Practice Exam 2 Name___________________________________

Class Roll #______________

PART I: (40 points, 4 points each) MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.

1.

Whatisthemajorproductofthefollowingreaction?

OH

CH2OH

II

CH3

III

CH3 OH

IV

CH3

V
HO

CH3

OH

A) I

B) II

C) III

D) IV

E) V

2.

Whichofthefollowingisthemoststablecarbocation?Addchoices

A) I

B) II

C) III

D) IV

E) V

3. Which of the following compounds is the major product when 1-hexyne is treated with excess HBr? A) 1,1-dibromohexane B) 1,1-dibromohexene C) 1,2-dibromohexene D) 1,2-dibromohexane E) 2,2-dibromohexane

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Practice Exam 2 Name___________________________________

Class Roll #______________

4. Which of the following statements is incorrect about benzene? A) The carbon-hydrogen bond lengths are all the same. B) It has delocalized electrons. C) All of the carbon atoms are sp hybridized. D) The carbon-carbon bond lengths are all the same. E) All twelve atoms lie in the same plane. 5. Which of the following pairs are resonance structures?
CH3 CH3 CH2 CH3 CH3 CH3

I
and

II
and

III
and

CH3

CH3

CH3

IV
and

V
and

A) I

B) II

C) III

D) IV

E) V

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Practice Exam 2 Name___________________________________ 6. Which of the following is the most stable diene?

Class Roll #______________

II

III

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

V E) V

7. Which of the following is aromatic?

A) I

B) II

C) III

D) IV

E) V

8. What purpose does FeCl3 serve in the electrophilic aromatic substitution reaction between chlorine and benzene? A) It serves as a Lewis acid catalyst by reacting with the Cl2 and thereby activates it toward attack by benzene's electrons. B) It functions by destabilizing the carbocationic intermediate and thereby increases the rate of H+ loss. C) It functions by destabilizing the benzene through formation of a -complex. D) It serves as a radical initiator to produce the chlorine radical needed to propagate the chain reaction. E) It serves as a Lewis base catalyst by reacting with Cl2 to generate chloride ions.

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Practice Exam 2 Name___________________________________

Class Roll #______________

9. A and B are stereoisomers. They are nonsuperimposable and are mirror images of one another. Which of the following best describes the relationship between A and B? A) diastereomers B) structural isomers C) constitutional isomers D) enantiomers E) cis-trans isomers

10. Which of the following is not true of enantiomers? A) They have the same chemical reactivity with non-chiral reagents. B) They have the same melting point. C) They have the same specific rotation. D) They have the same boiling point. E) They have the same density.

PART II: (40 points, 4 points each) SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.
11. Whatistheproductinthefollowingreactions?

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Practice Exam 2 Name___________________________________

Class Roll #______________

12. Drawthemajororganicproductgeneratedinthereactionbelow.

HCl

H3C

CH3

13. Drawanacceptablestructurefor3-sec-butyl-1-heptyne.

14. Drawtwootherresonancecontributorsforthefollowingcompound:

15. Orderthefollowingmoleculesindecreasingorderofstability:

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Practice Exam 2 Name___________________________________

Class Roll #______________

16. Providethestructureofthemajorproductwhichresultsfrom1,2-additionofHBrtothedieneshownbelow.

17. Thefollowingmoleculeisnotaromatic.Why?

18. Whatistheroleofbenzeneinthefirststepofanelectrophilicaromaticsubstitutionreaction?

19. Isthemoleculeshownbelowchiralorachiral?

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Practice Exam 2 Name___________________________________

Class Roll #______________

20. Drawthestructureof(S)-1-bromo-1-chloropropane.Takeparticularcaretousesolid-wedgelinesanddashed linesinthestructuretoshowthestereochemistryaroundtheasymmetriccenter

Part III Using short phrases, sentences or drawings, answer the following questions
21. (10points)Completethefollowingreactionandprovideadetailed,step-by-stepmechanismfortheprocess.

22. (10points)Providethemajorresonancestructuresoftheintermediateinthereactionofbenzenewiththegeneric
electrophileE+.

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