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C8-Assigned homework from chapter 8-Name:

1. What is the major product for the following reaction? HBr

2. What is the major product for the following reaction?

HCl

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

HBr

4. What product would you expect from addition of deuterium chloride to 2-cyclohexyl4-methyl-2-pentene?

5. Addition of hydrogen chloride to the following molecule would produce:

6. Consider the addition of HCl to 3-methyl-1butene. The major product of the reaction would be:

7. What is the major product of the following reaction sequence?

1. HI 2. t-BuOK, t-BuOH

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C8-Assigned homework from chapter 8-Name: 8. What is the major product of the following reaction sequence?

1. HCl 2. t-BuOK, t-BuOH 9. A synthetic strategy for converting trans-2butene into pure cis-2-butene would consist of which of the following?

10. The reaction of BrCl (bromine monochloride) with 1-methylcyclopentene will produce as the predominant product:

11. What is the major product of the following reaction sequence? 1. Br2 , H2O 2. NaH, THF

12. An optically active compound, A, with the molecular formula C7H12 reacts with cold dilute KMnO4 and gives IR absorption at about 3300 cm-1. On catalytic hydrogenation, A is converted to B (C7H16) and B is also optically active. Which is a possible structure for A? 13. What is the major product of the following reaction sequence? Br

1. EtOH, EtONa 2a. OsO 4, pyridine 2b. H 2O, NaHSO3

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Hint: NaH is a strong base, makes a strong nucleophile from -OH

C8-Assigned homework from chapter 8-Name: 14. Determine a possible structure for an alkene, X, formula C9H14, on the basis of the following information: X adds one mole of hydrogen on catalytic hydrogenation. On treatment with hot basic KMnO4 followed by acidification, X yields the following dicarboxylic acid.

[Hint: Hot basic KMnO4 convert an alkene with hydrogens into a carboxylic acid and without hydrogen into a ketone]

15. Which of the following reactions of cyclobutene would yield a meso product?

A) Reaction with H3O+, H2O B) Reaction with Br2, CCl4 C) Reaction with Cl2, CCl4 D) Reaction with D2, Pt E) Reaction with hot, alkaline KMnO4, followed by acid workup

16. One mole of an optically active compound, X, with the molecular formula C6H8 reacts with three moles of hydrogen in the presence of a catalyst to yield an optically inactive product that cannot be resolved. X also exhibits IR absorption at approximately 3300 cm-1. Which is a possible structure for X? 17. Deduce the structure of an unknown compound A, C8H14, from the following data. Briefly, but clearly explain your rationale. A decolorizes Br2/CCl4, and upon reaction with excess H2/Ni, affords 1-ethyl-2methylcyclopentane. When A is subjected to ozonolysis, the following product is obtained.

A) (E)-4-hexen-1-yne B) (Z)-4-hexen-1-yne C) (E)-2-hexen-4-yne D) 2-methyl-1-penten-3-yne E) 3-methyl-1-penten-4-yne

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C8-Assigned homework from chapter 8-Name: 18. What are possible products for the following reaction?

HBr

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