CHEM222 Final - 2

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53. The major organic product generated in the reaction below is (A) 2-methylpentan-2-ol (B) 2-methylpentan-3-ol (C) 1,1-dimethylbutan-2-ol (D) 2-boro-3-hydroxypentane

(B) 2-methylpentan-3-ol

33. The major organic product(s) in the reaction below is (A) 2-ethyl-1-methylbutan-1-ol (B) 3-ethylpentan-2-ol (C) 2-ethyl-1-methylpent-2-acetate (D) 1-boro-3-ethylpentane

(B) 3-ethylpentan-2-ol

20. The major product generated in the reaction below is (A) pentan-1-ol (B) pentan-2-ol

(B) pentan-2-ol

57. Provide the major organic product of the reaction shown below. (A) 3-cyclopentyl-2-bromopropane (B) 3-cyclopentyl-1-bromopentane (C) 1-bromopropylcyclopentane (D) 3-cyclopentyl-2-peroxypropane

8. The major organic product generated in the reaction below is (A) 1-chloro-2-methylcyclohexane (B) 1-chloro-2-methylcyclohexene (C) 1-chloro-1-methylcyclohexane (D) 1-chloro-1-methylcyclohexene

36. The product in the reaction below is (A) 2,2-dichloro-3-methylpentane (B) 3,3-dichloro-2-methylpentane (C) 2,3-dichloro-3-methylpentane (D) 1,3-dichloropentane

42. The products of the reaction below are (A) 3,4-epoxy-3-methylpentane + propanoic acid (B) 3,4-epoxy-3-methylpentane + ethanoic acid (C) 2,3-epoxy 3-methylpentane + propanoic acid (D) 2,3-epoxy-3-methylpentane + ethanoic acid

11. The major organic product generated in the reaction below is (methyl shift) (A) 2,3-dimethyl-3-chlorobutane (B) 2-chloro-3,3-dimethylbutane (C) 2-chloro-2,3-dimethylbutane (D) 1-chloro-3,3-dimethylbutane

27. The major organic product(s) in the reaction below is (hydride shift) (A) 3-ethyl-1-methoxypentane (B) 3-ethyl-2-methoxypentane (C) 3-ethyl-3-methoxypentane (D) 3-ethyl-3-methoxypentene

23. The major product of the reaction below is (hydride shift) (A) 3-ethylpentan-1-ol (B) 3-ethyl-pentan-2-ol (C) 3-ethyl-pentan-3-ol (D) 3-ethylpenten-1-ol

54. Provide the major organic product in the reaction below. (A) 3-ethylpentan-3-ol (B) 3-ethylpentan-2-ol (C) 3-ethylpentan-1-ol (D) 2-boro-3-ethylpentan-1-ol

32. Provide the structure of the major organic product of the following reaction. (A) 2,3-dimethylbutan-2-ol (B) 3-methylbutan-3-ol (C) 3-methylbutan-2-ol (D) 3-methyl butyl-2-acetate

19. The major product of the reaction below is (A)2-methylpentan-3-ol (B) 2-ethylbutan-2-ol (C) 3-methylpentan-3-ol (D) 3-methylpentan-2-ol

10. What is the hybridization of the carbon atoms numbered 1 and 2 respectively in the following structure? (A) sp2, sp2 (B) sp, sp (C) sp2, sp (D) sp, sp2

29. The product of the reaction below is (A) 1-cyclohexylpropan-1-ol (B) 1-cyclohexylpropan-2-acetate (C) 3-cyclohexylpropanol (D) 1-propylcyclohexanol

(D) 1-propylcyclohexanol

34. The major organic product of the following reaction is (A) 2-methyl-3-methoxybutene (B) 3-methyl-2-fluorobutane (C) 2-methyl-2-methoxybutane (D) 3-methyl-2-methoxybutane

(D) 3-methyl-2-methoxybutane

22. The major product generated in the reaction below is (hydride shift) (A) 3-methylpentan-1-ol (B) 3-methylpentan-2-ol (C) 2-methylpentan-2-ol (D) 3-methylpentan-3-ol

(D) 3-methylpentan-3-ol

16. Give the best product for the reaction.

28. Identify the most stable carbocation.

7. How many carbon atoms are present in the molecule shown? A) 6 B) 8 C) 10 D) 11 (also work out # of H's; degree of unsaturation)

C) 10 # of H's -18 degree of unsaturation - 2

2. How many asymmetric carbon atoms are present in the molecule shown? A) 0 B) 1 C) 2 D) 3

C) 2

17. What is the name of the major organic product of the following reaction? (methyl shift) A) 3,3-dimethylbutan-1-ol B) 3,3-dimethylbutan-2-ol C) 2,3-dimethylbutan-2-ol D) 2,3-dimethylbutan-1-ol E) 4-methylpentan-2-ol

C) 2,3-dimethylbutan-2-ol

12. How many distinct internal alkynes exist with a molecular formula of C6H10? A) 1 B) 2 C) 3 D) 4 E) 5

C) 3

24. Give the best reagents for the reaction. A) H2, Pd B) 1. NaBH4, 2. H3O+ C) H2, Lindlar catalyst D) Na, NH3

C) H2, Lindlar catalyst

12. Which of the following is the most stable conformation of bromocyclohexane? A) I B) II C) III D) V

C) III

18. What is the major product of the following reaction? A) I B) II C) III D) IV E) V

C) III

3. Which of the following pairs are resonance structures? A) I B) II C) III D) IV E) V

C) III

44. Which of the following reagents best facilitates the reaction shown below? A) I B) II C) III D) IV E) V

C) III

13. In the structure below, the sigma bond of the carbonyl is formed from the overlap of a(n) ________ atomic orbital of carbon and a(n) ________ atomic orbital of oxygen. A) sp, sp2 B) sp3, sp2 C) sp2, sp2 D) p, p

C) sp2, sp2

21. Identify the true statements in the mechanism for the addition of water to an alkene. A) The addition of the electrophile is a slow step. B) The addition of the nucleophile is a fast step. C) A carbocation is formed as an intermediate. D) Water abstracts the extra proton from the protonated alcohol. E) All of the above.

E) All of the above.

22. Provide the proper IUPAC name for the alkene shown below (include E or Z).

E-3,4-dimethylhept-3-ene

25. Provide the systematic name of the compound shown below. Include the E or Z designator if necessary

E-4-ethylnon-3-ene

13. Provide the systematic name of the compound shown.

E-5-methylhept-5-en-1-yne

31. Name the alkene shown. Be sure to include the appropriate E or Z label necessary.

E1-bromo-4-chlorohept-3-ene

5. Is the molecule shown below chiral or achiral?

achiral

7. Is the molecule shown below chiral or achiral?

achiral

6. Is the molecule shown below chiral or achiral?

chiral

. Structures which differ only in rotations about a single bond are called ________.

confomers

17. Are the two compounds shown below best described as cis-trans isomers, constitutional isomers, or not isomeric?

constitutional isomers

18. Are the two compounds shown below best described as cis-trans isomers, constitutional isomers, or not isomeric?

constitutional isomers

48. Give the structure of the alkene which would yield the following products upon ozonolysis-reduction. CH3CH2CH2CH2CHO + H2C=O

hex-1-ene

12. What ONE alkene should be used to complete the synthesis reaction below? Give a reason.

hex-3-ene; symmetrical

13. What ONE alkene should be used to synthesize 2-bromopentane? Give a reason.

pent-1-ene

16. Give the IUPAC name for HCCCH2CH2CH3.

pent-1-yne

45. Provide the organic products of the following.

propynol

6. Do the following structures represent different compounds or resonance contributors?

resonance contributors

1. Which of the following alkenes reacts with HCl at (i) the slowest rate? (ii) the fastest rate?

slowest-A, fastest-E

10. The major product of the reaction below is (A) 3-chloro-3-methylpentane (B) 3-methyl-3-chloropentane (C) 2-chloro-2-ethylbutane (D) 3-chloro-3,4-dimethylpentane

(A) 3-chloro-3-methylpentane

40. The major organic product generated in the reaction below is (A) 1-methylhydroxy-1-chlorocyclohexane (B) 1-chloromethyl cyclohexanol (C) 1-chloro-1-cyclohexyl ethanol (D) cyclohexyl chloromethanol

(B) 1-chloromethyl cyclohexanol

30. The organic product generated in the reaction below is (A) 1-methylcyclopentan-2-ol (B) 1-methylcyclopentanol (C) 1-acetic-2-methylcyclopentane (D) 2-methylcyclopentanol

(B) 1-methylcyclopentanol

4. The major organic product of the following reaction is (A) 3-bromo-2-methylpentane (B) 2-bromo-2-methylpentane (C) 1-bromo-1,1-dimethylbutane (D) 3-bromo-4,4-dimethylbutane

(B) 2-bromo-2-methylpentane

17. Give the IUPAC name for BrCH2CH2CCCH2CH3.

1-bromohex-3-yne

5. What is the approximate value of any H-C-C bond angle in H2C=CHCCl3?

120 degrees

3. The molecule shown below contains ________ sigma bonds and ________ pi bonds.

14 sigma, 3 pi

1. What is the approximate value of the CCC bond angle in CH3C≡CCH3?

180 degrees

4. The molecule shown below contains ________ pi bonds and ________ sigma bonds.

2 pi, 13 sigma

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

2,2-dibromopropylcyclopentane

11. Provide the systematic name of the alkene below.

2-ethylhex-1-ene

12. Name the compound shown below.

2-propylcyclopenta-1,3-diene

18. Provide the IUPAC name of the compound shown.

5,6,6-trimethylhept-1-yne

6. Determine the most stable conformer of butane from the conformers below

15. Give the best product for the reaction.

18. Give the best product for the reaction.

4. Which Newman projection shows the most stable conformation of the following compound?

7. Give the best stable product for the reaction.

8. Which of the following is an sp2 hybridized carbon?

3. How many asymmetric carbon atoms are present in the molecule shown? A) 0 B) 1 C) 2 D) 3

A) 0

4. How many asymmetric carbon atoms are present in the molecule shown? A) 0 B) 1 C) 2 D) 3

A) 0

51. What reagents can best be used to accomplish the following transformation? A) 1. BH3∙THF 2. HO-, H2O2 B) H+, H2O C) 1. Hg(OAc)2, H2O/THF 2. NaBH4 D) 1. Hg(O2CCF3)2, CH3OH 2. NaBH4

A) 1. BH3∙THF 2. HO-, H2O2

9. What is the IUPAC name for the following compound? A) 2-methylbut-1-ene B) isopentene C) 2-methybutene D) 2-ethylpropene E) 3-methylbut-3-ene

A) 2-methylbut-1-ene

19. Name the structure. A) 7-chloro-3-ethyl-4-methylhept-3-ene B) 1-chloro-5-ethyl-4-methylhept-3-ene C) 1-chloro-3-pentenylpent-2-ene D) cis-7-chloro-3-ethyl-4-methylhept-3-ene

A) 7-chloro-3-ethyl-4-methylhept-3-ene

1. Which of the following statements correctly describes the general reactivity of alkynes? A) An alkyne is an electron-rich molecule and therefore reacts as a nucleophile. B) The σ bonds of alkynes are higher in energy than the π bonds and are thus more reactive. C) Alkynes fail to undergo nucleophilic addition reactions, react as electrophiles. D) Alkynes are generally more reactive than alkenes.

A) An alkyne is an electron-rich molecule and therefore reacts as a nucleophile.

28. Which of the following best describes the geometry about the carbon-carbon double bond in the alkene below? A) E B) Z C) neither E nor Z

A) E

49. What are the major organic products when the following molecule is treated with ozone, and then with Zn/H2O? A) I B) II C) III D) IV E) V

A) I

1. Which of the following structures (a-d) is another resonance structure of the following organic molecule?

8. Give the best stable product for the reaction.

1. How many asymmetric carbon atoms are present in the molecule shown? A) 0 B) 1 C) 2 D) 3

B) 1

4. How many sp hybridized carbon atoms are present in the molecule shown? A) 0 B) 1 C) 2 D) 3

B) 1

25. Give the best reagents for the reaction. A) H2O, H2SO4, HgSO4 B) 1. BH3/THF 2. HO-, H2O, H2O2 C) K2Cr2O7, H+ D) NaOCl

B) 1. BH3/THF 2. HO-, H2O, H2O2

12. Based on the structure below, what is the value for the H-N-CH3 bond angle? A) 60 B) 109 C) 90 D) 120 0

B) 109

10. What is the IUPAC name for the following compound? A) 5-methylcyclohexene B) 4-methylcyclohexene C) 1-methyl-3-cyclohexene D) 1-methyl-4-cyclohexene

B) 4-methylcyclohexene

3. Which of the following best explains the relative stabilities of the eclipsed and staggered forms of ethane? The ________ form has the most ________ strain. A) eclipsed; steric B) eclipsed; torsional C) staggered; steric D) staggered; torsional

B) eclipsed; torsional

6. Give the possibilities in structure for a compound with a formula of C6H10. A) no rings, no double bonds, no triple bonds B) one double bond, or one ring C) two rings, two double bonds, one double bond + one ring, or one triple bond D) three rings, three double bonds, two double bonds + one ring, one ring + two double bonds, one triple bond + one ring, or one double bond + one ring

C) two rings, two double bonds, one double bond + one ring, or one triple bond

8. Draw the structure of a molecule which contains only carbon and hydrogen atoms (only three of which are carbon) and in which two of the carbons are sp2 hybridized and the other is sp hybridized.

C3H4 CH2=C=CH2

2. Which species below is an electrophile?

CH3+CHCH3

56. List the following radicals in order of increasing stability (ie, from least stable to most stable). (CH3)3C∙ , CH3CH2∙ , CH3∙, (CH3)2CH∙

CH3∙, CH3CH2∙ , (CH3)2CH∙ , (CH3)3C∙

5. Give the best product for the reaction.

13. Name the structure. A) 4-chlorocyclohexene B) 1-chloro-3-cyclohexene C) 1-chloro-3-cycloheptene D) 4-chlorocycloheptene

D) 4-chlorocycloheptene

25. Which of the following is the most stable carbocation? A) I B) II C) III D) IV E) V

D) IV

39. Which reaction intermediate is formed when Br2/CCl4 reacts with cyclohexene? A) I B) II C) III D) IV E) V

D) IV

5. Which of the following is not a resonance structure of the species shown? A) I B) II C) III D) IV

D) IV

14. Which of the following alkenes yield(s) 3-bromo-3-methylpentane as the major product upon addition of HBr? A) I and II only B) III & IV only C) I, II, and III only D) all of them E) none of them

D) all of them

7. Among the butane conformers, which occur at energy minima on a graph of potential energy versus dihedral angle? A) gauche only B) eclipsed and totally eclipsed C) gauche and anti D) anti only

D) anti only

8. The structures below are: A) not isomers. B) conformational isomers. C) cis-trans isomers .D) structural isomers.

D) structural isomers

11. Which conformer is at a local energy minimum on the potential energy diagram in the chair-chair interconversion of cyclohexane? A) half-chair B) fully eclipsed C) boat D) twist-boat

D) twist-boat

7. The carbon-carbon double bond in ethene is ________ and ________ than the carbon-carbon triple bond in ethyne. A) stronger; more polar B) stronger; longer C) weaker; shorter D) weaker; longer

D) weaker; longer

14. What is the CNN bond angle in the compound shown below? A) ~180° B) ~90° C) ~110° D) ~120°

CHEM222 Final - 2

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