Practice Exam 3 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) The major type of reactions that alkanes undergo is: A) free radical addition reactions. B) electrophilic substitution reactions. C) nucleophilic substitution reactions. D) electrophilic addition reactions. E) radical substitution reactions. 2) Which of the following is the initiation step for the monobromination of cyclohexane?

A) I

B) II

C) III

D) IV

E) V

3) Which of the following best describes the carbon-chlorine bond of an alkyl chloride? A) ionic B) polar; + at carbon and - at chlorine C) nonpolar; no dipole D) polar; - at carbon and + at chlorine E) none of the above 4) Which of the following are the substitution products of the reaction shown below? CH3CH2Br + -OH ? A) CH3CH2OH + BrB) CH2CHBr + H2O C) HOCH2CH2Br D) CH3CH2Br + H + O-

E) CH2CH2 + Br- + H2O

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5) Which of the following alkyl halides gives the slowest SN2 reaction? A)

B)

C)

D) CH3CH2Cl E)

6) Which of the following factors has no effect on the rate of SN1 reactions? A) the nature of the alkyl halide B) the nature of the leaving group C) the concentration of the nucleophile D) the value of the rate constant E) the concentration of the alkyl halide

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7) What is the major product of the following reaction?

A) I

B) II

C) III

D) IV

E) V

8) Which of the following reagents can be used to oxidize 1 alcohols to aldehydes? A) K2Cr2O7 B) PCC C) MnO2 D) H2O2 E) KMnO4 9) What is the major product from the following reaction?

A) I

B) II

C) III

D) IV

E) V

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10) What is the major product for the following reaction?

10)

A) I

B) II

C) III

D) IV

E) V

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

Cl2

hv major product

12.

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13.

14.

15.

16.

17.

CH3 Br CH3 H3C

NaOMe MeOH major product

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18.

19.

20.

Part III Using short phrases, sentences or drawings, answer the following questions 21. (10 points) An alkane with the molecular formula C5H10 forms only one monochlorinated product treated with Cl2 and light. Give the structure of the products

22. (10 points) Rank the halogens of the alkyl halides series in decreasing order of leaving ability and explain why they have this order.

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