Structures

Question 1

R-CH2OH

Answer 1

primary alcohol

Question 1

R-COOH

Answer 1

Carboxylic acid

Question 2

RCHO

Answer 2

aldehyde

Question 3

ADH

Answer 3

alcohol dehydrogenase

catalyzes conversion of primary alcohol to aldehyde AND secondary alcohol to ketone

bulk in cytosol

Question 4

is further oxidation of ketone possible

Answer 4

NO - dont have hydrogen

Question 5

ALDH

Answer 5

aldehyde dehydrogenase

catalyzes conversion of aldehyde to corresponding carboxylic acid (irreversible)

bulk of ALDH is in mitochondria

Question 6

CH2O

Answer 6

formaldehyde

Question 7

CH3CHO

Answer 7

acetaldehyde

Question 8

benzene ring with a + charge N connected to - charge O

Answer 8

N-oxide

formed from the oxidation of pyridine and other tertiary amines

Question 9

pyridine is a ___ ___

Answer 9

tertiary amine

Question 10

R-C(=O)-NR’R”

Answer 10

amide (carboxamide)

Question 11

what is a dialkyl amide

Answer 11

amide with 2 alkyl groups bonded to the N

SLOW reaction
if 2 alpha carbons, either one can come off

Question 12

Ether

Answer 12

R-O-R’

Question 13

thioether

Answer 13

R-S-R’

Question 14

what reaction produces a hemiacetal intermediate

Answer 14

O-dealkylation

Question 15

RR’COR

Answer 15

HEMI ACETAL

carbon connected to 1 ether oxygen + 3 other substituents

VERY UNSTABLE

Question 16

R-S-R what reaction does it undergo

Answer 16

sulfoxidation
(if 1 R group is methyl it’s a different story)

Question 17

sulfide

Answer 17

R-S-R (also thioether)

Question 18

sulfoxide

Answer 18

S=O (2 R groups on S)

Question 19

sulfone

Answer 19

O=S=O (2 R groups on S

Question 20

hemithioacetal

Answer 20

carbon connected to Sulfur that’s part of a thioether bond, and OH, plus 2 other substituents

Question 21

carbinolamine

Answer 21

metabolically unstable intermediate formed in O-deamination and N-dealkylation

carbon with an amine and hydroxyl group (+2 R’s)

Question 22

cyano group

Answer 22

C triple bond N

Question 23

acetonitrile

Answer 23

CH3-C triple bond N

1 of only cyano groups allowed in drug molecules because it is hydrophilic enough to be readily excreted

Question 24

"ketene"

Answer 24

=C= formed in the oxidation of carbon-carbon triple bonds reacts with h2o to produce corresponding carboxylic acid

Question 25

aniline

Answer 25

benzene ring with NH2 as the only substituent likely to undergo N-hydroxylation

Question 26

Nitrenium ion

Answer 26

AR-N+-H produced in N-hydroxylation of AR-NH2 if the aromatic ring is 2 or more fused rings. there is enough stability for nitrenium ion to be there POTENT CARCINOGEN

Question 27

nitroso

Answer 27

R-N=O produced in the reduction of aromatic nitro compounds (from nitro radical) this can only be done in the GI tract

Question 28

hydroxylamine

Answer 28

amineattached to hydroxyl produced from the reduction of nitroso (can only be done by the microorganisms in the GI tract)

Question 29

nitrate

Answer 29

NO3- NO DIRECT HYDROLYSIS. must be converted to nitrite

Question 30

nitrite

Answer 30

NO2- O=N-O-

Question 31

hydrazide group

Answer 31

N-N

Question 32

name the amides that can be hydrolyzed

Answer 32

open chain cyclic hydrazides urea type

Question 33

which open chain amides can be hydrolyzed?

Answer 33

primary and secondary amides

Question 34

which cyclic amides can be hydrolyzed?

Answer 34

imides and lactams

Question 35

give an example of an imide and a lactam what reaction can they undergo?

Answer 35

lactam - penicillin imide - phthalidone they are cyclic amides that undergo HYDROLYSIS

Question 36

Nam a hydrazide that undergoes hydrolysis and explain the significance

Answer 36

isoniazid undergoes hydrolysis to produce a metabolite that is TOXIC to the liver further oxidized to carbocation/radical species

Question 37

where is a thiourea clipped when it undergoes hydrolysis? name a thiourea

Answer 37

chloropropamide clipped between NH and carbonyl

Question 38

which has more predictable hydrolysis - open chain urea or cyclic urea?

Answer 38

open chain is more predictable

Question 39

name 2 cyclic ureas

Answer 39

barbiturates - STABLE TO HYDROLYSIS 5-phenylhydantoin

Question 40

explain how cyclic ureas undergo less predictable hydrolysis than open chain

Answer 40

5-phenylhydantoin is a cyclic urea that undergoes hydrolysis the barbiturates are cyclic ureas that do NOT undergo hydrolysis - stable to hydrolysis

Question 41

what is cyclamate

Answer 41

was almost introduced as a substitute for table sugar, but produces a carcinogen upon hydrolysis by gut bacterial enzymes

Question 42

carbamates undergo hydrolysis to produce....

Answer 42

alcohol, carbon dioxide, and amine

Question 43

acrolein

Answer 43

michael acceptor generated from the metabolism (oxidation) of cyclophosphamide