Chapter 8 Homework PDF

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CH235-2E ORGANIC CHEMISTRY I Quiz 8 GENERAL 1. What is the IUPAC name of the following compound?

a. b. c. d.

(R)-1-chloro-3-methyl-2-cyclohexene (S)-1-chloro-3-methyl-2-cyclohexene (R)-3-chloro-1-methylcyclohexene (S)-3-chloro-1-methylcyclohexene

2. What is the IUPAC name of the following compound?

a. b. c. d.

(R)-2-bromo-2-vinylpentane (S)-2-bromo-2-vinylpentane (S)-3-bromo-3-propyl-1-butene (R)-3-bromo-3-methyl-1-hexene

3. What is the correct assignment of the names of the following compounds? 1. 2. 3. a. b. c. d.

CH3Cl CH2Cl2 CHCl3 1 = methyl chloride; 2 = chloroform; 3 = methylene chloride 1 = trichlor; 2 = chloroform; 3 = methylene chloride 1 = methyl chloride; 2 = methylene chloride; 3 = chloroform 1 = chloroform; 2 = methylene chloride; 3 = trichlor

4-5. Provide the IUPAC name of the following compound.

6. Provide the IUPAC name of the following compound (shown as a Fischer projection).

7. Which of the following has the list of compounds in the correct order of decreasing boiling point (higher boiling point > lower boiling point)? a. chloromethane > chloroethane > 2-chloropropane > 2-chloro-2-methylpropane b. 2-chloro-2-methylpropane > 2-chloropropane > chloroethane > chloromethane c. chloroethane > chloromethane > 2-chloro-2-methylpropane > 2-chloropropane d. chloromethane > 2-chloro-2-methylpropane > 2-chloropropane > chloroethane

8. Which of the following bonds has the lowest bond dissociation enthalpy? a. CH b. CF c. CBr d. CI PREPARATION METHOD I 9. Which of the following alkenes undergoes allylic bromination to form a single monobrominated product?

a. b. c. d.

1 2 3 4

10. What is the major product formed upon radical bromination of (S) 3-methylhexane? a. (S) 3-bromo-3-methylhexane b. (R) 3-bromo-3-methylhexane c. a mixture of (R) and (S) 3-bromo-3-methylhexane d. (3R) 1-bromo-3-methylhexane 11. What is the major product obtained from the reaction of 2-methyl-2-butene with hydrogen bromide in the presence of peroxides? a. 2,3-dibromo-2-methylbutane b. 2-bromo-3-methylbutane c. 2-bromo-2-methylbutane d. (E)-1-bromo-2-methyl-2-butene 12. Which of the following statements is not true? a. Bromine radicals add to the least substituted end of a carbon-carbon double bond of an alkene. b. The major anti-Markovnikov product obtained upon addition of HBr to alkenes in the presence of a peroxide is formed in a radical termination step. c. Two radicals combine in radical termination steps. d. Alkoxy radicals remove a hydrogen atom from HBr to give an alcohol and a bromine atom.

13. What is the major organic product obtained from the following reaction?

a. b. c. d.

1 2 3 4

14. What are the major products formed upon treatment of (E) 3-methyl-2-hexene with HBr in the presence of peroxides? 1. 2. 3. 4. a. b. c. d.

(S,S) 2-bromo-3-methylhexane (S,R) 2-bromo-2-methylhexane (R,S) 2-bromo-2-methylhexane (R,R) 2-bromo-2-methylhexane only 1 and 2 only 1 and 4 only 2 and 3 a mixture of 1, 2, 3, and 4

15.What are the major products formed upon treatment of (E) 3-methyl-2-hexene with HBr in the absence of peroxides? 1. 2. 3. a. b. c. d.

(S) 3-bromo-3-methylhexane (R) 3-bromo-2-methylhexane 2-bromo-3-methylhexane only 1 only 2 a mixture of 1 and 2 only 3

16. Which of the following accounts for the anti-Markovnikov regiochemistry of the reaction of an alkene with HBr in the presence of peroxides? a. the alkene reacts with HBr to give a carbocation b. the alkene reacts with a bromine atom to give a radical c. the alkene reacts with a hydrogen atom to give a radical d. the alkene reacts with peroxide to five an allylic radical 17.What is the major organic product obtained from the following reaction?

18. What is the major organic product obtained from the following reaction?

PREPARATION METHOD II 19. What is the major organic product obtained from the following reaction?

a. b. c. d.

1 2 3 4

20. What is the geometry of the central carbon atom of a tert-butyl radical? a. tetrahedral b. trigonal planar c. trigonal pyramidal d. square planar 21. What is the correct order of stability of the following radicals (more stable > less stable)?

a. b. c. d.

1>2>3 2>1>3 2>3>1 3>2>1

22. What is the characteristic of a radical chain initiation step? a. radicals are formed b. substitution products are formed c. a radical reacts with a molecule to give a new radical and a new molecule d. two radicals combine to give a molecule 23. What is the characteristic of a radical chain propagation step? a. radicals are formed b. byproducts are formed c. a radical reacts with a molecule to give a new radical and a new molecule d. two radicals combine to give a molecule

24. What is the characteristic of a radical chain termination step? a. radicals are formed b. substitution products are formed c. a radical reacts with a molecule to give a new radical and a new molecule d. two radicals combine to give a molecule PREPARATION METHOD III 25. What are the major organic products obtained from the following reaction?

a. b. c. d.

1 and 2 3 and 4 1 and 3 2 and 4

26. What type of reactive intermediate is formed in the reaction of propene with N-bromosuccinimide to give 3-bromo-1-propene? a. allylic carbocation b. allylic carbanion c. allylic radical d. cyclic bromonium ion 27. What type of reactive intermediate is formed upon irradiation of a solution of toluene (Ph-CH3) and bromine? a. benzylic carbocation b. benzylic carbanion c. benzylic radical d. cyclic bromonium ion 28. Which of the following is an accurate statement of Hammond's postulate? a. the transition state of an exothermic reaction will resemble the starting materials (reactants) more than the product b. the transition state of an exothermic reaction will resemble the products more than the starting materials (reactants) c. the transition state of an endothermic reaction will resemble the starting materials (reactants) more than the product d. the difference in energy between the starting materials (reactants) and transition state controls the rate of a reaction 29. What is the major product of autooxidation of cyclohexene?

a. b. c. d.

1 2 3 4

30. What is the structure of all of the monobrominated products, including regioismers and stereoisomers, obtained from the following reaction?

31. What is the major organic product obtained from the following reaction?

PREPARATION METHOD IIIV 32. Complete the following reactions...