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Organic Chem > Ch4 > Flashcards

Ch4 Flashcards

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1
Q

two types of isomers

A

constitutional isomer, stereoisomers

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2
Q

Constitutional isomer

A

differ int he way their atoms are connected / connected differently

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3
Q

stereoisomer

A

connected in the same way, differ in the way their atoms are arranged in space.

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4
Q

two kinds of stereoisomer

A

conformational isomers and configurational isomers.

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5
Q

conformational isomers

A

conformers/ stereoisomers that rapidly interconvert at room temperature, because they interconvert they cannot be separated

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6
Q

configurational isomers

A

stereoisomers that cannot interconvert unless covalent bonds are broken, because they cannot interconvert configurational isomers can be separated.

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7
Q

two kinds of conformational isomer

A

rotation about carbon-carbon single bonds/ amine inversion

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8
Q

two kinds of configurational isomers

A

cis-trans isomers, and isomers that contain asymmetric centers

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9
Q

other name of the cis-trans isomers

A

geometric isomer

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10
Q

the ____ isomer has its substituents on the same side of the ring; the ____ isomer has its substituents on opposite sides of the ring

A

cis, trans

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11
Q

rotation about a double bond occurs only when?

A

only if the pi bond breaks

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12
Q

the compound with the hydrogens on the same side of the double bond is called the ____ isomer

A

cis

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13
Q

the compound with the hydrogens on the opposite side of the double bond is called the ____ isomer

A

trans

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14
Q

cis and trans isomers have the same molecular formula and the same bonds but have different _______ they differ in the way their atoms are oriented in space

A

configurations

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15
Q

if one of the sp^2 carbons is attached to two identical substituents, then the compound cannot have ________________

A

cis and trans isomers

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16
Q

cis and trans isomers can be separated from each other because they are different compounds with different______

A

physical properties

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17
Q

____________ is used to name alkenes that do not have a hydrogen attached to each of the sp^2 carbons

A

E,Z system

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18
Q

Z isomer

A

has the high-priority groups on the same side of the double bond

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19
Q

E isomer

A

has the high-priority groups on opposite sides of the double bond

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20
Q

object with a right-handed and a left-handed form is said to be ?

A

chiral

21
Q

a chiral object has a

A

nonsuperimposable mirror image, in other words its mirror image does not look the same as an image of the object itself.

22
Q

objects that are not chiral are said to be?

A

achiral, an achiral object has a superimposable mirror image

23
Q

______________ is an atom bonded to four different groups.

A

asymmetric center

24
Q

a compound with one asymmetric center can exist as

A

two stereoisomers

25
Q

molecules that are nonsuperimposable mirror images of each other are called?

A

enantiomers

26
Q

asymmetric center is also called?

A

stereocenter, stereogenic center however, stereocenter is an atom at which the interchange of two groups produces a stereoisomer, thus stereocenters include both asymmetric centers and the sp^2 carbons of an alkene or the sp^3 carbons of a cyclic compound, where the interchange of two groups converts a cis isomer to a trans isomer or vice versa.

27
Q

although all _________ are stereocenters, not all stereocenters are _________

A

asymmetric center

28
Q

a system of nomenclature for enantiomer pairs

A

R configuration and S configuration

29
Q

R configuration _____________arrow, S configuration ______________arrow

A

clockwise, counterclockwise

30
Q

Enantiomers share many of the same properties, including the same bp, melting point, solubilities except those that stem from _________________________

A

how the groups bonded to the asymmetric center are arranged in space / Eg: the way they interact with plane-polarized light

31
Q

when plane-polarized light passes through a solution of achiral molecules, the light emerges from the solution with its plane of polarization _______

A

unchanged

32
Q

when plane-polarized light passes through a solution of chiral molecules, the light emerges from the solution with its plane of polarization _______

A

rotated either clockwise or counterclockwise

33
Q

a compound that rotates the plane of polarization of plane-polarized light is said to be ______

A

optically active

34
Q

achiral compounds are optically ?

A

inactive

35
Q

if an optically active compound rotates the plane of polarization clockwise, then the compound is said to be?

A

dextrorotatory( indicated by +)

36
Q

if an optically active compound rotates the plane of polarization counterclockwise, then the compound is said to be?

A

levorotatory( indicated by -)

37
Q

the direction and amount an optically active compound rotates the plane of polarization of plane- polarized light can be measured with an instrument called?

A

polarimeter

38
Q

observed rotation is dependent on

A

concentration of the sample, and the length of the sample tube, the rotation also depends on the temperature and the wavelength of the light source

39
Q

if one enantiomer has a specific rotation of +5.75 the other has?

A

-5.75

40
Q

racemic mixture or racemate

A

a mixture of equal amounts of two enantiomers

41
Q

racemic mixtures are optically _____

A

inactive, because for every molecule in a racemic mixture that rotates the plane of polarization in one direction, there is a mirror-image molecule that rotates the plane in the opposite direction.

42
Q

the enantiomeric excess also called the optical purity tells us?

A

how much of an excess of one enantiomer is in the mixture

43
Q

if we know the number of asymmetric centers we can calculate?

A

the maximum number of stereoisomers for that compound: a compound can have a maximum of 2^n stereoisomers

44
Q

diastereomers

A

stereoisomers that are not identical and not mirror images of each other

45
Q

when fischer projections are drawn for stereoisomers with two adjacent asymmetric centers, the enantiomers with the hydrogens on the same side of the carbon chain are called the? , whereas those with the hydrogens on opposite sides are called the?

A

erythro enantiomers/ threo enantiomers

46
Q

enatiomers have _____ physical properties and chemical properties whereas diastereomers are

A

identical, different

47
Q

if one of the four groups attached to nitrogen is a lone pair, the enantiomers cannot be separated because they interconvert rapidly at room temperature. this rapid interconversion is called?

A

amine inversion

48
Q

enantiomers can be separated by a technique called

A

chromatography

49
Q

chiral probe

A

something capable of distinguishing between enantiomers.

Organic Chem (4 decks)

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