Chapter 16 - Test Bank Chem 200

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Package Title: Solomons Test Bank Course Title: Solomons 11e

Chapter Number: 16

Question type: Multiple Choice

1) What is the correct IUPAC name for the following compound?

O

a) 2-Methyl-5-heptanone b) 7-Methyl-4-octanone c) 6-Isopropyl-4-octanone d) Isobutyl propyl ketone e) 1,1-Dimethyl-4-heptanone Answer: B

Topic: Nomenclature Section: 16.2

Difficulty Level: Easy

2) What is the correct structure for 7-methyl-4-octanone?

O O O O I II III IV V O a) I b) II c) III d) IV e) V Answer: D Topic: Nomenclature 1

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Section: 16.2

O a) 5,5-Dimethyl-2-heptanone b) 5-Ethyl-5,5-dimethyl-Methyl-2-octanone c) 5-Ethyl-5-methyl- 2-hexanone d) 5,5-Dimethyl-2-octanone e) 3,3-Dimethyl-6-heptanone Answer: A Topic: Nomenclature Section: 16.2

4) What is the correct structure for 5,5-dimethyl-2-heptanone?

I II III IV V O H O O O O a) I b) II c) III d) IV e) V Answer: B Topic: Nomenclature Section: 16.2

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5) A correct name for the following compound would be which of those below? H O a) 2,5-Dimethyl-6-hexanal b) 2,5-Dimethylhexanal c) 2-Aldehydoisohexane d) 3,5-Dimethylheptanone e) 1-Hydro-2,5-dimethyl-1-hexanone Answer: B Topic: Nomenclature Section: 16.2

6) What is the correct structure for 2,5-dimethylhexanal?

I II _III IV V H O O O H O H O a) I b) II c) III d) IV e) V Answer: D Topic: Nomenclature Section: 16.2

7) What is the correct IUPAC name for the following compound? 3

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O a) 5,5-Dimethyl-2-heptanone b) 5-Ethyl-5,5-dimethyl-Methyl-2-octanone c) 5,5-Dimethylcycloheptanone d) 4,4-Dimethylcycloheptanone e) 3,3-Dimethylcycloheptanone Answer: D Topic: Nomenclature Section: 16.2

Difficulty Level: Medium

O a) 2,4-dimethyl-2-pentenone b) 2,5-dimethylcyclopenten-3-one c) 2,4-dimethylcyclopent-2-enone d) 3,5-dimethylcyclopent-2-enone e) 2-methyl-5-methylcyclopent-2-enone Answer: C Topic: Nomenclature Section: 16.2

O

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a) 1,1,2-Trimethyl-1,3-hexenone b) 1,2-Dimethyl-1,3-hexenone c) 2,3-Dimethyl-1,3-heptenone d) 2,3-Dimethyl-2-hepten-4-one e) 5,6-Dimethyl-5-hepten-4-one Answer: D Topic: Nomenclature Section: 16.2

10) What is the correct structure for 2,3-dimethyl-2-hepten-4-one?

O O O O O I _II III IV V a) I b) II c) III d) IV e) V Answer: E Topic: Nomenclature Section: 16.2

11) A correct name for C6H5CH2CH2CH O

is? a) 3-Benzylpropanone

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b) 3-Phenylpropanal c) 3-Benzylpropanal d) Nonanone e) Nonanal Answer: B Topic: Nomenclature Section: 16.2

12) What is the correct structure for 3-phenylpropanal?

O O O H H O O I II III IV V a) I b) II c) III d) IV e) V Answer: E Topic: Nomenclature Section: 16.2

13) What is the correct structure for 5-hydroxy-2-phenyl-3-hexanone?

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OH O OH Ph Ph OH O Ph Ph OH O Ph H O OH I II III IV V O a) I b) II c) III d) IV e) V Answer: C Topic: Nomenclature Section: 16.2

14) Which is the proper name for the structure shown?

CHO CH3 Cl a) 2-Chloro-5-aldehydotoluene b) 6-Chloro-3-aldehydotoluene c) 2-Methyl-4-aldehydochlorobenzene d) 4-Chloro-3-methylbenzaldehyde e) 4-Methyl-5-chloro-2-benzaldehyde Answer: D Topic: Nomenclature Section: 16.2

15) What is the correct structure for 4-chloro-3-methylbenzaldehyde?

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H O H O H O H O Cl Cl _Cl Cl H O Cl I II _III IV _V a) I b) II c) III d) IV e) V Answer: A Topic: Nomenclature Section: 16.2

16) What is the correct structure for 3-methyl-5-(2,5-dinitrophenyl)pentanal?

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O H O H O H O NO2 O2N O2N H O O2N O2N NO2 NO2 NO2 NO2 NO2 I II III _IV V a) I b) II c) III d) IV e) V Answer: B Topic: Nomenclature Section: 16.2

17) What is the correct structure for 3-methyl-5-(4-chlorophenyl)hexanal?

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H H H H Cl O Cl O O Cl Cl O Cl O I II III IV V a) I b) II c) III d) IV e) V Answer: D Topic: Nomenclature Section: 16.2

18) What is the correct structure for 7-bromo-1-octyn-4-one?

Br O O Br O Br Br O O Br I II III IV _V 10

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a) I b) II c) III d) IV e) V Answer: A Topic: Nomenclature Section: 16.2

O Br a)2-Methyl-2-bromobutanone b)(S)-2-Bromo-2-methylcyclobutanone c)(R)-2-Bromo-2-methylcyclobutanone d) (S)-1-Bromo-1-methyl-2-cyclobutanone e)(R)-1-Bromo-1-methyl-2-cyclobutanone Answer: B Topic: Nomenclature Section: 16.2

Difficulty Level: Hard

a)2-Bromobutanone b)(S)-2-Bromo-cyclobutanone c)(R)-2-Bromo-cyclobutanone d) (S)-1-Bromo-2-cyclobutanone e)(R)-1-Bromo-2-cyclobutanone Answer:C 11

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O Cl H a) (S)-3-chloro-1-hexanone b) (S)-1-chloro-3-hexanone c) (R)-3-chlorocyclohexanone d) (S)-3-chlorocyclohexanone e) (S)-1-chloro-3-cyclohexanone Answer: D Topic: Nomenclature Section: 16.2

a) (S)-3-chloro-1-hexanone b) (S)-1-chloro-3-hexanone c) (R)-3-chlorocyclohexanone d) (S)-3-chlorocyclohexanone e) (S)-1-chloro-3-cyclohexanone Answer:C Topic: Nomenclature Section: 16.2

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23) What is the correct IUPAC name for the following compound? a) (1S, 4R)-bicyclo[2.2.1]hexan-2-one b) (1S, 4R)-bicyclo[2.1.2]heptan-2-one c) (1S, 4R)-bicyclo[2.2.1]heptan-2-one d) (1R, 4S)-bicyclo[2.1.1]heptan-2-one e) (1S, 4S)-bicyclo[2.1.2]heptan-2-one Answer:C Topic: Nomenclature Section: 16.2

a) bicyclo[1.1.0]butan-2-one b) bicyclo[1.0.1]butan-2-one c) bicyclo[1.1.0]pentan-2-one d) bicyclo[0.1.1]butan-2-one e) bicyclo[1.0.1]pentan-2-one Answer:A Topic: Nomenclature Section: 16.2

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a) bicyclo[1.1.1]pentan-2-one b) bicyclo[1.1.0]pentan-2-one c) cyclopentanone d) methylenepentan-2-one e) bicyclo[1.0.1]pentan-2-one Answer:B Topic: Nomenclature Section: 16.2

26) What is the IUPAC name for

CH3 CH OH CH2 C CH O C6H5 CH3 ? a) 4-Oxo-5-phenyl-2-hexanol b) 5-Hydroxy-2-phenyl-3-hexanone c) 2-Hydroxy-5-phenyl-4-hexanone d) 2-Hydroxypropyl-1-phenylethyl ketone e) 5-Hydroxy-3-keto-2-phenylhexane Answer: B Topic: Nomenclature Section: 16.2

27) Which is the proper name for the structure shown? O₂N NO₂ O a) 3-Methyl-5-(1,4-dinitrobenzyl)-1-pentanal b) 3-Methyl-1-(2,5-dinitrophenyl)-5-pentanal c) 3-Methyl-5-(2,5-dinitrophenyl)pentanal d) 3-Methyl-5-(2,5-dinitrophenyl)pentanaldehyde e) 3-Methyl-5-(2,5-dinitrophenyl)pentaldehyde Answer: C Topic: Nomenclature 14

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Section: 16.2

28) Which is the proper name for the structure shown? O Cl a) 3,5-Dimethyl-5-(4-chlorobenzyl)-1-pentanal b) 3-Methyl-5-(4-chlorophenyl)hexanol c) 3,5-Dimethyl-5-(4-chlorophenyl)-1-pentanaldehyde d) 3-Methyl-5-(4-chlorophenyl)-hexanaldehyde e) 3-Methyl-5-(4-chlorophenyl)hexanal Answer: E Topic: Nomenclature Section: 16.2

29) Which is the proper name for the structure shown below? Br O a) 7-Bromo-1,4-octynal b) 7-Bromo-1,4-octynone c) 2-Bromo-5,7-octynal d) 7-Bromo-7-methyl-1-heptyne-3-ketone e) 7-Bromo-1-octyn-4-one Answer: E Topic: Nomenclature Section: 16.2

30) What is the correct structure for (R)-7-bromo-1-octyn-4-one?

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Br O O Br Br O O Br I II III IV _V Br O a) I b) II c) III d) IV e) V Answer: A Topic: Nomenclature Section: 16.2

31) What is the correct structure for (S)-7-bromo-1-octyn-4-one?

Br O O Br Br O O Br I II III IV _V Br O a) I b) II c) III d) IV e) V Answer: C 16

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32) Which is the IUPAC name for the structure shown below?

O Br H a) (R)-5-Bromo-2-heptanal b) (S)-5-Bromo-2-heptanal c) (R)-5-Bromo-2-heptanone d) (S)-5-Bromo-2-heptanone

e) (R)-3-Bromopentyl methyl ketone Answer: C

H Br O a) (R)-5-Bromo-2-heptanal b) (S)-5-Bromo-2-heptanal c) (R)-5-Bromo-2-heptanone d) (S)-5-Bromo-2-heptanone

e) (R)-3-Bromopentyl methyl ketone Answer: D

34) What is the correct structure for (R)-5-bromo-2-heptanone?

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Br H O H O Br H H O H Br O O H Br Br H I II III IV V a) I b) II c) III d) IV e) V Answer: B Topic: Nomenclature Section: 16.2

35) What is the correct structure for (S)-5-bromo-2-heptanone?

Br H O H O Br H H O H Br O O H Br Br H I II III IV V 18

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a) I b) II c) III d) IV e) V Answer: E Topic: Nomenclature Section: 16.2

O a) 5-Cyclohexyl-2-hexanal b) 5-Cyclohexyl-2-hexanone c) 5-Cyclohexyl-5-methyl-2-pentanone d) 5-(1-Methylcyclohexyl)-2-pentanone e) 4-(1-Methylcyclohexyl)-2-butanone Answer: E Topic: Nomenclature Section: 16.2

37) What is the correct structure for 4-(1-methylcyclohexyl)-2-butanone?

O O O O O I II III IV V a) I b) II c) III d) IV 19

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e) V Answer: D

38) What is the correct structure for (S)-4-cyclohexyl-3-methyl-2-butanone?

O O O O O I II III IV V a) I b) II c) III d) IV e) V Answer: C Topic: Nomenclature Section: 16.2

39) What is the correct structure for (S)-4-cyclohexyl-3-methyl-2-butanone?

a) I b) II

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c) III d) IV e) V Answer: E Topic: Nomenclature Section: 16.2

40) Which of the compounds listed below would you expect to have the highest boiling point? (They all have approximately the same molecular weight.)

a)Pentane b)1-Butanol c)Butanal d)1-Fluorobutane e)Diethylether Answer: B

Topic: Physical Properties, Relationships, Stereochemistry Section: 16.3

41) Stereoisomers can exist in the case of which of the following? a) The hydrazone of butanone

b) The oxime of acetone

c) The phenylhydrazone of cyclohexanone

d) The cyclic acetal formed from propanal and ethane-1,2-diol e) The imine of cyclopentanone

Answer: A

42) Stereoisomers can exist in the case of which of the following? a) The hydrazoneof benzophenone

b) The oxime of 2-methylcyclopentanone

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c) The phenylhydrazone of 4-methylcyclohexanone d) The imine of cyclopentanone

e) Two of these choices. Answer: B

43) In which of the following reactions is the final product expected to be formed as a racemic mixture? a) C6H5C O H C₆H₅MgBr + b) CH3CCH3 O HCN + c) H O + HCN d)CH3C O H + xs CH₃OH + HCl e) CH3CHCH2COC2H5 CH3 O + (i-Bu)₂AlH Answer: C

44)Acetals are unstable in the presence of an aqueous solution of which of these? a) HCl b) NaOH c) KHCO3 d) Na2CO3 e) NaCl 22

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Answer: A Topic: Reagents Section: 16.7

45) LiAlH4 (LAH) cannot be used to convert carboxylic acids to the corresponding aldehydes

because:

a) LAH is not sufficiently reactive. b) RCOOH is converted into RCOOLi. c) RCOOH is reduced to RCH2OH.

d) RCOOH is reduced to RCH3.

e) RCOOH is converted into R2C=O.

Answer: C Topic: Reagents Section: 16.4

46) Identify the reagent(s) that would bring about the following reaction: CH3CH2CH2COCl ⎯⎯⎯→ CH3CH2CH2CHO a) H2/Ni b) Li/liq.NH3 c) LiAlH[OC(CH3)3]3, ether d) NaBH4, CH3OH e) LiAlH4, ether Answer: C Topic: Reagents Section: 16.4

47) Which of these will not catalyze the reaction of a weak nucleophile with the carbonyl group of an aldehyde or ketone?

a) I -b) H3O+

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c) AlCl3 d) BF3 e) ZnCl2 Answer: A Topic: Reagents Section: 16.6

48) Which reagent(s) could be used to carry out the following transformation?

O

?

a) Zn(Hg), HCl, reflux b) LiAlH4, ether

c) HSCH2CH2SH, BF3; then Raney Ni (H2)

d) All of these choices. e) Two of these choices. Answer: E

Topic: Reagents Section: 16.7

49) The following reduction can be carried out with which reagent(s)?

O ?

a) Zn(Hg), HCl

b) i) HSCH2CH2SH, BF3 ; ii)Raney Ni (H2)

c) H2NNH2, KOH

d) None of these choices. e) All of these choices. Answer:E

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50) The following reduction can be carried out with which reagent(s)?

O ? a) Zn(Hg), HCl b) i) HSCH2CH2SH, BF3 ; ii)Raney Ni (H2) c) NaBH4, CH3OH d) Zn(Hg), HCl and i) HSCH2CH2SH, BF3 ; ii)Raney Ni (H2) e) Zn(Hg), HCl and NaBH4, CH3OH Answer: D Topic: Reagents Section: 16.7

51) Which reagent will not differentiate between 3-butenal and 2-butanone? a) Br2/CCl4

b) Ag2O,OH

-c) H2NNHC6H5

d) KMnO4,OH

-e) None of these choices. Answer: C

52) The compound C6H5C N N CC6H5 H H

is produced by the reaction of an excess of benzaldehyde with which compound?

a) Ammonia b) Hydrazine c) Nitrogen d) Phenylhydrazine e) Hydroxylamine 25

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Answer: B Topic: Reagents Section: 16.8

53) The migratory aptitude for groups attached to a ketone or aldehyde carbonyl during the Baeyer-Villiger oxidation is:

a) H >Ph- > 3° alkyl > 2° alkyl > 1° alkyl > methyl b) Ph- > H>3° alkyl>2° alkyl>1° alkyl>methyl c) 3° alkyl > 2° alkyl > 1° alkyl > methyl>H >Ph- d) 3° alkyl > 2° alkyl > 1° alkyl > methyl>Ph->H e) H > 3° alkyl > 2° alkyl > 1° alkyl > methyl>Ph- Answer:A

Topic: Mechanisms Section: 16.12

54) Dissolving benzaldehyde in methyl alcohol establishes an equilibrium with what compound?

a) C6H5CHOCH3 OH b) C6H5COCH3 O c) C6H5C(OCH3)3 d) C6H5CHOCH3 OH andC6H5COCH3 O e) C6H5COCH3 O andC6H5C(OCH3)3 Answer: A

Topic: Reaction Products Section: 16.7

55) Select the structure of the major product in the following reaction. 26

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? i) BH₃ ii) H₂O₂,OH-, H₂O a) Ethylbenzene b) 1-Phenylethanol c) Acetophenone d) 2-Phenylethanal e) Vinylbenzene Answer: D

56) Select the structure of the major product in the following reaction.

a) I b) II c) III d) IV e) V 27

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Answer:D

O CH₃COOOH a) I b) II c) III d) IV e) V Answer:C

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a) I b) II c) III d) IV e) V Answer:A

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a) I b) II c) III d) IV e) V Answer:B

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a) I b) II c) III d) IV e) V Answer:C

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?

i) BH

₃

ii) H

₂

O

₂

,OH

-

, H

₂

O

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OH O H I II III IV _V O OH a) I b) II c) III d) IV e) V Answer: D

64) What is the final product, Z, of the following synthesis?

CH3 COAl(t-Bu)2 O COCH3 O CH O COLi O COH O 1. KMnO₄, OH-_{, heat} 2. H₃O+ SOCl₂ 1. LiAlH(O-t-Bu)3 ether, -78 o_C 2. H₂O X Y Z I II III IV V a) I b) II c) III d) IV e) V 34

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Answer: C

65) Select the structure of the major product in the following reaction. ? H₂SO₄ HgSO₄, H₂O a) Ethylbenzene b) 1-Phenylethanol c) Acetophenone d) 2-Phenylethanal e) Vinylbenzene Answer: C

?

H

₂

SO

₄

HgSO

₄

, H

₂

O

OH O H I II III IV _V O a) I b) II 35

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c) III d) IV e) V Answer: C

i.) KMnO4, OH-, hot

ii) H3O+ ? OH OH OH O I II III IV V a) I b) II c) III d) IV e) V Answer: E

i.) KMnO4, OH-, hot

ii) H3O+

?

a) cyclopentanol

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b) 1-cyclopentylcyclopentane c) cyclopentanone

d) cyclopentene

e) 1-(1-hydroxycyclopentyl)-1-hydroxycyclopentane Answer: C

69) What would be the product of the following reaction sequence?

IV I II V III

?

1. DIBAL-H, -78oC. 2. H₂O O O O O H O OH H O O OH O OH a) I b) II c) III d) IV e) V Answer:C

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70) The product, K, of the following sequence of reactions I CH3CH2MgBr ether J Benzene CH3CHCOCl K CH3 AlCl₃ H₃O+ would be: OH HO O OH O I II III IV V a) I b) II c) III d) IV e) V Answer: B

Topic: Reaction Products Section: 16.5 and 16.6 Difficulty Level: Medium

71) The product, K, of the following sequence of reactions would be:

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Cl O AlCl3 I MgBr ether J H3O + heat (-H2O) K HO O OH I _II III IV V a) I b) II c) III d) IV e) V Answer: D

72)The product, J, of the following sequence of reactions would be:

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a) I b) II c) III d) IV

e) None of these choices. Answer:B

73) The product, E, of the following sequence of reactions

would be:

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O _OH Cl O I II III IV V a) I b) II c) III d) IV e) V Answer: C

would be:

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e) None of these choices. Answer:B

OH O PCl5 A B + C (discard) HS SH BF3 D Raney Ni H2 E AlCl3 would be: 42

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O Cl O I II III IV V a) I b) II c) III d) IV e) V Answer: C

76) The product, C, of the following reaction sequence,

CH₃CCH₃ O CN + HCN C₄H₇NO H2O H₂SO₄ heat C would be: a) CH2 CCOOH CH3 b) CH3CH2COOCH3 c) CH3CHCH3 CN d) CH3CH=CHCOOH

e) None of these choices. Answer: A

Topic: Reaction Products

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Section: 16.9

77) The product, D, of the following reaction sequence,

O -_CN HCN C4H7NO HCl H2O heat D would be: a) CH2 CCOOH CH3 b) CH3CH2COOCH3 c) CH3CHCH3 CN d) CH3CH=CHCOOH e) HO COOH Answer: E

78) What is the major product of the following reaction sequence?

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O HCN LiAlH4 H3O+ ? OH CN CN OH NH2 OH OH COOH I II III IV V a) I b) II c) III d) IV e) V Answer: C

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O HCN OH CN CN OH NH2 OH OH COOH I II III IV V HCl H2O heat OH a) I b) II c) III d) IV e) V Answer: E

O NOSO3H COH O CN OSO3H CN CNH2 H HCN H₂SO₄ H₂O heat I II III IV V a) I b) II c) III d) IV e) V 46

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Answer: B

81) The product, H, of the following reaction sequence,

F C6H5Li ether G C₆H₅CH₂Br + (C₆H₅)₃P C6H5CCH3 O H would be: a) C₆H₅CH₂CC₆H₅ CH₃ OH b) C6H5CH2CC6H5 O c) C6H5CH CHCC6H5 O d) C6H5CH2CH=CHC6H5 e) C6H5CH CCH3 C6H5 Answer: E

82) What would be the final product?

C₆H₅CCH₃ O CH₃I (C6H5)3P ether C₆H₅Li ? a) C6H5C CH2 CH3 47

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b) C6H5CCH3 C₆H₅ CH3 c) C6H5CH=CHCH3 d) C6H5CCH3 OH CH3 e) C6H5CH CC6H5 CH3 Answer: A

83) What would be the final product?

+ P(OEt)3 NaH O ? CH3I a) C6H5C CH2 CH3 b) C6H5CCH3 C6H5 CH3 c) C6H5CH=CHCH3 d) C6H5CCH3 OH CH3 e) C6H5CH CC6H5 CH3 Answer: A 48

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84) What is the reactant W in the synthesis given below?

O Ph₃P + W C₆H₅Li Wittig reagent a) Cyclopentanone b) Cyclopentene c) Cyclopentanol d) Bromocyclopentane e) Triphenylphosphine oxide Answer: D

85) Predict the major organic product of the following reaction:

O H HO₂C O O H3C O O H₃C O O H3C OH O H O H I II III IV V Ag(NH₃)₂+ H₂O ? a) I b) II 49

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c) III d) IV e) V Answer:B

86) The product, H, of the following reaction sequence,

Br + P(OEt)3 F NaH G O H would be: a) C₆H₅CH₂CC₆H₅ CH₃ OH b) C6H5CH2CC6H5 O c) C6H5CH CHCC6H5 O d) C6H5CH2CH=CHC6H5 e) C6H5CH CCH3 C6H5 Answer: E

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IV OH O I II V III OH O O OH i) SOCl₂ ii) C₆H₆, AlCl₃ iii) HSCH₂CH₂SH, BF₃ iv) Raney Ni (H₂) ? a) I b) II c) III d) IV e) V Answer: E

Topic: Reaction Products Section: 16.5 and 16.7 Difficulty Level: Hard

IV OH O I II V III O _OH i) PCl₃ ii) C₆H₆, AlCl₃ iii) HSCH₂CH₂SH, BF₃ iv) Raney Ni (H₂) ? OH 51

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a) I b) II c) III d) IV e) V Answer: B

IV OH O I II V III OH O O OH i) PCl₃ ii) C₆H₆, AlCl₃ iii) Zn(Hg), HCl, heat ? a) I b) II c) III d) IV e) V Answer: E

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IV OH O I II V III OH O O OH i) PCl₃ ii) C₆H₆, AlCl₃ iii) H2NNH2, KOH ? a) I b) II c) III d) IV e) V Answer: E

IV OH O I II V III OH O O OH i) PCl₅ ii) C₆H₆, AlCl₃ iii) Zn(Hg), HCl, heat ? 53

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a) I b) II c) III d) IV e) V Answer: E

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IV OH O I II V III OH O O OH i) SOCl₂ ii) C₆H₆, AlCl₃ iii) Zn(Hg), HCl, heat ? a) I b) II c) III d) IV e) V Answer: E

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IV OH O I II V III OH O OH i) PCl₃ ii) C₆H₆, AlCl₃ iii) NaBH₄, H₂O ? OH a) I b) II c) III d) IV e) V Answer: D

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IV OH O I II V III OH O OH i) PCl₃ ii) C₆H₆, AlCl₃ iii) LiAlH₄ iv) H₂O ? OH a) I b) II c) III d) IV e) V Answer: D

IV OH O I II V III OH O OH i) PCl₃ ii) C₆H₆, AlCl₃ iii) Zn(Hg), HCl, heat ? OH 57

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a) I b) II c) III d) IV e) V Answer: A

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99) The product, E, of the following reaction sequence, CH₃CH₂COOH PCl5 C6H6 AlCl3 NaBH₄ CH3OH C D E would be: CH₂CH₂CH₃ COCH₂CH₃ O CCH₂CH₃ O CHCH₂CH₃ OH CH(CH₃)₂ I II III IV V a) I b) II c) III d) IV e) V Answer: C

100) The product, D, of the following sequence of reactions

CH3CH2COH O SOCl₂ A toluene AlCl3 B Zn(Hg) HCl D + C (discard) would be: CH₃ CH₂CH₂CH₃ CH₃CH₂CCH₂ O CH₃ CH₂CH₂CCl O CH3 CH2CH2CH2Cl CH3 CH CH₃ CH₃ I II I IV V II a) I b) II c) III 59

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d) IV e) V Answer: A

101) The product, D, of the following sequence of reactions

would be: CH3 CH2CH2CH3 CH3CH2CCH2 O CH3 CH2CH2CCl O CH₃ CH₂CH₂CH₂Cl CH₃ CH CH₃ CH₃ I II I IV V II a) I b) II c) III d) IV e) V Answer: A

102)The product, D, of the following sequence of reactions

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would be: CH₃ CH₂CH₂CH₃ CH3CH2CCH2 O CH3 CH2CH2CCl O CH₃ CH₂CH₂CH₂Cl CH3 CH CH₃ CH3 I II I IV V II a) I b) II c) III d) IV e) V Answer: A

103) The product, E, of the following reaction sequence,

OH O PCl5 C C₆H₆ AlCl3 D LAH E would be: CH2CH2CH3 COCH2CH3 O CCH2CH3 O CHCH2CH3 OH CH(CH3)2 I II III IV V a) I b) II c) III d) IV 61

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e) V Answer: C

104) What is the final product of this synthetic sequence?

Benzene Br2 FeCl₃ Mg ether 1. C6H5CHO 2. H₃O+ H2Cr2O4 acetone ? a) C6H5CC6H5 O b) p-BrC6H4CH2C6H5 c) C6H5CH2COOH d) C6H5CH2CC6H5 O e) C6H5CH2C6H5 Answer: A

? i) H₂, Lindlar catalyst ii) O₃ iii)Zn, CH₃CO₂H a) 4-Methylhexanal b) 4-Methyl-1-hexanol c) 3-Methylhexanal d) 4,10-Dimethyldodecane-6,7-dione e) 4,10-Dimethyldodecane-6,7-diol Answer: A 62

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? i) H₂, P-2 ii) O₃ iii)Zn, CH₃CO₂H a) 4-Methylhexanal b) 4-Methyl-1-hexanol c) 3-Methylhexanal d) 4,10-Dimethyldodecane-6,7-dione e) 4,10-Dimethyldodecane-6,7-diol Answer: A

? i) H₂, Ni₂B ii) O₃ iii)Zn, CH₃CO₂H a) 4-Methylhexanal b) 4-Methyl-1-hexanol c) 3-Methylhexanal d) 4,10-Dimethyldodecane-6,7-dione e) 4,10-Dimethyldodecane-6,7-diol Answer: A

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? i) Li, NH₃(l) ii) O₃ iii)Zn, CH₃CO₂H a) 3-Methylhexanal b) 4-Methyl-1-hexanol c) 4-Methylhexanal d) 4,10-Dimethyldodecane-6,7-dione e) 4,10-Dimethyldodecane-6,7-diol Answer: C

109) What new compound will eventually be formed when HCl is added to a solution of pentanal in methanol? a) 1-Chloro-1-methoxypentane b) 1,1-Dimethoxypentane c) 1,1-Dihydroxypentane d) 1,1-Dichloropentane e) 1-Chloro-2-methoxypentane Answer: B

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O HCN H₂SO₄ H₂O heat LiAlH₄ H₃O+ ? OH CN CN OH NH2 OH OH COOH I II III IV V a) I b) II c) III d) IV e) V Answer: D

O HCN LiAlH4 H3O+ ? OH CN CN OH NH2 OH OH COOH I II III IV V HCl H2O heat OH 65

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a) I b) II c) III d) IV e) V Answer: D

? i) H₂, Lindlar catalyst ii) O₃ iii)Zn, CH₃CO₂H H O OH H O O O OH OH I II III IV V a) I b) II c) III d) IV e) V Answer: A

113) Which of the following reactions would yield benzaldehyde?

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a) C₆H₅CH₂Cl OH -H₂O heat b) C6H5CH(OCH3)2 H₃O+ c)

C₆H₅COOH 1. LiAlH4, ether

2. H₂O

d) Two of these choices. e) All of these choices. Answer: B

Topic: Synthesis Section: 16.7

114) Which of the following procedures would not yield 3-pentanone as a major product?

a) H₃O+ CH₃CH₂CN CH3CH2MgBr ether b) 1. O3 2. Zn/H+ c) H3O+ CH₃CH₂CN CH3CH2Li ether d) H O CH3CH2MgBr ether H3O+ PCC CH2Cl2 e) H3O+ CH3CH2CO2H CH₃CH₂MgBr ether Answer: E Topic: Synthesis Section: 16.4

115) A good synthesis of

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H O would be: H H2O, H2SO4 HgSO4 H 1. O3 2. Zn/H+ I II III OH _{1. KMnO} 4, NaOH, heat 2. H3O+ IV CN 1. DIBAL-H/-78oC 2. H2O a) I b) II c) III d) IV

e) All of these are equally useful. Answer: B

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H O would be: H H2O, H2SO4 HgSO4 H 1. O3 2. Zn/H+ I II III OH _{1. KMnO} 4, NaOH, heat 2. H3O+ IV COOCH3 1. DIBAL-H/-78 o_C 2. H2O a) I b) II c) III d) IV

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H O would be: H H2O, H2SO4 HgSO4 H 1. O3 2. Zn/H+ I II III OH _{1. KMnO} 4, NaOH, heat 2. H3O+ IV COCl 1. LiAl(OC(CH3)3)3H 2. H3O+ a) I b) II c) III d) IV

e) All of these are equally useful. Answer: C

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H O would be: H H₂O, H₂SO₄ HgSO4 H 1. O₃ 2. Zn/H+ I II III OH _{1. KMnO} 4, NaOH, heat 2. H₃O+ IV PCC CH2Cl2 OH a) I b) II c) III d) IV

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H O would be: H H2O, H2SO4 HgSO4 H 1. O3 2. Zn/H+ I II III OH _{1. KMnO} 4, NaOH, heat 2. H3O+ IV 1. DMSO, (COCl)₂ 2. Et₃N OH a) I b) II c) III d) IV

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H O would be: H 1. BH3 2.H2O2, NaOH CN 1. DIBAL-H/-78oC 2. H2O COOCH3 1. DIBAL-H/-78 o_C 2. H2O COCl 1. LiAl(OC(CH3)3)3H 2. H3O+ I II III IV a) I b) II c) III d) IV

e) All of these are equally useful. Answer: E

121) Which synthesis or syntheses would yield propanal?

a)

CH₃CH₂CH₂OH PCC

CH₂Cl₂

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b) CH3CH2CCl O LiAlH[OC(CH₃)₃]₃ ether, -78 o_C c) CH₃C CH 1. Sia₂BH 2. H2O2, OH

-d) All of these choices. e) None of these choices. Answer: D

a) b) CH3CH2CCl O LiAlH[OC(CH₃)₃]₃ ether, -78 o_C c) CH₃C CH 1. Sia₂BH 2. H₂O₂, OH -d) All of these choices. e) None of these choices. Answer: D

a)

CH₂Cl₂

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b) CH3CH2CCl O LiAlH[OC(CH₃)₃]₃ ether, -78 o_C c)

d) All of these choices. e) None of these choices. Answer: D

a)

CH₂Cl₂

b)

c)

75 a)

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b)

c)

126) Which of the reactions listed below would serve as a synthesis of acetophenone,

C₆H₅CCH₃ O ? a) OH PCC CH2Cl2 b) C6H6 + CH3COCl AlCl₃ c) C6H5CN + CH3Li ether H₃O+

d) Two of these choices. e) All of these choices. Answer: E

127) Which of the reactions listed below would serve as a synthesis of acetophenone,

C₆H₅CCH₃ O

?

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a)

b) C6H6 + CH3COCl

AlCl₃

c) C6H5CN + CH3Li

ether H₃O+

128) Which of the following would yield 3-pentanone as the major product?

a) CH3CH2CN + CH3CH2Li ether H3O+ Product b) CN + _MgBr ether Product H3O + c) OH PCC CH₂Cl₂

129) Which sequence of reactions would be utilized to convert

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O CO2CH3 O C CH3 CH3 OH into ? a) 2CH3MgBr, then NH4+

b) HOCH2CH2OH, H3O+; LiAlH4, ether; 2CH3MgBr, then NH4+

c) HOCH2CH2OH, H3O+; 2CH3MgBr, then NH4+

d) HOCH2CH2OH, H3O+; H2, Pt; CH3OH, NH4+

e) None of these choices. Answer: C

130) Which of the following procedures would not yield (CH3)2CHCH O as a product? PCC OH CO2H OH O O CH2Cl2 SOCl₂ ether, -78 o_C O₃ Zn HOAc KMnO₄ NaOH H₃O+ H₃O+ I II III IV V LiAlH(O-t-Bu)₃ a) I b) II c) III d) IV e) V Answer: D Topic: Synthesis Section: 16.4 and 16.7 78

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131) Which of the following procedures would not yield (CH3)2CHCH O as a product? a) I b) II c) III d) IV e) V Answer: D Topic: Synthesis Section: 16.4 and 16.7 Difficulty Level: Medium

132) Which reaction sequence would be used to prepare

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O H O Cl O MgBr + 1. ether 2. H3O+ H₂ Ni I + 2 CH₃MgBr 1. ether 2. H₃O+ H₂ Ni II III (C6H5)3P C6H5Li cyclopentanone H2 Ni IV CH3MgBr ether H₃O+ ? a) I b) II c) III d) IV

e) All of these choices would yield the product. Answer: C

133) Which Wittig reagent would be used to synthesize

CH=P(C6H5)3 P(C6H5)3 CH₃CH=P(C₆H₅)₃ CH₃CH₂CH=P(C₆H₅)₃ I II III IV ? a) I b) II c) III d) IV

e) Either I or II could be used.

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Answer: E Topic: Synthesis Section: 16.10

134) Which of the following is not a synthesis of benzophenone,

C₆H₅CC₆H₅ O ? a) C6H5CCl O C₆H₆ + AlCl3 b) (C₆H₅)₂CHOH H2CrO4 acetone c) (C6H5)2CH=CH2 1. O₃ 2. Zn, HOAc d) Ph2CHOH PCC CH₂Cl₂

e) All of these choices will give benzophenone. Answer: E

C6H5CC6H5 O ? a) C₆H₅CCl O C₆H₆ + AlCl3 b) (C₆H₅)₂CHOH H2CrO4 acetone 81

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c)

(C₆H₅)₂CH=CH₂ 1. O3

2. Zn, HOAc

d)

C6H5CC6H5 O ? a) C₆H₅CCl O C₆H₆ + AlCl3 b) Ph₂CHOH PCC CH₂Cl₂ c) (C6H5)2CH=CH2 1. O₃ 2. Zn, HOAc d)

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H O H OH H H H2O, H2SO4 HgSO₄ I II 1. Sia2BH 2. H₂O₂, NaOH III 1. O3 2. Zn, HOAc

1. KMnO₄, NaOH, heat

2. H₃O+ IV would be: a) I b) II c) III d) IV

138) Which of the following is a synthesis of 3-heptanone?

a) b) CH₃CH₂CN CH3(CH2)2CH2Li H3O + ether c) CH₃CH₂CH₂CH₂OH PBr3 NaCN CH3CH2MgBr ether H₃O+ ether d) 83

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1. O₃

2. Zn/H+

e) All of these choices are syntheses of 3-heptanone. Answer: E

139) Which of the following is a synthesis of 3-heptanone?

a) b) CH₃CH₂CN CH3(CH2)2CH2Li H3O + ether c) CH₃CH₂CH₂CH₂OH PBr3 NaCN CH3CH2MgBr ether H₃O+ ether d) 1. O₃ 2. Zn/H+

e) All of these choices are syntheses of 3-heptanone. Answer: E

140) What, in general, is the order of decreasing reactivity of these carbonyl compounds towards nucleophilic reagents? CH3CCH3 CH3C O (CH3)3CCCH3 HC O (CH3)3CCC(CH3)3 O H O H O I II III IV V a) I > III > IV> II > V b) IV > II > I > III > V c) V > III > I > II > IV 84

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d) I>IV>II>III>V e) III > V > IV > II > I Answer: B

Topic: Carbonyl Reactivity Section: 16.6

141) Which of these gem-diols is expected to be the most stable?

a) CF3CCF3 OH OH b) CH3CH(OH)2 c) CH3CCH3 OH OH d) C6H5CH(OH)2 e) ClCH2CH(OH)2 Answer: A

142) Which of these gem-diols is expected to be the least stable?

a) CF3CCF3 OH OH b) CH3CH(OH)2 c) CH3CCH3 OH OH d) C6H5CH(OH)2 e) ClCH2CH(OH)2 85

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Answer: C

143) What, in general, is the order of increasing reactivity of these carbonyl compounds towards nucleophilic reagents? CH3CCH3 CH3C O (CH3)3CCCH3 HC O (CH3)3CCC(CH3)3 O H O H O I II III IV V a) I < III < V < II < IV b) IV < II < I < III < V c) V< III < I < II < IV d) II< I < V < III < IV e) III < V < IV < II < I Answer: C

144) Which of the following compounds is an acetal?

I OCH₃ O O II O OH O III O O IV O O a) I b) II c) III d) IV

e) None of these choices. Answer: C

Topic: New Functional Groups Section: 16.7

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145) Which is the general formula for a thioacetal? a) RC S H b) RCHSR' OH c) RCHSR' SH d) RCHSR' SR' e) RCHOR' SR' Answer: D

146) Which compound is an acetal?

I O OH III O O IV O OH II O OCH₃ a) I b) II c) III d) IV

e) All of these choices. Answer: B

147) Which compound is a hemiacetal?

I O OH III O O IV O OH II O OCH₃ 87

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e) All of these choices. Answer: A

148) Which of the following is formed when 3-methylcyclopentanone reacts with hydroxylamine? N-NH-C₆H₅ N-NH₂ N-OH I II III N N H NH₂ O IV N N H _NO 2 NO₂ V a) I b) II c) III d) IV e) V Answer: C

Topic: Reactions of Aldehydes and Ketones Section: 16.8

149) Which of the following is formed when 4-methylpentanal reacts with phenylhydrazine?

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N-NH-C6H5 N-C6H5 N-NH2 I II III IV V N N H NH2 O N=N-C6H5 a) I b) II c) III d) IV e) V Answer: A

150) Which of the following is formed when 2,2,3-trimethylcyclohexanone reacts with hydroxylamine? N-NH-C₆H₅ N-NH₂ II N-OH III I N N H NH2 O IV N N H _NO 2 NO₂ V a) I b) II c) III d) IV e) V Answer: C

Topic: Reactions of Aldehydes and Ketones 89

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Section: 16.8

151) Which of the following is formed when 2,2,3-trimethylcyclohexanone reacts with hydrazine? N-NH-C₆H₅ N-NH₂ II N-OH III I N N H NH₂ O IV N N H _NO 2 NO₂ V a) I b) II c) III d) IV e) V Answer: B

152) A compound with formula C5H10O gives two signals only, both singlets, in the 1H NMR

spectrum. Which of these structures is a possible one for this compound?

a)CH3CH2CCH2CH3 O b)(CH3)2CHCCH3 O c)(CH3)3CC O H d) CH₃CH₂CHC O H CH₃ 90

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e)(CH3)2CHCH2C O H

Answer: C

Topic: Spectroscopy Section: 16.14

153) A compound with formula C5H10O gives two signals only, one a triplet and the other a

quartet, in the 1H NMR spectrum. Which of these structures is a possible one for this compound?

a) CH3CH2CCH2CH3 O b) (CH3)2CHCCH3 O c) (CH3)3CC O H d) CH₃CH₂CHC O H CH₃ e) (CH3)2CHCH2C O H Answer: A Topic: Spectroscopy Section: 16.14

154) The1H NMR spectrum of a compound with formula C7H14O gives three signals. Which of

these structures is a possible one for this compound? a) 2-Heptanone

b) 3-Heptanone

c) 2,4-Dimethyl-3-pentanone d) 2,2-Dimethyl-3-pentanone e) Two of these choices. Answer: D

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155) The1H NMR spectrum of a compound with formula C7H14O gives two signals. Which of

b) 3-Heptanone

c) 2,4-Dimethyl-3-pentanone d)2,2-Dimethyl-3-pentanone e) Two of these choices. Answer: C

156) The13C NMR spectrum of a compound with formula C7H14O gives three signals. Which of

b) 3-Heptanone

c) 2,2-Dimethyl-3-pentanone d) 2,4-Dimethyl-3-pentanone e) Two of these choices. Answer: D

157) The13C NMR spectrum of a compound with formula C7H14O gives five signals. Which of

b) 3-Heptanone

c) 2,2-Dimethyl-3-pentanone d) 2,4-Dimethyl-3-pentanone e) Two of these choices.

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Answer: C

158) The1H NMR spectrum of a compound with formula C7H14O gives a doublet at 9.2 ppm.

Which of these structures is a possible one for this compound? a) 2-Methyl-3-hexanone

b) 2-Methylhexanal c) 2,2 -Dimethylpentanal d) 2,2-Dimethyl-3-pentanone e) Two of these choices. Answer: B

Question type: Molecular Drawing

159) Suggest a synthetic strategy for the synthesis of 4-methylpentanal from 3-methyl-1-bromobutane.

Answer: Br CN

NaCN i. DIBAL-H

ii. H₂O

O

Topic: Synthetic Strategy Section: 16.4

160) Suggest a synthetic strategy for the synthesis of 3-heptanone from 1-bromobutane.

Answer:

BrNaCN CN

O

i. C2H5Li, Et2O ii. H₃O+

Topic: Synthetic Strategy

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Section: 16.5

161) Suggest a synthetic strategy for the synthesis of 4-methylpentanal from 3-methyl-1-bromobutane.

Answer:

Br NaCN CN i. DIBAL-H_{ii. H}

2O

O

HBr ROOR

162) Suggest a synthetic strategy for the synthesis of 6-methyl-3-heptanol from 4-methylpentanenitrile, (CH3)2CHCH2CH2CN. Answer: CN CN OR OH OH i. DIBAL-H ii. H₂O iii. C₂H₅MgBr, Et₂O iv. H₃O+ i. C₂H₅MgBr, Et₂O ii. H₃O+ iii. NaBH₄, H₂O Topic: Synthetic Strategy

Section: 16.5

163) Suggest a synthetic strategy for the synthesis of 3-heptanone from 1-butene. Answer: Br NaCN CN O i. C₂H₅Li, Et₂O ii. H₃O+ HBr ROOR

Topic: Synthetic Strategy

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Section: 16.5

164) Cis-stilbene (cis-1,2-diphenylethene) can be prepared in high yield from its trans diastereomer. Propose a reasonable synthesis.

H H Ph Ph Ph H Ph H multiple steps trans-stilbene cis-stilbene Answer: H H Ph Ph m-CPBA O H Ph Ph H _Ph 3P Ph Ph H H O PPh3 Ph H Ph H

165) Complete the following reaction sequence, giving structural details of all significant intermediates and the final product.

H OH O H+ Answer: H OH O H+ O OH

Topic: Reaction Sequence Section: 16.7

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166) In the total synthesis of the Cecropia juvenile hormone, the following sequence of reactions were used. Draw the intermediate and final product formed.

O H HO O / H+ 1. CH3Li 2. H+_/H 2O ? Answer: O H HO O / H+ O H O O 1. CH3Li 2. H+_/H 2O HO H HO CH3

167) Complete the following reaction sequence, giving structural details of all significant intermediates. 1. OsO4 2. NaHSO3 H O H+ ? Answer: 1. OsO4 2. NaHSO3 H O H+ OH OH O O

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168) Complete the following reaction sequence, giving structural details of all significantintermediates and the final product.

O + _HO _H O H+ _KMnO₄_{, OH}-_{, heat} _H+ H2O ? Answer: O + _HO _H O H+ _KMnO 4, OH-, heat H+ H₂O O H O O O O O O HO OH O

169) Complete the following reaction sequence, giving structural details of all significant intermediates X, Y, and final product Z.

CH3 1. KMnO₄, OH-_{, heat} 2. H₃O+ SOCl₂ 1. LiAlH(O-t-Bu)3 ether, -78 o_C 2. H₂O X Y Z Answer: COOH COCl X Y _Z CHO

170) Complete the following reaction sequence, giving structural details of all significant intermediates.

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? i. Br₂, hν ii. Mg, CH₃CH₂CN iii. H₃O+ iv. NaBH₄ Answer: Br O NaBH₄ Br₂, hν i. Mg, CH₃CH₂CN ii. H₃O+ HO

171) Complete the following reaction sequence, giving structural details of all significant intermediates. O i. EtMgBr ii. H3O+, heat i. O3 ii.Zn, CH3CO2H ? Answer: O HO O O i. EtMgBr ii. H₃O+, heat i. O₃ ii.Zn, CH₃CO₂H

Benzene Br2 FeCl₃ Mg ether 1. C₆H₅CHO 2. H₃O+ H₂Cr₂O₄ acetone ? Answer: Br _MgBr OH O

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Answer:

Topic: Reaction Sequence Section: 16.5 and 16.12 Difficulty Level: Hard

Question type: Essay

174) Aldehydes are more reactive than ketones towards nucleophilic substitution because of both steric and electronic factors. Briefly explain.

a) Steric reasons: ___. b) Electronic reasons: ___.

Answer: a) aldehydes have a small hydrogen substituent on one side, so less steric crowding than ketones with alkyl groups either side of the carbonyl carbon.

b) aldehydes have only one electron-releasing group to partly neutralize/stabilize the partial positive charge at the carbonyl carbon while ketones have two

Topic: Relative Reactivity Section: 16.6

Question type: fill-in-the-blank

175) A compound with an OH and OR group attached to the same carbon is known as a(n) ___. Answer: hemiacetal

Topic: Hemiacetals Section: 16.7

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176) A compound with two OH groups attached to the same carbon is known as a(n) ___. Answer: hydrate or gem-diol

Topic: Hydrates Section: 16.7

177) A compound with two OR groups attached to the same carbon is known as a(n) ___. Answer: acetal

Topic: Acetals Section: 16.7

178) A compound with an OH and CN group attached to the same carbon is known as a(n) ___. Answer: cyanohydrin

Topic: Cyanohydrins Section: 16.9

179) A compound containing a C=N double bond is known as a(n) ___. Answer: imine

Topic: Imines Section: 16.8

180) 2,4-DNP is a reagent frequently used for functional group tests; it detects the presence of ___.

Answer: aldehydes and ketones Topic: Functional Group Tests Section: 16.8

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181) Oximes are formed when aldehydes and ketones react with ___. Answer:hydroxylamine, NH2OH

Topic: Functional Group Tests Section: 16.8

182) The reaction between a phosphorus ylide and an aldehyde or ketone is called the ___ reaction.

Answer: Wittig

Topic: Wittig Reaction Section: 16.10

183) The driving force for the Wittig reaction is the formation of the very strong ___ bond in ___.

Answer: P-O bond; triphenylphosphine oxide Topic: Wittig Reaction

Section: 16.10

184) The conversion of a trans epoxide to a cis alkene using triphenylphosphine is an example of a ___ reaction.

Answer: stereospecific Topic: General

Section: 16.10

185) The conversion of a cis epoxide to a trans alkene using triphenylphosphine is an example of a ___ reaction.

Answer: stereospecific Topic: General

Section: 16.10

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Question type: Molecular Drawing

186) Draw a complete mechanism, using arrow convention to indicate electron movement, for the following transformation:

Answer: O H N H+ O H N H N H HO ~H+ N H₂O -H2O N H -H+ N 102

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Topic: Mechanisms Section: 16.8

187) Draw a complete mechanism, using arrow convention to indicate electron movement,for the following transformation: O H3C H H CH3 + PPh3 H3C CH3 H H + Ph₃P O Answer: O H3C H H CH3 + PPh3 H3C H H H3C O PPh3 rotation 180o as shown H3C CH3 H H O PPh3 H3C CH3 H H O PPh3 H3C CH3 H H + _Ph₃_P O Topic: Mechanisms Section: 16.10

188) Draw a complete mechanism, using arrow convention to indicate electron movement, for the following transformation:

O H H H3C CH3 + PPh₃ H CH3 H C3 H + _Ph₃_P O Answer: 103

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O H H H3C CH3 + PPh3 H H H3C H3C O PPh3 rotation 180o as shown H CH3 H CH3 O PPh3 H CH3 H CH3 O PPh3 H CH3 H3C H + _Ph₃_P O Topic: Mechanisms Section: 16.10

Question type: fill-in-the-blank

189) The Tollens test, used in conjunction with 2,4-DNP, can distinguish between ___ and ___. Answer: aldehydes and ketones

Topic: Functional Group Tests Section: 16.13

Question type: Essay

190) What reagent would help you distinguish between acetophenone and 2-methylbenzaldehyde?

Answer: Tollen’s Reagent Topic: Functional Group Tests Section: 16.13

191) Explain clearly how you might use 1H NMR to distinguish between 2-phenylacetaldehyde and acetophenone.

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Answer: A quick inspection of 1H NMR of the two substances would allow easy identification and distinction between them: the expected 1H NMR spectra of the two substances are described below.

2-Phenylacetaldehyde Acetophenone C6H5CH2CHO and C6H5COCH3

3 signals 2 signals approximateδ ppm approximate δ ppm doublet (-CH2-) 2.5 singlet (-CH3) 2.0 multiplet (C6H5) 7 multiplet (C6H5) 7.2 triplet(-CHO) 9 Topic: Spectroscopy Section: 16.14

192) Propose a structure that fits the following spectroscopic data: C5H10O

IR: 1720 cm−1

1_{H NMR: 1.9δ (triplet, 3H), 1.7δ (sextet, 2H), 2.1δ (singlet, 3H), 2.4δ (triplet, 2H)}

Answer: CH3CH2CH2CCH3

O

193) Propose a structure that fits the following spectroscopic data: C5H10O IR: 1720 cm−1 1_{H NMR: 1.1δ (triplet, 3H), 2.4δ (quartet, 2H)} Answer: O Topic: Spectroscopy Section: 16.14 105

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IR: 1680 cm−1

1_{H NMR: 1.25δ (triplet, 3H), 3.0δ (quartet, 2H), 7-8δ (complexmultiplet, 5H)}

Answer:

O

195) Propose a structure that fits the following spectroscopic data: C7H6O IR: 1703 cm−1 1_{H NMR: 7-8δ (complexmultiplet, 5H), 10.0δ (singlet, 1H)} Answer: H O Topic: Spectroscopy Section: 16.14

IR: 1730 cm−1

(107)

1_{H NMR: 1.1δ (triplet, 3H), 2.5δ (doubletofquartets, 2H), 9.8δ (doublet, 1H)} Answer: H O Topic: Spectroscopy Section: 16.14

IR: 1716 cm−1

Broadband decoupled 13C NMR: 7.93, 35.50, 212.07δ

DEPT Experiments show: signal at 7.93 δ as CH3 and signal at 35.50 δ as CH2

Answer: O

IR: 1717 cm−1

Broadband decoupled 13C NMR: 13.70, 17.41, 29.78, 45.71, 208.93δ

DEPT Experiments show: signals at 13.70, 29.78 δ as CH3 and signals at 17.41, 45.71 δ

as CH2

Answer:CH3CH2CH2CCH3

O

(108)

IR: 1728 cm−1

Broadband decoupled 13C NMR: 13.71, 15.69, 45.82, 202.80δ

DEPT Experiments show: signal at 13.71 δ as CH3 and signals at 15.69, 45.82 δ as CH2

Answer: H

O

IR: 1708 cm−1

Broadband decoupled 13C NMR: 24.61, 26.42, 44.31, 213.81δ DEPT Experiments show: signals at 24.61, 26.42 δ as CH3

Answer: O

(109)

IR: 1737 cm−1

Broadband decoupled 13C NMR: 15.48, 41.07, 204.86δ

DEPT Experiments show: signal at 41.07 δ as CH and signal at 15.48 δ as CH3

Answer:

H

O

IR: 1728 cm−1

Broadband decoupled 13_{C NMR: 22.59, 23.57, 52.66, 202.71 δ}

DEPT Experiments show: signal at 23.57 δ as CH, signal at 22.59 δ as CH3, and signal at

52.66 δ as CH2.

Answer: H

O

203) Acetaldehyde is reacted with excess methanol in acid. The product was isolated and gave the following 1H NMR spectroscopic data:

1.3 δ (doublet, 3H) 3.4 δ (singlet, 6H)

(110)

4.6 δ (quartet, 1H)

Propose a structure consistent with this information. Answer:

O O