Quiz 7.1 Alkene Additions and Hydrohalogenations7+Quiz...Quiz 7.4 – Adding Halogens to Alkenes 1....

Ch. 7 – Alkenes and Alkynes DAT Organic Chemistry Outline

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Quiz 7.1 – Alkene Additions and Hydrohalogenations

1. Which is the most stable carbocation?

2. Which of the following is an intermediate in the Markovnikov addition of HBr to 2-

methylcyclohexene?

3. What is the major product of the following reaction?

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Quiz 7.1 – Alkene Additions and Hydrohalogenations (Continued)


Quiz 7.2 – Carbocation Rearrangements

1. Draw the major organic product generated by the following reaction:

2. What is the major product of the Markovknikov addition of HBr to the following

molecule?



Quiz 7.3 – How to add –OH and –OR to Alkenes

1. Which of the following would produce a secondary alcohol when reacted with

oxymercuration-demercuration conditions?

2. Which best describes the regioselectivity and stereospecificity in the oxymercuration-

demercuration of an alkene?

A. Markovnikov orientation with syn-addition

B. Markovnikov orientation with anti-addition

C. anti-Markovnikov orientation with syn-addition

D. anti-Markovnikov orientation with anti-addition

E. Markonikov orientation with both syn- and anti-addition

3. Which of the following reactions will lead to the formation of methoxycyclopentane as

the major product?




Quiz 7.3 – How to add –OH and –OR to Alkenes (Continued)

4. Which set of reagents will accomplish the following transformation?

A. BH3-THF, then H2O2/NaOH

B. OsO4, t-BuOOH

C. H3O+/CH3OH

D. Hg(OAc)2/H2O, then NaBH4

E. m-CPBA, then NaOCH3




Quiz 7.4 – Adding Halogens to Alkenes

1. What are the major products of the following reactions?



4. Challenge Question: Draw the product(s) of the following reaction:



Quiz 7.5 – Anti-Markovnikov Alkene Additions

1. Predict the major organic product of the following reaction:

2. What compound is the expected product upon hydrohalogenation of

2-methylpent-2-ene with peroxide and HBr?

3. What is the major organic product of the following reaction?



Quiz 7.6 – Epoxides and Dihydroxylations

1. Which set of reagents will accomplish the following transformation?

A. 1. H2O2 2. CH3OH

B. 1. (CH3)2S=CH2 2. CH3O–Na+

C. 1. Hg(OAc)2/NaOH, H2O2 2. CH3Li

D. 1. OsO4 2. CH3MgBr

E. 1. mCPBA 2. CH3MgBr

2. What are the major products of the following reactions?

3. Predict the major product of the following reaction:




Quiz 7.6 – Epoxides and Dihydroxylations (Continued)

4. What reaction sequence is required to yield the product below?

A. II → IV → III

B. II → I

C. IV → III

D. III → IV

E. II → IV → I

5. Which starting material gives the product in the reaction sequence below?



Quiz 7.7 – Ozonolysis

1. Please identify the missing reactant:

2. What is the structure of a compound, which has a molecular formula of C6H10, which

upon ozonolysis and subsequent treatment with zinc and water, gives the following

product?




Quiz 7.7 – Ozonolysis (Continued)

3. What is the major organic product of the following reaction?

4. What is/are the product(s) of the following reaction?



Quiz 7.8 – Catalytic Hydrogenation

1. What are the products of the following reactions?

2. Which set of reagents will accomplish the following chemical transformation?

A. (1) NaNH2, (2) CH3Br, (3) H3O+

B. H2, Lindlar

C. Li, NH3

D. (1) LiAlH4, (2) H3O+

E. HgSO4, H2SO4

3. Which reagent is best for preparing (Z)-4-methyl-2-hexene from 4-methyl-2-hexyne?

A. H2, Pd/C

B. Na/NH3

C. H2NNH2, NaOH

D. Zn(Hg) / HCl

E. H2, Lindlar’s catalyst (Pd/CaCO3)



Quiz 7.9 – Alkyne Addition Reactions

1. Predict the products of the following reactions:




Quiz 7.10 – Alkyne Hydration and Alkylation



Quiz 7.1 Alkene Additions and Hydrohalogenations7+Quiz...Quiz 7.4 – Adding Halogens to Alkenes 1....

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