CHEM 1315 Exam 3 Practice b

Name:______________________ Roll Number ________________

1. (40 points, 4 points each) Circle the correct answer. There is only one correct answer. a. What is the correct order of stability of the following radicals (more stable > less stable)?

A) B) C) D) b. A) B) C) D) c. A) B) C) D) E) d. A) B) C) D)

1>2>3 2>1>3 2>3>1 3>2>1 Which of the following statements is not true regarding the halogenation of alkanes upon treatment with a diatomic halogen and light? bromination is more selective for 3 positions than chlorination the reaction proceeds via a radical intermediate the reaction proceeds via a chain reaction this is a useful process for the formation of fluorides, chlorides, bromides and iodides What is the major product obtained from the monobromination of 2-methylbutane in the presence of light at room temperature? 1-bromo-3-methylbutane 2-bromo-2-methylbutane 2-bromo-3-methylbutane 1-bromo-2-methylbutane 3-bromo-2-methylbutane Which is a better nucleophile? H2O HO H2S HS

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CHEM 1315 Exam 3 Practice b

Name:______________________ Roll Number ________________

e.

The reaction of methyl iodide with sodium azide, NaN3, proceeds by an SN2 mechanism. What is the effect of doubling the concentration of NaN3 on the rate of the reaction? A) B) C) D) E) the rate remains the same the rate decreases by a factor of 2 the rate increases by a factor of 2 the rate increases by a factor of 4 the rate decreases by a factor of 4 What is the major organic product obtained from the following reaction?
1 Br KOtBu tBuOH 3 O-tBu Br 4 O-tBu O-tBu 2

f.

A) B) C) D) g.

1 2 3 4 What is the major organic product obtained from the following reaction?
OCH3 1 Br NaOCH3 CH3OH OCH3 Br 3 4 OCH3 2

A) B) C) D)

1 2 3 4

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CHEM 1315 Exam 3 Practice b

Name:______________________ Roll Number ________________

h. A) B) C) D) E) i. A) B) C) D) E) j. A) B) C)

Which of the following reagents is the best one to use in order to convert methyl alcohol into methyl bromide? Br HBr Br2 NaBr Br+ What product is formed when 1,2-dimethylcyclohexanol undergoes acid-catalyzed dehydration? 1,2-dimethylcyclohexene 2,3-dimethylcyclohexene 1,6-dimethylcyclohexene 1,3-dimethylcyclohexene 2,2-dimethylcyclohexene What compound is formed when propanol is treated with pyridinium chlorochromate (PCC) in dry methylene chloride solvent?

D)

E)

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CHEM 1315 Exam 3 Practice b

Name:______________________ Roll Number ________________

2. (40 points, 4 points each) SHORT ANSWER. Draw the structure, or write the word or phrase that best completes each statement or answers the question. a. How many alkyl chlorides can be obtained from monochlorination of the following alkane?
H3C H3C CH3 CH3 H2 C CH3 CH3

b. Draw the major product for the following reaction

c. What is the major product formed when the following alkyl halide reacts with hydroxide ion in an elimination reaction?

d. Draw the major product(s) for the following reaction

CH2CH3 H Br CH3

CH3OH

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CHEM 1315 Exam 3 Practice b

Name:______________________ Roll Number ________________

e. Give the major product obtained when the following alkyl halide undergoes an E2 reaction?

f. Draw the major product from the following reaction.

g. Draw the major product for the following reaction

h. Draw the major product for the following reaction

H3C H2C H3C HO

CH3

H2SO4
heat

CH3

i. Draw the major product for the following reaction.

CH3

NaOCH2CH3 CH3CH2OH Page 5 of 6

CHEM 1315 Exam 3 Practice b

Name:______________________ Roll Number ________________

j. Draw the major product for the following reaction.

3. (10 points) Compare the two alkyl iodide compounds below and circle the molecule which would be expected to have a higher (faster) rate of reaction in the SN1 process. Provide a brief explanation in the space below for this behavior, using drawings and / or a sentence or two.

4. (10 points) There are four compounds with the formula C4H9Br. List them in order of decreasing reaction rate in an SN2 reaction.

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