O Chem 19 Flashcards


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1

Which of the following is not an alkaloid?

A) Cocaine
B) Mesitylene
C) Nicotine
D) Mescaline
E) Morphine

B) Mesitylene

2

Sec-Butylamine is the common name of what compound?

A) 1-butanamine
B) 2-butanamine
C) N-methyl-1-propanamine
D) N-methyl-2-propanamine
E) N-ethylethanamine

B) 2- butanamine

3

Identify the correct systematic name for the following compound?

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

C) 3-(diethylamino)cyclohex-3-enol

4

Provide the correct IUPAC name for the following amine?

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

C) 4,N-dimethyl-4-penten-2-amine

5

Identify the correct name for the following structure?

A) 5-methyl-4-methylaminocyclohept-5-enol
B) 5-hydroxy-2,N-dimethylcyclohept-2-enamine
C) 4-hydroxy-7,N-dimethylcyclohept-6-enamine
D) 4-methyl-5-methylaminocyclohept-3-enol

A) 5-methyl-4-methylaminocyclohept-5-enol

6

Which of the following is a tertiary amine?

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

D) N,N-dimethylaniline

7

Which of the following is a secondary amine?

A) Cyclohexylamine
B) 3-pentamine
C) methylamine
D) N,N-dimethylaniline
E) N-ethyl-1-propanamine

E) N-ethyl-1-propanamine

8

Which of the following amines is most soluble in water?

A) pyrrolidine
B) PhNH2
C) (CH3)3N
D) (CH3CH2CH2)2NH
E) Ethylamine

E) Ethylamine

9

Which of the following compounds is a secondary amine?

A) Cyclohexylamine
B) t-butylamine
C) N-ethylaniline
D) N,N-diethylaniline
E) N-butylpyridinium bromide

C) N-ethylaniline

10

Which of the following amines can be resolved into enantiomers?

A) Trimethylamine
B) 3-pentanamine
C) 2-pentanamine
D) dimethylammonium chloride
E) 4-(dimethylamino) pyridine

C) 2-pentanamine

11

The Nitrogen atome of trimethylamine is ______ hybridized which is reflected in the CNC bond angle _____

A) sp, 180
B) Sp2, 120
C) Sp2, 108
D) sp3, 120
E) sp3, 108

E) sp3, 108

12

The Nitrogen's lone pair in pyrrolidine is best described as occupying which type of orbital?

A) S
B) Sp3
C) sp2
D) sp
E) P

B) Sp3

13

Which of the following compounds contains a tertiary amine?

1) 2-methyl-2-propanamine
2) N-ethylpyrrolidine
3) N-methylcyclohexylamine
4) 2-(dimethylamino)butanal

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

D) 2 and 4

14

Why cant N-methyl-2-propanamine be resolved into isolable enantiomers even though the compound is chiral?

Enantiomers interconvert rapidly vis nitrogen inversion

15

The following structure has been used in monitoring the development of amyloid plaques in Alzheimers patients. Which sequences correctly ranks the following nitrogens in order of increasing Pkb value?

A)2<3<1 B) 3<2<1 C) 2<1<3 D) 1<3<2

A) 2<3<1

16

Which of the following amines is most basic?

A) Aniline
B) N-ethylanline
C) N,N-diethylaniline
D) piperidine
E) pyrrole

D) piperidine

17

Which of the following amines is the strongest base?

A) cyclohexylamine
B) pyrrole
C) p-iodoaniline
D) piperidine
E) imidazole

D) piperidine

18

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

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

A) 1 (most basic), 4 (least basic)

19

In 1H NMR protons on the alpha- Carbon of amines typically absorb between theta.

A) 1.0 and 2.0 ppm
B) 2.0 and 3.0 ppm
C) 3.0 and 4.0 ppm
D) 6.0 and 7.0 ppm
E) 9.0 and 10.0 ppm

B) 2.0 and 3.0 ppm

20

In the mass spectrum of dipropylamine, the base peak appears at m/z ______

A) 101
B) 86
C) 72
D) 58
E) none of the above

C) 72

21

The alpha- Carbon atome bonded to the Nitrogen of an alkylamine usually appears in what chemical shift range?

A) 5-20
B) 30-50
C) 80-100
D) 120-150
E) 180-220

B) 30-50

22

A three Carbon, Nitrogen-containing compound exhibits 3 13c NMR peaks ( 11.2, 27.3, 44.9) Which of the following compounds best matches the spectral data?

A) H2NCH2Ch2CH2OH
B) CH3NHCH2CH3
C) CH3NHCH2CH3
D) CH3CH2CH2NH2
E) Ch3Ch2C-N

D) Ch3Ch2Ch2Nh2

23

When pentanal reacts with ethylamine under conditions of acid catalysis, the major organic product is ____

A) A ketone
B) A nitrile
C) An imine
D) An oxime
E) A hydrazone

C) An imine

24

When Ch3Ch2ChO reacts with PhNhNh2 under conditions of acid catalysis, the major organic product is _____

A) a ketone
B) a nitrile
C) an imine
D) an oxime
E) a hydrazone

E) a hydrazone

25

When pyrrole undergoes EAS at which position does substitution occur?

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

A) 2- position

26

Which of the following chloropyridines readily undergo NAS upon treatment with NaCN?

A) 2-chloropyridine
B) 3-chloropyridine
C) 4-chloropyridine
D) Both A and C
E) Both A and B

D) Both A and C

27

Pyridine typically undergoes EAS _____ rapidly than benzene, and its preferred site of substitution is the ________ - position

A) More, 2
B) More, 3
C) More, 4
D) Less, 2
E) less, 3

E) Less, 3

28

When pyridine is treated with a mixture of Nitric and Sulfuric acids, the major product is:

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

B) 3-nitropyridine

29

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

A) chlorobenzene
B) 2-chloropyridine
C) 3-chloropyridine
D) 3-chloropyrrole

B) 2-chloropyridine

30

Which compound results from the reaction below?

A) imine
B) amide
C) primary amine
D) quaternary ammonium salt
E) nitrous acid

D) quaternary ammonium salt

31

When a Primary amine reacts with an alkyl sulfonyl chloride, the major organic product is ______

A) a todylhydrazone
B) a nitrile
C) a sulfoxide
D) an oxime
E) a sulfonamide

E) A sulfonamide

32

The Hofmann eliminations proceeds via a ______ pathway?

A) E2
B) E1
C) SN1
D) SN2
E) None of the Above

A) E2

33

Heating a(n)_____ results in Cope elimination
A) amine oxide
B) imine
C) enamine
D) oxime
E) Quaternary Ammonium salt

A) amine oxide

34

Secondary amines react with the nitrosonium ion to generate:

A) diazonium salts
B) oximes
C) N-nitrosoamines
D) Imines
E) anilines

C) N-nitrosoamines

35

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

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

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

C) 1 and 4

36

Which of the following would be the best phase transfer catalyst?

A) N(Ch3)4I
B) N((CH2)5Ch3)4 I
C) Nh4BR
D) N((Ch2)3Ch3)3

B) N((Ch2)5Ch3)4I