Chapter 7 Homework Answers PDF

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Chapter 7 Homework Answers...

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CHAPTER 7—ALKYNES MULTIPLE CHOICE

a. 110 pm

c. 135 pm d. 156 pm ANS: B 2.

What is the approximate C−C−C bond angle in propyne?

a. 90° b. 109° c. 120° d. 180° ANS: D

a. 4 b. 5 c. 6

ANS: D 4.

How many terminal alkynes are there with the molecular formula C7H12?

a. 5 b. 7 c. 8 d. 9 ANS: C 5.

Which atomic orbitals overlap to form the carbon-carbon triple bond of an alkyne?

a. 2s + 2s; sp + sp; 2p + 2p b. sp + sp; sp + sp; 2p + 2p c. sp + sp; 2p + 2p; 2p + 2p d. sp2 + sp2; sp + sp; 2p + 2p

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ANS: C 6.

Which atomic orbitals overlap to form the carbon-carbon single bond of 1-propyne?

a. 2s + sp b. sp + sp2 c. sp + sp3 d. sp2 + sp3 ANS: C

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7.

What is the smallest cycloalkyne that is stable at room temperature?

a. cyclohexyne b. cyclononyne c. cyclododecyne d. cycloeicosyne ANS: B

CH3CH2CH2−C≡C−CH(CH3)2 a. 1-isopropyl-1-pentyne

c. 6-methyl-4-heptyne d. isopropyl propyl ethyne ANS: B 9.

What is the IUPAC name of the following compound?

(CH3)2CHCH2−C≡C−CH(CH3)2 a. 2,6-dimethyl-3-heptyne b. 2,6-dimethyl-4-heptyne c. 1,1,5,5-tetramethyl-2-pentyne d. 4-nonyne ANS: A

b. 4-ethynyl-2-vinylbutane c. 3-methyl-4-vinyl-1-pentyne d. 4-ethynyl-3-methyl-1-pentyne ANS: A

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a. vinylcyclohexane b. allylcyclohexane

d. acetylcyclohexane

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ANS: C

a. (R)-4-methyl-2-hexyne

c. (R)-3-methyl-4-hexyne d. (S)-3-methyl-4-hexyne ANS: B 13.

What is the IUPAC name for the following compound?

a. (R)-3-methyl-1-penten-4-yne b. (S)-3-methyl-1-penten-4-yne c. (R)-4-methyl-4-penten-1-yne d. (S)-4-methyl-4-penten-1-yne ANS: A

a. propane b. cyclopropane c. propene

ANS: D 15.

Which of the following has the lowest pKa?

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a. butane b. 1-butene c. 1-butyne d. 2-butyne ANS: C

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16. What is the correct assignment of the acid, base, conjugate acid and conjugate base in the following equilibrium?

a. 1 = acid; 2 = base; 3 = conjugate acid; 4 = conjugate base b. 1 = acid; 2 = base; 3 = conjugate base; 4 = conjugate acid c. 1 = base; 2 = acid; 3 = conjugate acid; 4 = conjugate base d. 1 = base; 2 = acid; 3 = conjugate base; 4 = conjugate acid ANS: B 17.

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

a. cyclohexyne b. 1,3-cyclohexadiene c. cyclohexene d. 1,2-diaminocyclohexane ANS: B 18.

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

a. (E) 2-butene b. (Z) 2-butene c. 2-butyne d. 1-butyne ANS: C 19.

Which sequence of reactions can be used to convert 1-pentene to 1-pentyne

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a. Treatment with HBr; followed by treatment with NaOH b. Treatment with Br2; followed by treatment with NaNH2 c. Treatment with Br2; followed by treatment with H2SO4 d. Treatment with Br2, H2O; followed by treatment with NaOH ANS: B 20.

Which sequence of reactions can be used to convert (Z) 2-pentene to 2-pentyne

a. Treatment with Br2; followed by treatment with NaNH2 b. Treatment with Br2, H2O; followed by treatment with NaOH c. Treatment with Br2; followed by treatment with H2SO4 d. Treatment with HBr; followed by treatment with NaOH

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ANS: A

a. 2-methyl-3-hexene

c. 2-bromo-3-methylbutane d. 2-methyl-2-butene ANS: B 22.

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

a. 1-methyl-4-nonyne b. 2-methyl-4-nonyne c. 2-methyl-3-nonyne d. 3-methyl-4-nonyne ANS: D ?

a. (E) 1,2-dibromobutene b. (Z) 1,2-dibromobutene

d. (Z) 2,3-dibromobutene ANS: C 24.

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

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a. (E) 3,4-dibromohexene b. (Z) 3,4-dibromohexene c. (E) 2,3-dibromohexene d. (Z) 2,3-dibromobutene ANS: A

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a. 2,3-dibromobutane

c. 2,3-dibromobutene d. 2,2-dibromobutane ANS: B 26.

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

a. 3,4-dibromohexane b. 3,3-dibromohexane c. (Z) 3,4-dibromohexene d. 3,3,4,4-tetrabromohexane ANS: D 27.

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

a. 2,3-dibromobutane b. 2,2,3,3-tetrabromobutane c. 2,3-dibromobutene d. 2,2-dibromobutane ANS: D

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a. 3,4-dibromohexane

c. (E) 3,4-dibromohexene d. 3,3,4,4-tetrabromohexane ANS: B

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b. cis-2-butene c. 2-butanol d. butanone ANS: A 30.

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

a. 2-hexanone b. hexanal c. 2-hexanol d. cis-2-hexene ANS: B

b. cis-2-butene c. 2-butanol d. butanone ANS: A 32.

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

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a. 2-hexanone b. hexanal c. 2-hexanol d. cis-2-hexene ANS: B

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b. 2 c. 3 d. 4 ANS: A 34.

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

a. 1 b. 2 c. 3 d. 4 ANS: D

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35.

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

a. 1 b. 2 c. 3 d. 4 ANS: D 36.

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

a. 1 b. 2 c. 3 d. 4 ANS: D

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37.

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

a. 1 b. 2 c. 3 d. 4 ANS: B

a. an alcohol

c. a 1,2-diene d. an epoxide ANS: B

a. 1 b. 2

d. 4 ANS: C

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40.

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

a. 1 b. 2 c. 3 d. 4 ANS: D

a. butane b. 1-butene c. cis-2-butene

ANS: D 42.

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

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a. 1 b. 2 c. 3 d. 4 ANS: B

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43.

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

a. butane b. 1-butene c. cis-2-butene d. trans-2-butene ANS: C

b. 2 c. 3 d. 4 ANS: A 45.

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

a. butane b. 1-butene c. cis-2-butene d. trans-2-butene ANS: C

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b. 2 c. 3 d. 4 ANS: A

a. 1 mole of Br2 b. 2 moles of Br2 c. 1 mole of HBr

ANS: D

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b. 2 moles of Br2 c. 1 mole of HBr d. 2 moles of HBr ANS: A

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49.

What is the best choice of reagent(s) to perform the following transformation?

a. H2O; H2SO4 b. 1. 3 moles of NaNH2; 2. H3O+ c. KMnO4, NaOH, H2O d. Zn ANS: B 50.

What is the best choice of reagent(s) to perform the following transformation?

a. H2/Pt b. H2/Lindlar catalyst c. Na/NH3 d. BH3; followed by H2O2, NaOH ANS: C

a. H2/Pt

c. Na/NH3 d. BH3; followed by H2O2, NaOH ANS: B 52.

What is the best choice of reagent(s) to perform the following transformation?

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a. H2/Lindlar catalyst b. Na/NH3 c. (sia)2BH; followed by H2O2, NaOH d. BH3; followed by H2O2, NaOH

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ANS: C 53.

What is the best choice of reagent(s) to perform the following transformation?

a. H2/Lindlar catalyst b. Na/NH3 c. (sia)2BH; followed by H2O2, NaOH d. BH3; followed by H2O2, NaOH ANS: D

b. 2 c. 3 d. 4 ANS: A 55.

What is the major organic product obtained from the following series of reactions?

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a. propanal, CH3CH2CHO b. 1-propanol, CH3CH2CH2OH c. butanal, CH3CH2CH2CHO d. butanone, CH3COCH2CH3

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ANS: D 56.

What is the major organic product obtained from the following series of reactions?

a. (E)-5-phenyl-2-pentene b. 6-phenyl-1-hexene c. (Z)-6-phenyl-2-hexene d. (E)-6-methyl-3-heptene ANS: C ?

a. (Z)-2-heptene b. (Z)-1,5-heptene c. 1-heptene

ANS: D 58.

What is the major organic product obtained from the following series of reactions?

a. (Z)-2-heptene b. (E)-2-heptene c. 1-heptene d. heptane ANS: B 59.

Which of the following reagents react with 2-butyne to form (Z)-2-butene

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1.

H2/Lindlar catalyst

2.

(sia)2BH followed by CH3COOH

3.

Na/NH3

a. only 1 b. only 2 c. only 3 d. only 1 and 2 ANS: D

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60.

Which of the following reagents react with 2-butyne to form butane

a. H2/Lindlar catalyst b. H2/Pd c. (sia)2BH followed by CH3COOH d. Na/NH3 ANS: B PROBLEM 1.

What is IUPAC name of the following compound?

ANS: (R)-4-chloro-2-pentyne 2.

What is IUPAC name of the following compound?

ANS: (S)-2-chloro-3-hexyne 3.

What is IUPAC name of the following compound?

ANS: 1,5-heptadiyne 4.

What is IUPAC name of the following compound?

ANS: 2,5-octadiyne

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5.

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

6.

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

7.

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

8.

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

ANS:

ANS:

ANS:

ANS:

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9.

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

10.

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

11.

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

12.

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

13.

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

ANS:

ANS:

ANS:

ANS:

ANS:

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14.

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

ANS:

ANS:

.

ANS:

17. Outline how one might achieve the following transformation, showing reagents and the isolated intermediates in the synthesitc scheme.

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ANS:

ANS:

.

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ANS:

20. Outline how one might achieve the following transformation, showing reagents and the isolated intermediates in the synthetic scheme.

ANS:

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