 2013 The following exam contains 31 questions valued at 3.0 points/question.

Name: _______________________________________________ 1. An alkane that can exhibit optical activity is a. Neopentane b. Isopentane c. 3-Methylpentane d. 3-Methylhexane e. 2,3-Dimethylbutane 2. Which of the following is a representation of (R)-2-butanol?
H H3C OH CH2CH3 H CH3 OH CH2CH3 HO H CH3 CH2CH3 HO CH3 H CH2CH3 H CH2CH3 OH CH3

I
a. III, IV

II

III

IV

b. I, II, III, IV c. I, IV, V d. I, III e. I, II, IV, V

3. Which of the following numbered compounds is the enantiomer of the molecule immediately below?
H H Br CH3

H Br H CH3 H

CH3 Br H H

CH3 H Br

II

III

a. I b. II c. III d. II & III e. None of the above 4. How many discrete1 dimethylcyclopropanes are there? a. 2 b. 3 c. 4 d. 5 e. 6 5. Below is shown the Fischer projection of one of the enantiomers of lactic acid. Using the Cahn-Ingold-Prelog system, what is the absolute configuration of the form shown? You must show your work for credit
O HO OH H

L-(-)-lactic acid

Absolute configuration: _________________________________________

Individual as opposed On the down low

6. A biological reduction of pyruvic acid to lactic acid generates a mixture with a specific rotation of -2.25o. What is the enantiomeric excess of the mixture, given the specific rotation of L-(-)-lactic acid is -2.50o?

Answer: _________________________________________________ 7. The specific rotation of L-(-)-lactic acid is -2.50o. If a sample of lactic acid showed a specific rotation of +2.00o, what would the percent composition of the lactic acid mixture be?

Answer: _________________________________________________ 8. Which of the following is/are meso?

Br Br Br H H Br H Br Br H Br H Br H

II

III

IV

a. I b. II c. III d. IV e. Two of the above 9. Please completely name the following compound using IUPAC nomenclature rules

Name: ______________________________________________________ 10. Please completely name the following compound according to IUPAC rules
O OH OH

Name: ______________________________________________________ 11. Please completely name the following compound according to IUPAC rules

H3C

CH 3

Name: ______________________________________________________ 12. How are the following structures related?

CH3 F H Cl F Cl H CH3

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

13. I & II are:

OH H

OH H H

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

II

14. I & II are:

OH

O Cl

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

OH II

15. I & II are:

H H I
a. Constitutional isomers b. Enantiomers c. Identical d. Diastereomers

SCH3 CHO

H H Me SCH3 Et CHO II

e. Not isomeric

16. Which is a true statement concerning the transition state of the rate determining step of an SN1 reaction? a. Structurally, it closely resembles the carbocation intermediate b. Both covalent bond breaking and bond making are occurring c. Formation of the transition state is an exothermic reaction d. The transition state has zero overall charge e. More than one of the above 17. Elimination reactions are favored over nucleophilic substitution reactions when a. high temperatures are used b. t-butoxide is used c. 3o alkyl halides are substrates d. the nucleophile is a strong base and the substrate is a 2o alkyl halide e. any of the above occurs 18. Which of the following would you expect to be the principal product(s) when

tert-butylbromide is reacted with sodium acetylide?

Br

HC

C:

Na

II

III

HC

CH

IV

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

e. None of the above

19. Which of the following is the poorest leaving group?

a. HOb. H2O c. TsOd. MsOe. CH3O20. Which would be the principal product(s) of the following reaction?
O O S

CF3 O

NaN3 DMF

N3

N3

I
a. I b. II c. III d. IV e. None of the above

II

III

IV

21. Please predict the product(s) of the following reaction sequence

1. NaI, acetone
Cl

2. CH3CO2Na, CH3CO2H

a.

b.

c.

d.

e. A mixture of (a) & (d)

22. The products for the following would be primarily dictated by which mechanism?
Br

CH3SNa EtOH

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

23. Which would be formed in the following reaction?

CH3 H3C H Br

CH3OH 55oC

OCH3 H3C H CH3 H3C H

CH3 OCH3

I
CH3 CH3

II

CH3

CH2

III

IV

a. I b. II c. III d. IV e. All of the above 24. Which would be the principal product(s) of the following reaction?
H3C H CH3 Br

CH3O/ CH3OH 55oC

H3C H

CH3 OCH3

H3C H

OCH3 CH3

II

H3C

CH3

H3C

III

IV

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

e. All of the above 25. Which would be the principal product(s) of the following reaction?
CH3 Br CH3 CH3

CH3CH2CO2H room temperature

O O

O O

II

III

IV

a. I b. II c. III d. IV e. None of the above

26. When t-pentylchloride undergoes solvolysis in aqueous ethanol at room temperature, which of the following is/are formed?

a.

OH

b.

OC2H5

c.

d.

e. All of the above

27. What is the principal product of the following reaction?

CH3CH2OH
Br

25 oC

OCH2CH3

OCH2CH3

II

III

IV

a. I b. II c. III d. IV e. None of the above 28. The products for the following would be primarily dictated by which mechanism?
O O S

CF3 O

CH3CH2OH

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

29. What is the principal product of the following reaction?

(CH3)2CHOH
Br

70 oC

OCH(CH3)2 OCH(CH3)2

II

III

IV

a. I b. II c. III d. IV e. None of the above 30. Please synthesize dipropyl ether beginning with any starting materials 3 carbons or less

31. Please synthesize 1,4-dioxan beginning with any starting materials 3 carbons or less