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Organic Chemistry 7th Edition Wade Test Bank

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Organic Chemistry 7th Edition Wade Test Bank

ISBN-13: 978-0321592316

ISBN-10: 032159231X

 

 

Description

Organic Chemistry 7th Edition Wade Test Bank

ISBN-13: 978-0321592316

ISBN-10: 032159231X

 

 

 

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Organic Chemistry, 7e (Wade)

Chapter 19   Amines

 

1) Which of the following is not an alkaloid?

  1. A) cocaine
  2. B) mesitylene
  3. C) nicotine
  4. D) mescaline
  5. E) morphine

Answer:  B

Diff: 1

Section:  19.1

 

2) Sec-Butylamine is the common name of what compound?

  1. A) 1-butanamine
  2. B) 2-butanamine
  3. C) N-methyl-1-propanamine
  4. D) N-methyl-2-propanamine
  5. E) N-ethylethanamine

Answer:  B

Diff: 2

Section:  19.2

 

3) Identify the correct  systematic name for the following compound.

 

 

  1. A) N,N-diethyl-5-hydroxycyclohex-1-enamine
  2. B) N,N-diethyl-4-hydroxycyclohex-1-en-2-amine
  3. C) 3-(diethylamino)cyclohex-3-enol
  4. D) 2-(diethylamino)cyclohex-1-en-4-ol

Answer:  C

Diff: 2

Section:  19.2

 

 

4) Provide the correct IUPAC name for the following amine.

 

  1. A) 4-(methylamino)-2-methyl-1-pentene
  2. B) 2,N-dimethyl-1-penten-4-amine
  3. C) 4,N-dimethyl-4-penten-2-amine
  4. D) 1,3,N-trimethyl-3-buten-1-amine

Answer:  C

Diff: 3

Section:  19.2

5) Provide the structure of N-ethyl-1-butanamine.

Answer:  CH3CH2CH2CH2NHCH2CH3

Diff: 1

Section:  19.2

 

6) Draw the structure of N-ethyl-N-methyl-1-hexanamine.

Answer:

Diff: 2

Section:  19.2

 

7) Provide the structure of 2,4-dimethylpyridine

Answer:

Diff: 2

Section:  19.2

 

8) Provide the IUPAC name for the compound shown below.

 

Answer:  3,3-dimethyl-1-butanamine

Diff: 2

Section:  19.2

 

 

9) Provide the IUPAC name of (CH3)3CCH2CH2NHCH2CH3.

Answer:  N-ethyl-3,3-dimethyl-1-butanamine

Diff: 2

Section:  19.2

 

10) Provide the name of (CH3CH2)4N+ Cl-.

Answer:  tetraethylammonium chloride

Diff: 2

Section:  19.2

11) Provide the name of the compound shown below.

 

Answer:  6-amino-1-methylcyclohexene

Diff: 2

Section:  19.2

 

12) Draw the structure of 3-pentanamine.

Answer:

Diff: 1

Section:  19.2

 

13) Provide the systematic name for the compound below.

 

(CH3)4N+Cl-

Answer:  tetramethylammonium chloride

Diff: 1

Section:  19.2

 

14) Draw the structure of 2,3-dimethyl-2-butanamine

Answer:

Diff: 2

Section:  19.2

 

 

15) Draw the structure of piperidine.

Answer:

Diff: 2

Section:  19.2

16) Draw the structure of N-propyl-4-methyl-3-octanamine.

Answer:

Diff: 2

Section:  19.2

 

17) Provide the name for the compound below.

 

Answer:  pyrrole

Diff: 2

Section:  19.2

 

18) Provide the systematic name for the compound below.

 

Answer:  4-aminocyclohexanone

Diff: 2

Section:  19.2

 

19) Provide the systematic name for the compound below.

 

Answer:  2-bromo-N-methylaniline

Diff: 2

Section:  19.2

 

 

20) Which of the following is a tertiary amine?

  1. A) cyclohexylamine
  2. B) 3-pentanamine
  3. C) methylamine
  4. D) N,N-dimethylaniline
  5. E) N-ethyl-1-propanamine

Answer:  D

Diff: 1

Section:  19.3

21) Which of the following is a secondary amine?

  1. A) cyclohexylamine
  2. B) 3-pentanamine
  3. C) methylamine
  4. D) N,N-dimethylaniline
  5. E) N-ethyl-1-propanamine

Answer:  E

Diff: 1

Section:  19.3

 

22) Which of the following amines is most soluble in water?

  1. A) pyrrolidine
  2. B) PhNH2
  3. C) (CH3)3N
  4. D) (CH3CH2CH2)2NH
  5. E) ethylamine

Answer:  E

Diff: 1

Section:  19.3

 

23) Which of the following compounds is a 2° amine?

  1. A) cyclohexylamine
  2. B) t-butylamine
  3. C) N-ethylaniline
  4. D) N,N-diethylaniline
  5. E) N-butylpyridinium bromide

Answer:  C

Diff: 1

Section:  19.3

 

 

24) Which of the following amines can be resolved into enantiomers?

  1. A) trimethylamine
  2. B) 3-pentanamine
  3. C) 2-pentanamine
  4. D) dimethylammonium chloride
  5. E) 4-(dimethylamino) pyridine

Answer:  C

Diff: 2

Section:  19.3

 

25) The nitrogen atom of trimethylamine is __________ hybridized which is reflected in the CNC bond angle of __________.

  1. A) sp, 180°
  2. B) sp2, 120°
  3. C) sp2, 108°
  4. D) sp3, 120°
  5. E) sp3, 108°

Answer:  E

Diff: 2

Section:  19.3

26) The nitrogen’s lone pair in pyrrolidine is best described as occupying what type of orbital?

  1. A) s
  2. B) sp3
  3. C) sp2
  4. D) sp
  5. E) p

Answer:  B

Diff: 2

Section:  19.3

 

27) Which of the following compounds containing a tertiary amine?

 

1)   2-methyl-2-propanamine

2)   N-ethylpyrrolidine

3)   N-methylcyclohexylamine

4)   2-(dimethylamino)butanal

  1. A) 1
  2. B) 4
  3. C) 3
  4. D) 2 and 4
  5. E) 1 and 3

Answer:  D

Diff: 2

Section:  19.3

 

 

28) Circle all of the following structures that can be resolved into pure enantiomers.

 

Answer:

Diff: 3

Section:  19.3

 

29) Why can’t N-methyl-2-propanamine be resolved into isolable enantiomers even though the compound is chiral?

Answer:  Enantiomers interconvert rapidly via nitrogen inversion.

Diff: 2

Section:  19.3

 

30) Why can 1,2,2-trimethylaziridine be resolved into enantiomers while

N-methyl-1-propranamine cannot?

Answer:  In 1,2,2-trimethylaziridine the nitrogen atom is contained in a 3-membered ring and cannot readily achieve the sp2 transition state required for nitrogen inversion. Introduction of an sp2 center in a 3-membered ring greatly increases the angle strain.

Diff: 3

Section:  19.3

31) Arrange the following compounds in order of increasing boiling point:

 

CH3NHCH2CH3, CH3OCH2CH3, (CH3)3N, and CH3CH2CH2OH.

Answer:  (CH3)3N  <  CH3OCH2CH3  <  CH3NHCH2CH3  <  CH3CH2CH2OH

Diff: 2

Section:  19.4

 

32) Arrange the following compounds in order of increasing boiling point:

ethyl methyl ether, 1-propanol, N-methylethanamine, and 1-propanamine.

Answer:  ethyl methyl ether < N-methylethanamine < 1-propanamine <  1-propanol

Diff: 2

Section:  19.4

 

33) Arrange the following in order of increasing basicity:

aniline, p-nitroaniline, p-toluidine, and p-methoxyaniline.

Answer:  p-nitroaniline < aniline < p-toluidine < p-methoxyaniline

Diff: 2

Section:  19.4

 

 

34) Which has the higher boiling point, butan-1-ol or 1-butanamine? Explain briefly.

Answer:  The O-H bond is more polar than the N-H because oxygen is more electronegative than nitrogen. Thus, alcohols form stronger hydrogen-bonds and have higher boiling points.

Diff: 2

Section:  19.4

 

35) Rank the following compounds in order of increasing boiling point (lowest to highest): triethylamine, cyclohexylamine, di-n-propylamine.

Answer:  triethylamine < di-n-propylamine < cyclohexylamine

Diff: 2

Section:  19.4

 

36) What common names for 1,4-butanediamine and 1,5-pentanediamine are derived from their characteristic pungent odors?

Answer:  putrescine and cadaverine

Diff: 3

Section:  19.4

 

37) If ethanol has a pKa value of 16, what is the pKb value of the ethoxide anion?

Answer:  -2

Diff: 2

Section:  19.5

38) Provide the product of the reaction shown below.

 

Answer:

Diff: 2

Section:  19.5

 

39) Which of the following amines is most basic?

  1. A) aniline
  2. B) N-ethylaniline
  3. C) N,N-diethylaniline
  4. D) piperidine
  5. E) pyrrole

Answer:  D

Diff: 2

Section:  19.6

 

 

40) Which of the following amines is the strongest base?

  1. A) cyclohexylamine
  2. B) pyrrole
  3. C) p-iodoaniline
  4. D) piperidine
  5. E) imidazole

Answer:  D

Diff: 2

Section:  19.6

 

41) Physostigmine is used in the treatment of glaucoma.  Within this structure, the atom indicated by __________ is most basic, while atom  __________ is least basic.

 

  1. A) 1 (most basic), 4 (least basic)
  2. B) 1 (most basic), 3 (least basic)
  3. C) 2 (most basic), 4 (least basic)
  4. D) 2 (most basic), 3 (least basic)
  5. E) None of the above

Answer:  A

Diff: 2

Section:  19.6

42) Since alkyl groups are electron donors, one might conclude that tertiary amines are much more basic than primary amines. Actually, primary and tertiary amines show similar ranges of basicity. Offer an explanation.

Answer:  While tertiary ammonium cations are stabilized to a greater degree by electron donation, they are larger and thus more poorly solvated.

Diff: 2

Section:  19.6

 

43) Circle the stronger base in the pair below, and briefly explain your choice.

 

Answer:  Cyclohexylamine is the stronger base. The lone pair electrons in aniline are delocalized into the adjacent aromatic π system.

Diff: 2

Section:  19.6

 

 

44) Circle the stronger base in the pair below, and briefly explain your choice.

 

Answer:  Pyrrolidine is the stronger base. Protonation of pyrrole results in loss of aromaticity.

Diff: 3

Section:  19.6

 

45) Circle the stronger base in the pair below, and briefly explain your choice.

 

Answer:  Diethylamine is the stronger base. The lone pair electrons in pyridine are in an sp2 orbital which is lower in energy than the sp3 orbital of the lone pair in diethylamine.

Diff: 3

Section:  19.6

 

46) A sample of cyclohexylamine is contaminated with considerable hydrocarbon impurity. How might the sample be purified using a technique based on solubility differences?

Answer:  Dissolve sample in ether. Wash with dilute HCl solution to convert the amine to the ammonium hydrochloride which is water soluble; hydrocarbon remains in ether. Neutralize the aqueous solution with base to reform the amine and extract with ether.

Diff: 2

Section:  19.7

47) In 1H NMR protons on the α-carbon of amines typically absorb between θ:

  1. A) 1.0 and 2.0 ppm
  2. B) 2.0 and 3.0 ppm
  3. C) 3.0 and 4.0 ppm
  4. D) 6.0 and 7.0 ppm
  5. E) 9.0 and 10.0 ppm

Answer:  B

Diff: 2

Section:  19.9

 

48) In the mass spectrum of dipropylamine, the base peak appears at m/z:

  1. A) 101
  2. B) 86
  3. C) 72
  4. D) 58
  5. E) none of the above

Answer:  C

Diff: 2

Section:  19.9

 

49) The α-carbon atom bonded to the nitrogen of an alkylamine usually appears in what chemical shift (δ) range?

  1. A) 5-20
  2. B) 30-50
  3. C) 80-100
  4. D) 120-150
  5. E) 180-220

Answer:  B

Diff: 2

Section:  19.9

 

50) A three-carbon, nitrogen-containing compound exhibits 3 13C NMR peaks (d 11.2, 27.3, and 44.9).  Which of the following compounds best matches this spectral data?

  1. A) H2NCH2CH2CH2OH
  2. B) (CH3)2CHNH2
  3. C) CH3NHCH2CH3
  4. D) CH3CH2CH2NH2
  5. E) CH3CH2C≡N

Answer:  D

Diff: 2

Section:  19.9

 

51) How might one distinguish a sample of trimethylamine from a sample of n-propylamine using IR spectroscopy?

Answer:  n-propylamine would show N-H stretches in the IR between 3200 and 3500 cm-1.

Diff: 2

Section:  19.9

52) How might the presence of an N-H functionally be indicated using NMR spectroscopy?

Answer:  Like the O-H group, the N-H group undergoes a rapid H exchange reaction with water. Adding D2O to the NMR sample would result in the disappearance of any peaks in the 1H NMR spectrum arising from N-H groups.

Diff: 2

Section:  19.9

 

53) How might one distinguish a sample of n-butylamine from a sample of diethylamine using IR spectroscopy?

Answer:  Primary amines, like n-butylamine, usually show two spikes in the N-H stretching region of the IR between 3200 and 3500 cm-1 while secondary amines usually show only one.

Diff: 3

Section:  19.9

 

 

54) When pentanal reacts with ethylamine under conditions of acid catalysis, the major organic product is __________.

  1. A) a ketone
  2. B) a nitrile
  3. C) an imine
  4. D) an oxime
  5. E) a hydrazone

Answer:  C

Diff: 2

Section:  19.10

 

55) When CH3CH2CHO reacts with PhNHNH2 under conditions of acid catalysis, the major organic product is __________.

  1. A) a ketone
  2. B) a nitrile
  3. C) an imine
  4. D) an oxime
  5. E) a hydrazone

Answer:  E

Diff: 2

Section:  19.10

56) Provide the structure of the major organic product in the reaction below.

 

Answer:

Diff: 2

Section:  19.10

 

 

57) Provide the structure of the major organic product in the reaction below.

 

Answer:

Diff: 2

Section:  19.10

 

58) When pyrrole undergoes electrophilic aromatic substitution, at which position does substitution occur?

  1. A) 2-position
  2. B) 3-position
  3. C) 4-position

Answer:  A

Diff: 2

Section:  19.11

 

59) Which of the following chloropyridines readily undergo nucleophilic substitution upon treatment with NaCN?

  1. A) 2-chloropyridine
  2. B) 3-chloropyridine
  3. C) 4-chloropyridine
  4. D) both A and C
  5. E) both A and B

Answer:  D

Diff: 2

Section:  19.11

60) Pyridine typically undergoes electrophilic aromatic substitution  __________  rapidly than benzene, and its preferred site of substitution is the  __________ – position.

  1. A) more, 2
  2. B) more, 3
  3. C) more, 4
  4. D) less, 2
  5. E) less, 3

Answer:  E

Diff: 2

Section:  19.11

 

 

61) When pyridine is treated with a mixture of nitric and sulfuric acids, the major product is:

  1. A) 2-nitropyridine
  2. B) 3-nitropyridine
  3. C) 4-nitropyridine
  4. D) 3-aminopyridine
  5. E) 4-aminopyridine

Answer:  B

Diff: 3

Section:  19.11

 

62) Which compound would react most rapidly with sodium methoxide and heat?

  1. A) chlorobenzene
  2. B) 2-chloropyridine
  3. C) 3-chloropyridine
  4. D) 3-chloropyrrole

Answer:  B

Diff: 3

Section:  19.11

 

63) Devise an efficient method for preparing p-nitrobenzoic acid from toluene.

Answer:

  1. HNO3, H2SO4
  2. Na2Cr2O7, H2SO4

Diff: 1

Section:  19.11

 

64) Provide the structure of the major organic product in the reaction below.

 

Answer:

Diff: 2

Section:  19.11

65) Why are strongly acidic reagents inappropriate when attempting an electrophilic aromatic substitution with aniline?

Answer:  Acidic reagents protonate the amino group transforming it from an activating group to a deactivating group.

Diff: 3

Section:  19.11

 

 

66) Pyridine does not undergo Friedel-Crafts reactions. Offer an explanation.

Answer:  The presence of the electronegative atom in the ring deactivates it toward reaction with electrophiles. In fact, the nitrogen lone pair tends to react with electropiles to produce an even further deactivated ring. It should also be noted that the nitrogen lone pair is in an orbital perpendicular to the ring’s π system and could not stabilize the intermediate carbocation in any event.

Diff: 3

Section:  19.11

 

67) Provide the major organic compound in the following reaction.

 

Answer:

Diff: 2

Section:  19.12

 

68) Provide the major organic product of the following reaction.

 

Answer:

Diff: 2

Section:  19.12

 

69) Provide the structure of the major organic product in the reaction below.

 

Answer:

Diff: 1

Section:  19.12

 

70) Can 2-methyl-2-butanamine be prepared in good yield from the reaction of ammonia with 2-bromo-2-methylbutane? Why or why not?

Answer:  No. SN2 reactions do not proceed with tertiary substrates.

Diff: 2

Section:  19.12

 

71) Can 1-hexanamine be prepared in good yield from the reaction of a 1:1 molar ratio of ammonia and 1-bromohexane? Why or why not?

Answer:  No. Problems with multiple alkylation exist.

Diff: 2

Section:  19.12

 

72) Which of the following is an intermediate in the mechanism for amide synthesis through acylation of an amine?

 

  1. A)
  2. B)
  3. C)
  4. D)

Answer:  D

Diff: 2

Section:  19.13

 

73) Provide the major organic product of the following reaction.

 

Answer:

Diff: 2

Section:  19.13

 

74) Draw a structure for the expected product of the following reaction.

 

 

 

 

Answer:

 

 

Diff: 3

Section:  19.13

 

75) Provide the structure of the major organic product in the reaction below.

 

Answer:

Diff: 2

Section:  19.13

 

76) Provide a detailed, stepwise mechanism for the reaction of acetyl chloride with n-propylamine.

Answer:

Diff: 3

Section:  19.13

 

77) When a 1° amine reacts with an alkyl sulfonyl chloride, the major organic product is __________.

  1. A) a tosylhydrazone
  2. B) a nitrile
  3. C) a sulfoxide
  4. D) an oxime
  5. E) a sulfonamide

Answer:  E

Diff: 2

Section:  19.14

 

78) The Hofmann elimination proceeds via a(n) __________ pathway.

  1. A) E2
  2. B) E1
  3. C) SN1
  4. D) SN2
  5. E) none of the above

Answer:  A

Diff: 1

Section:  19.15

 

79) Provide the structure of the major organic product in the reaction below.

 

Answer:

Diff: 2

Section:  19.15

 

80) Provide the major organic product of the following reaction.

 

Answer:

Diff: 2

Section:  19.15

 

81) Compound A, C9H17N, is an optically inactive alkaloid, containing a tertiary amine that is not located at the bridgehead of the structures fused bicyclic ring system.  Exhaustive alkylation of A with methyl iodide, followed by a Hofmann elimination reaction resulted in a racemic mixture of chiral tertiary amine products B, C10H19N.  Provide a structure for A and one of the enantiomeric products B.

Answer:

 

Diff: 3

Section:  19.15

 

82) Provide the structure of the major organic product in the reaction below.

 

Answer:

Diff: 2

Section:  19.15

 

83) Provide the structure of the major organic product in the reaction below.

 

Answer:

Diff: 3

Section:  19.15

 

84) Heating a(n) __________ results in a Cope elimination.

  1. A) amine oxide
  2. B) imine
  3. C) enamine
  4. D) oxime
  5. E) quaternary ammonium salt

Answer:  A

Diff: 1

Section:  19.16

 

85) Provide the structure of the major organic product in the reaction below.

 

Answer:

Diff: 3

Section:  19.16

 

86) Provide the structure of the major organic product in the reaction below.

 

Answer:

Diff: 2

Section:  19.16

 

87) Secondary amines react with the nitrosonium ion to generate:

  1. A) diazonium salts
  2. B) oximes
  3. C) N-nitrosoamines
  4. D) imines
  5. E) anilines

Answer:  C

Diff: 2

Section:  19.17

 

 

88) Provide the formula for nitrous acid.

Answer:  HNO2

Diff: 1

Section:  19.17

89) Provide the structure of the major organic product in the reaction below.

 

Answer:

Diff: 1

Section:  19.18

 

90) Devise an efficient method for preparing fluorobenzene from benzene.

Answer:

  1. HNO3, H2SO4
  2. Fe, HCl
  3. -OH
  4. NaNO2, HCl
  5. HBF4

Diff: 2

Section:  19.18

 

 

91) Provide the major organic compound in the following reaction.

 

Answer:

Diff: 2

Section:  19.18

92) Provide the major organic compound in the following reaction.

Answer:

Diff: 2

Section:  19.18

 

 

93) Provide the major organic product of the following reaction.

 

Answer:

Diff: 2

Section:  19.18

94) What sequence of reagents can be used to carry out the transformation shown below?

 

Answer:  1.  NaNO2, HCl   2.  CuBr

Diff: 2

Section:  19.18

 

95) Complete the following reaction by filling in the necessary reagents.

 

 

Answer:

 

Diff: 3

Section:  19.18

 

 

96) Provide the structure of the major organic product in the reaction below.

 

Answer:

Diff: 2

Section:  19.18

97) Provide the structure of the major organic product in the reaction below.

 

Answer:

Diff: 2

Section:  19.18

 

98) Devise an efficient method for preparing 4-bromobenzonitrile from benzene.

Answer:

  1. Br2, FeBr3
  2. HNO3, H2SO4
  3. Sn, HCl
  4. H2SO4, NaNO2
  5. CuCN

Diff: 2

Section:  19.18

 

99) Devise an efficient method for preparing m-cresol from m-toluidine.

Answer:  1. NaNO2, HCl

  1. H3O+

Diff: 2

Section:  19.18

 

 

100) Devise an efficient method for preparing 3-bromotoluene from toluene.

Answer:

  1. HNO3, H2SO4
  2. Sn, HCl
  3. CH3COCl
  4. Br2, FeBr3
  5. H3O+
  6. H2SO4, NaNO2
  7. H3PO2

Diff: 3

Section:  19.18

101) Which of the following amines could be formed by reduction of an amide?

 

1) benzylamine     2) isopropylamine     3) aniline     4) triethylamine

  1. A) 1
  2. B) 3 and 4
  3. C) 1 and 4
  4. D) 2 and 3
  5. E) 1, 3 and 4

Answer:  C

Diff: 3

Section:  19.19

 

102) Provide the major organic product of the following reaction.

 

Answer:

Diff: 2

Section:  19.19

 

 

103) Provide the major organic product of the following reaction.

 

Answer:

Diff: 2

Section:  19.19

 

104) Devise an efficient method for preparing ethylisopropylamine from ethylamine.

Answer:  CH3COCH3, NaBH3CN

Diff: 2

Section:  19.19

105) The final product is a derivative of Amonafide, a drug used to treat breast cancer (J. Med. Chem. 2007, 4122).  Complete each step of the synthesis by filling in the necessary reagents.

 

 

Answer:

 

 

Diff: 3

Section:  19.20

 

 

106) Provide the major organic product of the following reaction.

 

Answer:

Diff: 2

Section:  19.21

 

107) Complete the short synthesis below by providing the necessary reagents.

 

 

Answer:  1) NaNO2 / HCl     2) CuCN     3) LiAlH4 or H2 / Pd

Diff: 3

Section:  19.21

108) Devise an efficient method for preparing 1-pentanamine from 1-chloropentane.

Answer:

  1. phthalimide anion
  2. H2NNH2, heat

or

  1. NaN3
  2. LiAlH4or H2, Pd

Diff: 1

Section:  19.21

 

109) Devise an efficient method for preparing 2-phenylethanamine from 2-phenylethanol.

Answer:

  1. PCC
  2. H2NOH
  3. H2, Ni or LiAlH4

or

  1. SOCl2
  2. NaN3
  3. LiAlH4or H2, Pd

Diff: 1

Section:  19.21

 

 

110) Provide the structure of the major organic product in the reaction below.

 

Answer:

Diff: 2

Section:  19.21

 

111) Provide the structure of the major organic product in the reaction below.

 

Answer:

Diff: 2

Section:  19.21

112) Devise an efficient method for preparing 1-pentanamine from but-1-ene.

Answer:

  1. HBr, ROOR
  2. NaCN
  3. LiAlH4

Diff: 2

Section:  19.21

 

113) Devise an efficient method for preparing cyclohexylamine from cyclohexylmethanol.

Answer:

  1. Na2Cr2O7, H2SO4
  2. SOCl2
  3. NH3
  4. Br2, NaOH

Diff: 3

Section:  19.21

 

 

114) Devise an efficient method for preparing 1,4-diaminobutane from cyclohexene.

Answer:

  1. KMnO4
  2. SOCl2
  3. NH3
  4. Br2, NaOH

Diff: 3

Section:  19.21