1. Treating 1- methylcyclohexene with H3 O+ would yield primarily which of these?

HO HO HO

I
HO

II
OH

III

IV

A) B) C) D) E)

I and V II III and V IV I, III and V

2.

The reaction of BrCl (bromine monochloride) with 1- methylcyclopentene will produce as the predominant product:
CH3 Br Cl CH3 Cl Br Cl CH3 Br Br CH3 Cl CH2Cl Br

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

+ enantiomer II

+ enantiomer III

+ enantiomer IV

+ enantiomer V

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3. What product would result from the following reaction? + HBr peroxides ?

Br Br Br HOO Br Br OOH

A) B) C) D) E)

I I II III IV V

II

III

IV

4. Which would be the major product of the reaction shown?

CH2CH3

1. Hg(OAc) 2, THF, H2O 2. NaBH4, NaOH

H OH H CH2CH3

OH H H CH2CH3

H H H CH2CH2OH

H H CH2CH3 OH

CH2CH O H

I A) I B) II

II

III

IV

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C) III D) IV E) V 5. What is the major product of the reaction: i) BH3, THF ii) H2O2,NaOH
CH3 CH3 OH CH3 OH CH3 OH

+ enantiomer

+ enantiomer IV

A) B) C) D) E)

I I II III IV Both III and IV

II

III

6. Which substance would undergo the following reaction?

? i. O 3 ii. Zn, HOAc O 4-Hexen-1-yne 3-methyl-1-hexene (E)-2-hexene (Z)-2-hexene 4-methyl-1-pentene
r

A) B) C) D) E)

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7. An alkene with the molecular formula C10 H18 is treated with ozone and then with zinc and acetic acid. The product isolated from these reactions is:
O O

What is the structure of the alkene?

II

III

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

8. Hydrogen atom abstraction from which position would yield the most stable free radical intermediate during the reaction of bromine with 2,2,3-trimethylpentane? A) C1 B) C2 C) C3 D) C4 E) C5

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9. Which of the following gas-phase reactions is a possible chain-terminating step in the light- initiated chlorination of methane? A) ClCl 2Cl B) Cl + CH4 CH3 + HCl C) CH3 + CH3 CH3 CH3 D) CH3 + ClCl CH3 Cl + Cl E) H. + CH3Cl CH4 + Cl. 10. Which would be the best way to carry out the following synthesis? ?
CH 3CH2 CHCH3 Br CH 3CH 2CH2 CH 2OH

A) B) C) D) E)

(1) HA, heat; (2) H3 O+, H2 O, heat (1) (CH3 )3 COK / (CH3 )3 COH; (2) BH3 :THF, then H2 O2 , OH(1) (CH3 )3 COK / (CH3 )3 COH; (2) H3 O+, then H2 O, heat (1) KOH, C2 H5 OH; (2) BH3 :THF, then H2 O2 , OH(1) KOH, C2 H5 OH; (2) HA, heat; (3) H3 O+, H2 O, heat

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11. What is the final product, C, obtained via the following reaction sequence?

Br2 h

A t-BuOK t-BuOH heat

OH

i) BH3, THF ii) H2O2, OH

OH

OH

OH

OH OH

I A) B) C) D) E)

II
I II III IV V

III

IV

12 What would be the final product?

O CH 3 H 3CC CH2 RCOOH

product

CH3OH, HA

final product

A) (CH3 )2 CHCH2 OCH3 B) (CH3) 2CCH3

OCH3

C) (CH3)2CCH2OH D) E)
OCH3 (CH 3 )2 CCH2 OCH 3 OH (CH 3 )2 CCH2 OCH 3 OCH3

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13. Which method would provide the best synthesis of ethyl isopropyl ether? A) (CH3 )2 CHONa + CH3CH2 Br B) CH3 CH2 ONa + (CH3 )2 CHBr C) H 2SO4, 140 oC CH 3CH 2OH + (CH3) 2CHOH D) H 2SO4, 180 oC CH 3CH 2OH + (CH3) 2CHOH E) CH3 CH2 ONa + (CH3 )2 CHOH

14. The following reaction,

HBr CH 3CH2CH2CH 2OH heat CH3CH2CH 2CH 2Br + H 2O

is probably: A) An SN1-type reaction involving the protonated alcohol as the substrate. B) An SN2-type reaction involving the protonated alcohol as the substrate. C) An E1-type reaction involving the protonated alcohol as the substrate. D) An E2-type reaction involving the protonated alcohol as the substrate. E) An epoxidation reaction. 15. (R)-3-Chloro-1-butene reacts with HCl by Markovnikov addition, and the products are separated by gas chromatography. How many total fractions would be obtained and how many would be optically active? A) One optically active fraction only B) One optically active fraction and one optically inactive C) Two optically active fractions D) One optically active fraction and two optically inactive E) Two optically active fractions and one optically inactive

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Answers
1. 2. 3. 4. 5. 6. 7. 8. 9. 10. 11. 12. 13. 14. 15. D D A B D E C C C B A C A B B

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