O Chem 19 Flashcards

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Which of the following is not an alkaloid?

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

B) Mesitylene


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


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


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


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


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


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


Which of the following amines is most soluble in water?

A) pyrrolidine
B) PhNH2
C) (CH3)3N
E) Ethylamine

E) Ethylamine


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


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


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


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


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


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

Enantiomers interconvert rapidly vis nitrogen inversion


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


Which of the following amines is most basic?

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

D) piperidine


Which of the following amines is the strongest base?

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

D) piperidine


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)


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


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


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


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?

E) Ch3Ch2C-N

D) Ch3Ch2Ch2Nh2


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


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


When pyrrole undergoes EAS at which position does substitution occur?

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

A) 2- position


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


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


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


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


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


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


The Hofmann eliminations proceeds via a ______ pathway?

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

A) E2


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

A) amine oxide


Secondary amines react with the nitrosonium ion to generate:

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

C) N-nitrosoamines


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


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