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15-17 Flashcards

1
Q

Stereoisomers that are nonsuperposable mirror
images

A

Enantiomers

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2
Q

Greek cheir

A

“hand”

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2
Q

an object that is not superposable on its mirror image

A

Chiral

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2
Q

most common cause of enantiomerism in organic molecules is the

A

presence of a carbon with four different groups bonded to it

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2
Q

A mixture of equal amounts of two enantiomers

A

Racemic mixture

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2
Q

“a cluster of grapes”

A

racemus,

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2
Q

A tetrahedral carbon atom that has four
different groups bonded to it

A

Stereocenter

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2
Q

An object that lacks chirality; an object that is
superposable on its mirror image

A

Achiral

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3
Q

when the lowest-priority group is away from you the
order of priority of groups on a stereocenter is clockwise

A

R

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3
Q

Showing that a compound rotates the plane
of polarized light

A

Optically active

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3
Q

Stereoisomers that are not mirror images

A

Diastereomers

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3
Q

when the lowest-priority group is away from you, the
order of priority of groups on a stereocenter is counterclockwise

A

S

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3
Q

A set of rules for specifying the configuration about
a stereocenter

A

R,S system

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3
Q

“straight

A

rectus

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3
Q

very effective for the treatment of high blood pressure and congestive heart failure

A

Captopril

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3
Q

The counterclockwise (to the left) rotation of the plane of polarized light in a polarimeter

A

Levorotatory

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3
Q

The clockwise (to the right) rotation of the plane
of polarized light in a polarimeter

A

Dextrorotatory

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4
Q

“left”

A

sinister

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4
Q

Light with waves vibrating in only parallel planes

A

Plane-polarized light

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4
Q

The (1) enantiomer of lactic acid is produced by

A

muscle tissue in humans

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4
Q

n stereocenters, the maximum number of stereoisomers possible is

A

2^n

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4
Q

number of degrees by which an optically active compound rotates the plane of polarized light is called its

A

specific rotation

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4
Q

Chymotrypsin has ___ stereocenters

A

251

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4
Q

The (2) enantiomer is found in

A

sour cream and sour milk

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4
Q

an enzyme in the intestines of animals that catalyzes the digestion of proteins

A

Chymotrypsin

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4
Q

enzyme catalyzes a biological reaction of a molecule by first positioning the molecule at a

A

binding site

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4
Q

powerful stimulants of the central nervous system

A

Amphetamine, methamphetamine, and phentermine

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4
Q

to measure optical activity

A

polarimeter

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4
Q

e sulfate salt of amphetamine is prescribed as

A

Benzedrine

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4
Q

e hydrochloride salt of phentermine aS

A

Fastin

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5
Q

amphetamines have in common a

A

a benzene ring with a three-carbon side chain and an amine nitrogen on the second carbon of the side chain

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5
Q

hydrochloride salt of the S enantiomer of methamphetamine as

A

Methedrine

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5
Q

these compounds are alkali-like

A

Alkaloids

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5
Q

action of amphetamines is similar to that of

A

epinephrine

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5
Q

Abuse of amphetamines

A

drugs are addictive, concentrate in the brain and nervous system, and can lead to long periods of sleeplessness, loss of weight, and paranoia

5
Q

“poison hemlock used in the death of Socrates

A

s- Coniine

5
Q

amphetamines share an ability to

A

reduce fatigue and diminish hunger by raising the glucose level of the blood

5
Q

prescribed to counter mild depression, reduce hyperactivity in children, and suppress appetite in people who are trying to lose weight

A

amphetamines

5
Q

s the toxic principle of water hemlock

A
6
Q

hydrochloride salt of epinephrine

A

Adrenalin

6
Q

An amine in which nitrogen is bonded only
to alkyl groups

A

Aliphatic amine

6
Q

An amine in which nitrogen is one of the atoms
of a ring

A

Heterocyclic amine

6
Q

An amine in which nitrogen is bonded to one
or more aromatic rings

A

Aromatic amine

7
Q

An amine in which nitrogen is one of the atoms of an aromatic ring

A

Heterocyclic aromatic amine

7
Q

occurs in the tobacco plant

A

S)-Nicotine

8
Q

basic nitrogen-containing compounds found in the
roots, bark, leaves, berries, or fruits of plants

A

Alkaloids

8
Q

retains the bronchodilating effects of epinephrine but is free from its cardiac-stimulating effects

A

isoproterenol

9
Q

Cocaine is a central nervous system stimulant obtained from

A

the leaves of the coca plant

9
Q

first modern tranquilizers were

A

derivatives of a compound called benzodiazepine

9
Q

Librium

A

chlorodiazepoxide 1960

9
Q

Valium

A

Diazepam

9
Q

an important treatment of asthma and hay fever

A

epinephrine

9
Q

Epinephrine is commonly referred to as a

A

catecholamine

9
Q

Epinephrine was first isolated in pure form in

A

1897

9
Q

One of the most important of the first synthetic catecholamines

A

isoproterenol

9
Q

problem with the first synthetic catecholamines

A

they are inactivated by an enzyme-catalyzed reaction that converts one of the OH groups on the catechol unit to an OCH3 group

9
Q

Epinephrine occurs in the

A

adrenal gland

9
Q

hydrochloride salt of (S)-isoproterenol is a

A

nasal decongestant

9
Q

reason for preparing these and other amine drugs as salts

A

very susceptible to oxidation and decomposition by atmospheric oxygen, with a corresponding loss of biological activity

9
Q

Brethaire

A

terbutaline

10
Q

from violets

A

beta–Ionone

10
Q

the commercially most successful of the antiasthma medications

A

albuterol

10
Q

functional group of an aldehyde

A

a carbonyl group bonded to a hydrogen atom

10
Q

R enantiomer of albuterol is ___ times more
effective in the treatment of asthma than the S enantiomer

A

68

10
Q

Naturally Occurring Aldehydes and Ketones

A

Benzaldehyde
Cinnamaldehyde
Citronellal
Muscone
Vanillin
beta–Ionone

10
Q

oil of cinnamon

A

Cinnamaldehyde

10
Q

functional group of a ketone

A

is a carbonyl group bonded to two carbon atoms

10
Q

oil of almonds

A

Benzaldehyde

10
Q

citronella oils; also in
lemon and lemon grass oils

A

Citronellal

10
Q

(vanilla bean)

A

Vanillin

10
Q

from the musk deer;
used in perfumes

A

Muscone

10
Q

methyl ethyl ketone

A

2-Butanone

11
Q

used as a solvent for paints
and varnishes.

A

methyl ethyl ketone (MEK)

12
Q

to distinguish between ketone and aldehyde

A

by oxidation since aldehyde is easy to oxidize and ketone are not easy to oxidize

12
Q

Aldehydes are oxidized to

A

carboxylic acids

13
Q

Tollens’ reagent

A

contains silver nitrate and ammonia in water.

14
Q

silver-mirror test

A

solution is added to an aldehyde, the aldehyde acts as a reducing agent and reduces the complexed silver ion to silver metal

15
Q

rarely used for the oxidation of aldehydes because of its high cost and because of the availability of other

A

silver(I)

15
Q

double bond of an alkene can be reduced by hydrogen in the presence of a

A

transition metal catalyst

16
Q

advantage of using NaBH4 over the H2/metal reduction is that

A

NaBH4 does not reduce carbon–carbon double bonds

16
Q

most commonly used in the laboratory for the reduction of an aldehyde or ketone is

A

sodium borohydride

16
Q

A molecule containing a carbon bonded to one OH
group and one OR group; the product of adding one molecule of alcohol to the carbonyl group of an aldehyde or ketone

A

Hemiacetal

17
Q

Constitutional isomers that differ in the location of a
hydrogen atom and a double bond relative to an O or N atom

A

Tautomers

17
Q

A molecule containing two OR groups bonded to the same carbon

A

Acetal

17
Q

A molecule containing an OH group bonded to a carbon of a carbon–carbon double bond

A

Enol

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