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Chapter 4

1. What is the IUPAC name for the following compound?

A) B) C) Ans:

7,7 diethyl-5-isopropyl-3,4-dimethyldecane 7,7-diethyl-5-isopropyl-2,3-dimethyldecane 7,7-diethyl-4-isopropyl-2,3-dimethyldecane B

2. Give the IUPAC name for the following compound.

A) 7,7-diethyl-2,4,5-trimethylnonane B) 7-ethyl-2,4,5-trimethyloctane Ans: A

C)

6-ethyl-2,4,5-trimethyloctane

3. Give the IUPAC name for the following compound.

A) 4,4-diethyl-2,3,6-trimethylnonane B) 5,5-diethyl-4,7,8-trimethylnonane Ans: C

C)

5,5-diethyl-2,3,6-trimethylnonane

4. Give the IUPAC name for the following compound.

A) 2,5-dimethyl-3-t-butylheptane B) 2,5-dimethyl-4-t-butylhexane Ans: C

C)

2,5-dimethyl-4-t-butylheptane

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A) 5-sec-butyl-2.5. Give the IUPAC name for the following compound.4-dimethylnonane B) 6-sec-butyl-2. A) B) C) Ans: 1-sec-butyl-4-isopropyl-2-methylcycloheptane 1-sec-butyl-4-isopropyl-2-methylcyclohexane 1-sec-butyl-3-isopropyl-3-methylcyclohexane B Page 2 .4-dimethyldecane Ans: C C) 6-sec-butyl-3. Give the IUPAC name for the following compound.5-dimethyldecane 7. Give the IUPAC name for the following compound. H H3C H H CH3 A) 2-methyl-4-isopropylheptane B) 2-methyl-4-isopropyloctane Ans: A C) 3-methyl-5-isopropylhexane 8. Give the IUPAC name for the following compound. A) 7-ethyl-6-isobutyl-3-methylundecane C) B) 7-ethyl-6-isobutyl-3-methylnonane Ans: C 7-ethyl-6-isobutyl-3-methyldecane 6.

7-dimethyl-7-propyluncedecane 4-isobutyl-2. H H H A) 4-ethyl-5-isopropylnonane B) 5-ethyl-4-isopropyloctane Ans: C C) 5-ethyl-4-isopropylnonane 10.7-diethyl-2.7-diethyl-2. Give the IUPAC name for the following compound.3-dimethyldecane 5-sec-butyl-7.3-dimethyldecane 4-sec-butyl-6.6-diethyl-2.5-dimethyl-5-propylnonane 5-isobutyl-2. Give the IUPAC name for the following compound. Give the IUPAC name for the following compound. A) 4-isobutylyl-2-methylhexane B) 4-isopropyl-3-methylheptane Ans: B C) 4-isopropyl-2-methylheptane Page 3 . A) B) C) Ans: 5-sec-butyl-7.6-dimethyl-6-propyldecane C 12.9. Give the IUPAC name for the following compound. A) B) C) Ans: 6-isobutyl-3.3-dimethylundedecane A 11.

The preferred conformation of cis-3-t-butyl-1-methyl-cyclohexane is one in which: A) the t-butyl group is axial and the methyl is equatorial.6-trimethylnonane Ans: B C) 4. A) 5. C) both groups are axial.4-trimethyloctane 15.4-trimethylnonane Ans: A C) 2.3.13.5-diethyl-3. B) the methyl group is axial and the t-butyl group is equatorial.3.3.5-diethyl-2. Ans: D 16. A) 3.4-diethyl-2. Give the IUPAC name for the following compound.5-diethyl-2. Which represents the ring-flipped conformer of a? A) A Ans: D B) B C) C D) D E) E Page 4 .5-trimethylnonane B) 2.3.3.5-diethyl-3.6-trimethylnonane 14. D) both groups are equatorial.6-trimethyldecane B) 5.4.6-diethyl-4. Give the IUPAC name for the following compound. E) None of the choices are correct.

17. Which of the following structures represents the most stable form of 1-isopropyl-2-methylcyclohexane? A) A Ans: D B) B C) C D) D E) E Page 5 . Consider the molecule cis-1-ethyl-3-isopropylcyclohexane. Which is the overall most-stable conformer? A) A Ans: C B) B C) C D) D E) E 18.

A) A Ans: B B) B C) C D) D E) E 20. A) A<B<C Ans: A B) B<A<C C) C<A<B D) A<C<B E) C<B<A 21. 3-cyclohexane diol.19. Which conformation is the most stable? A) A Ans: C B) B C) C Page 6 . Select the most stable conformer of cis-1. Rank the indicated conformations in order of decreasing stability.

22. rank them in order of increasing stability. Given the three Newman projections drawn below. Rank the following conformations in order of increasing energy. A) B<A<C Ans: D B) C<A<B C) C<B<A D) B<C<A E) A<C<B 24. A) C < B < A B Ans: A B) B < A < C C) B < C < A D) A < B < C E) C < A < Page 7 .2-dibromoethane is the most stable? H H H H A Br Br H Br H B H Br H H Br C H H H H D H H H Br Br Br A) A Ans: B B) B C) C D) D 23. Which of the following conformations of 1.

Assuming that the size of substituents is H<CH3<I. which of the following conformations is the most stable? CH3 A H3 C H H I CH3 D H H3 C H H E H CH3 H I H B H I CH3 I H H CH3 CH3 H C H I H CH3 H CH3 A) A Ans: C B) B C) C D) D E) E 26.25. Which of the following two conformers is higher in energy? A) A Ans: B B) B Page 8 .

Which letter(s) on the graph correspond(s) to this Newman Projection? A) A and G Ans: D B) B and F C) C and E D) D 28. The graph below shows the energy changes that occur during rotation around the C–C bond indicated in compound a.27. Consider rotation about the indicated bond in the molecule below. Which Newman Projection best represents the most stable conformer of the molecule during rotation about the indicated bond? A) A Ans: A B) B C) C Page 9 .

They are not isomers. they are different compounds. They are stereoisomers. A is the most stable and C is the least stable. How are the molecules below related to each other? A) B) C) D) E) Ans: They are constitutional isomers. They are not isomers. They are resonance structures. B is the most stable and C is the least stable. They are identical. Which statement about the following conformers of the same compound is true? A) B) C) D) E) Ans: B is the most stable and A is the least stable. They are stereoisomers. They are identical. A Page 10 .29. E 30. A is the most stable and B is the least stable. They are resonance structures. they are different compounds. C is the most stable and A is the least stable. C 31. How are the molecules below related to each other? A) B) C) D) E) Ans: They are constitutional isomers.

They are not isomers. They are resonance structures. How are the molecules below related to each other? A) B) C) D) E) Ans: They are constitutional isomers. They are identical. B 33. They are not isomers. they are different compounds. D Page 11 . they are different compounds. They are stereoisomers. They are resonance structures.32. How are the molecules below related to each other? A) B) C) D) E) Ans: They are constitutional isomers. they are different compounds. They are identical. They are not isomers. They are stereoisomers. They are identical. They are stereoisomers. They are resonance structures. How are the molecules below related to each other? A) B) C) D) E) Ans: They are constitutional isomers. A 34.

How are the molecules below related to each other? A) B) C) D) E) Ans: They are constitutional isomers. Ca is quaternary. Ca is quaternary. they are different compounds. Which of the following statements is (are) true about the following compound? A) B) C) D) E) Ans: Ca and Cd are 1° carbons. Ce and Ca are 2° carbons. They are resonance structures. Cc is primary.35. Cb is tertiary. They are identical. and Cb is tertiary. They are stereoisomers. Cb and Cc are 3° carbons. E 37. They are not isomers. E Page 12 . Cc is primary. C 36. (Ca and Cd are 1° carbons) and (Cb and Cc are 3° carbons). Which of the following statements is (are) true about compound B below? Ca Cb B Cc A) B) C) D) E) Ans: Ca and Cb are quaternary. (Cb and Cc are 3° carbons) and (Ce and Ca are 2° carbons).

B) Both groups are axial. What is the relative position of the substituents A and B to each other in the following conformation? A) Anti Ans: D B) Eclipsed C) Syn D) Gauche 41.38.3-dimethylbutane? H H3C H3C CH3 A CH3 H H H CH3 B CH3 CH3 CH3 H3C H CH3 C CH3 H CH3 H H3C CH3 D CH3 H CH3 A) A Ans: C B) B C) C D) D Page 13 . Which of the following Newman projections represents the most stable conformation of 2. A) The isopropyl group is axial and the ethyl group is equatorial. D) The isopropyl group is equatorial and the ethyl group is axial. E) There is no way to predict for this molecule. C) Both groups are equatorial. Predict the most stable conformation of cis-1-isopropyl-4-ethylcyclohexane. Which of the following equations is correct for the combustion of cyclohexane? A) B) C) D) E) Ans: B 40. Ans: D 39.

H H A) B) C) D) E) Ans: A has more torsional strain. Which of the following statements best explains the reason for the relative stabilities of the two conformers shown below? H H CH3 A. Which of the following cyclohexane derivatives is most stable? A B C D A) A Ans: A B) B C) C D) D Page 14 . B has more steric strain. A and B have the same torsional strain.42. A and B have similar steric strain. B has more torsional strain. E Challenge Questions 43. B has more torsional strain. A has more steric strain. A and B have the same steric strain. H H H H H H A) B) C) D) E) Ans: 4-isobutyl-2-ethyl-1-isopropylcyclohexane 4-sec-butyl-2-ethyl-1-isopropylsyclobutane 4-sec-butyl-2-ethyl-1-isopropylcyclohexane 2-ethyl-4-isobutyl-1-isopropylcyclohexane 1-isopropyl-2-ethyl-4-secbutylcyclobutane C 44. CH3 CH3 H H3C CH3 H H3C B. Give the IUPAC name for the following compound.

In the 1995 synthesis by E. (3Z)-Dactomeleyne has been isolated from the digestive glands of the sea hare Aplysia dactylomela.45. HO 1 2 3 4 O O O NHBoc 5 (intermediate for Cryptophycin C) HO H O H BocHN H A O O HO H O H H O BocHN H C HO O H H BocHN H B O O H O H A) A Ans: A B) B C) C Page 15 . Identify the most stable Newman projection looking down the C2-C3 bond. Cryptophycin C is a marine natural product with anti-cancer activity. the compound below undergoes a reduction reaction to produce one of the late stage intermediates. Identify a possible product from this reaction. Cl O OH Cl O OH O Br O Br CO2CH3 ? COCl Cl O O O Br Cl CO2CH3 O OH O Br CO2CH3 Cl O OH O Br OH A B C D A) A Ans: D B) B C) C D) D 46. An intermediate in its synthesis is shown below. Lee and co-workers.

iii) identical. iv) stereoisomer i) Stereoisomer. ii) stereoisomer. iv) identical C Page 16 . ii) constitutional isomer. How is each molecule (i-iv) related to compound A? OH OMe MeO O NH2 Compound A OH OMe HO NH2 O OMe MeO O OH OH OMe OMe NH2 OH MeO O H OH NH2 OH HO MeO O OMe OH H NH2 i ii iii iv A) B) C) D) Ans: i) Constitutional isomer. iii) identical. iv) stereoisomer i) identical. ii) identical. iii) identical.47. iv) stereoisomer i) stereoisomer. ii) constitutional isomer. iii) constitutional isomer.