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Draw all likely alkene products in the following reaction and circle the product you expect to predominate. Draw all likely alkene products in the following reaction and circle the product you expect to predominate.

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Show the carbocation intermediate formed during the synthesis of geraniol by SN1 reaction. Show the carbocation intermediate formed during the synthesis of geraniol by S<sub>N</sub>1 reaction.

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Which halide reacts most rapidly via an SN2 mechanism?


A) Which halide reacts most rapidly via an S<sub>N</sub>2 mechanism? A) B) C) D) E)
B) Which halide reacts most rapidly via an S<sub>N</sub>2 mechanism? A) B) C) D) E)
C) Which halide reacts most rapidly via an S<sub>N</sub>2 mechanism? A) B) C) D) E)
D) Which halide reacts most rapidly via an S<sub>N</sub>2 mechanism? A) B) C) D) E)
E) Which halide reacts most rapidly via an S<sub>N</sub>2 mechanism? A) B) C) D) E)

F) C) and D)
G) D) and E)

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Which of the following best explains why SN1 reactions involving a neutral reactant are faster in polar solvents?


A) The substrate is more soluble in polar solvents.
B) The substrate is less soluble in polar solvents.
C) The nucleophile is solvated by polar solvents.
D) Solvation by polar solvents stabilizes the carbocation.
E) Solvation by polar solvents stabilizes the transition state.

F) A) and E)
G) C) and D)

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Provide the major organic product(s)in the reaction below. Provide the major organic product(s)in the reaction below.

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Rank the species below in order of leaving group capabilities in SN2 reactions (worst leaving group to best): CH3O-,H2O,C6H5SO3-,H2N-.

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H2N- < CH3O- <...

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Provide the structure of the major organic product in the following reaction. Provide the structure of the major organic product in the following reaction.

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How many distinct alkene products are possible when the alkyl iodide below undergoes E2 elimination? How many distinct alkene products are possible when the alkyl iodide below undergoes E2 elimination? A) 1 B) 2 C) 3 D) 4 E) 5


A) 1
B) 2
C) 3
D) 4
E) 5

F) A) and B)
G) None of the above

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Geraniol is a fragrant alcohol found in roses.It is biologically synthesized from geranyl phosphate by SN1.What is the leaving group in this reaction? Geraniol is a fragrant alcohol found in roses.It is biologically synthesized from geranyl phosphate by S<sub>N</sub>1.What is the leaving group in this reaction?

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Which of the following species is the least nucleophilic?


A) (CH3) 3CO-
B) H2O
C) (CH3) 3N
D) BF3
E) CN-

F) A) and B)
G) B) and E)

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Which of the following is classified as a vinyl halide?


A) CH3CH Which of the following is classified as a vinyl halide? A) CH<sub>3</sub>CH CHOH B) CH<sub>3</sub>CH CHCl C) CH<sub>3</sub>CH CHCH<sub>2</sub>Cl D) CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>Br E) BrCH<sub>2</sub>CH CH<sub>2</sub> CHOH
B) CH3CH Which of the following is classified as a vinyl halide? A) CH<sub>3</sub>CH CHOH B) CH<sub>3</sub>CH CHCl C) CH<sub>3</sub>CH CHCH<sub>2</sub>Cl D) CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>Br E) BrCH<sub>2</sub>CH CH<sub>2</sub> CHCl
C) CH3CH Which of the following is classified as a vinyl halide? A) CH<sub>3</sub>CH CHOH B) CH<sub>3</sub>CH CHCl C) CH<sub>3</sub>CH CHCH<sub>2</sub>Cl D) CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>Br E) BrCH<sub>2</sub>CH CH<sub>2</sub> CHCH2Cl
D) CH3CH2CH2CH2Br
E) BrCH2CH Which of the following is classified as a vinyl halide? A) CH<sub>3</sub>CH CHOH B) CH<sub>3</sub>CH CHCl C) CH<sub>3</sub>CH CHCH<sub>2</sub>Cl D) CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>Br E) BrCH<sub>2</sub>CH CH<sub>2</sub> CH2

F) A) and B)
G) B) and D)

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Draw the product of the following reaction. Draw the product of the following reaction.

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Give the major product for the following E2 reaction. Give the major product for the following E2 reaction. A) B) C) D) E) no reaction


A) Give the major product for the following E2 reaction. A) B) C) D) E) no reaction
B) Give the major product for the following E2 reaction. A) B) C) D) E) no reaction
C) Give the major product for the following E2 reaction. A) B) C) D) E) no reaction
D) Give the major product for the following E2 reaction. A) B) C) D) E) no reaction
E) no reaction

F) A) and B)
G) B) and D)

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Give the name(s) of the product(s) for the following SN2 reaction. Give the name(s) of the product(s) for the following S<sub>N</sub>2 reaction. A) (S) -2-hexanol B) (R) -2-hexanol C) (S) -3-hexanol D) (R) -3-hexanol


A) (S) -2-hexanol
B) (R) -2-hexanol
C) (S) -3-hexanol
D) (R) -3-hexanol

E) C) and D)
F) B) and D)

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Which sequence of reagents works best to convert 1-bromobutane to hexane?


A) 1) NaOCH3,CH3OH 2.NaCN 3.Na,NH3
B) 1) NaC Which sequence of reagents works best to convert 1-bromobutane to hexane? A) 1) NaOCH<sub>3</sub>,CH<sub>3</sub>OH 2.NaCN 3.Na,NH<sub>3</sub> B) 1) NaC CH 2.H<sub>2</sub> (excess) ,Pd/C C) 1) CH<sub>3</sub>CH<sub>2</sub>OH,delta 2.H<sub>2</sub> (excess) ,Pd/C D) 1) NaCN 2.BH<sub>3</sub>*THF 3.HO<sup>-</sup>,H<sub>2</sub>O<sub>2</sub> E) 1) NaC CCH<sub>2</sub>CH<sub>3</sub> 2.Na,NH<sub>3</sub> CH 2.H2 (excess) ,Pd/C
C) 1) CH3CH2OH,delta 2.H2 (excess) ,Pd/C
D) 1) NaCN 2.BH3*THF 3.HO-,H2O2
E) 1) NaC Which sequence of reagents works best to convert 1-bromobutane to hexane? A) 1) NaOCH<sub>3</sub>,CH<sub>3</sub>OH 2.NaCN 3.Na,NH<sub>3</sub> B) 1) NaC CH 2.H<sub>2</sub> (excess) ,Pd/C C) 1) CH<sub>3</sub>CH<sub>2</sub>OH,delta 2.H<sub>2</sub> (excess) ,Pd/C D) 1) NaCN 2.BH<sub>3</sub>*THF 3.HO<sup>-</sup>,H<sub>2</sub>O<sub>2</sub> E) 1) NaC CCH<sub>2</sub>CH<sub>3</sub> 2.Na,NH<sub>3</sub> CCH2CH3 2.Na,NH3

F) A) and C)
G) None of the above

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The rate of an SN1 reaction is fastest in


A) 100% ethanol.
B) 80% ethanol and 20% water.
C) 50% ethanol and 50% water.
D) 25% ethanol and 75% water.
E) 100% water.

F) None of the above
G) B) and C)

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Give the mechanism of the reaction shown below. Give the mechanism of the reaction shown below.

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Provide the structure of the major organic product of the following reaction. Provide the structure of the major organic product of the following reaction.

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Why are vinylic halides unreactive in both SN2 and SN1 reactions?

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Vinylic halides do not undergo SN2 reacti...

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Which of the following best describes the carbon-chlorine bond of an alkyl chloride?


A) nonpolar; no dipole
B) polar; δ+ at carbon and δ- at chlorine
C) polar; δ- at carbon and δ+ at chlorine
D) ionic
E) none of the above

F) B) and D)
G) C) and D)

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