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Organic Chemistry > Orgo Exam 2 > Flashcards

Orgo Exam 2 Flashcards

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1
Q

same connectivity, but different in terms of geometry

A

stereoisomer

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2
Q

different compound with same connectivity but not mirror images

A

diastereomers

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3
Q

physical properties of diastereomers

A

have different physical properties

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4
Q

non-superimposable mirror image

A

enantiomer

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5
Q

physical properties of enantiomers

A

they have the same properties except they rotate polarized light in opposite directions

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6
Q

cant interconvert, must have 4 different groups

A

chiral atoms

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7
Q

clockwise

A

R

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8
Q

counterclockwise

A

S

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9
Q

are neutral amines chiral?

A

if amines are trapped in a ring structure, they are chiral

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10
Q

are conformational isomers chiral?

A

most aren’t but a few are. If it can inner convert easily, it is not chiral

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11
Q

restricted rotation around a single bond

A

atropisomer

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12
Q

max number of possible enantiomers

A

2^n where n is the number of chiral centers

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13
Q

achiral compounds with chiral centers

A

meso compounds

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14
Q

two ways to distinguish enantiomers

A
  1. chiral interactions (analogous to hand in glove)

2. rotation of plane polarized light

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15
Q

a 50/50 mixture of enantiomers

A

racemic

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16
Q

bronsted acid

A

proton donor

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17
Q

bronsted base

A

proton acceptor

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18
Q

high pka, — acidic

A

less

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19
Q

which side does an acid/base reaction favor?

A

going to favor side with weaker acid/ side with most stable conjugate base

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20
Q

lewis acid

A

electron pair acceptor

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21
Q

lewis base

A

electron pair donor

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22
Q

electrophile

A

lewis acid

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23
Q

nucleophile

A

lewis base

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24
Q

tries to form a bond with something other than hydrogen

A

nucleophile

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25
Q

when forward and reverse reaction rates are equal

A

equilibrium

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26
Q

How much energy is required to make a system do something

A

changeGprime — gibbs free energy

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27
Q

as k increases, change G —

A

decreases

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28
Q

-changeG favors

A

products

29
Q

energy of forming or braking bonds

A

enthalpy- changeH

30
Q

entropy

A

changeS

31
Q

-changeH favors — changeG

is this exothermic or endothermic?

A

-

exothermic

32
Q

+change favors —changeG

exo or endo?

A

+

endothermic

33
Q

+changeS favors —changeG

A

-

34
Q

-changeS favors — changeG

A

+

35
Q

— take priority over halide for determining main chain

A

alcohols

36
Q

number through alkenes must have the — number

A

lowest

37
Q

main chain contains groups that are facing the same direction

A

cis isomer

38
Q

main chain contains groups that are facing opposite directions

A

trans isomers

39
Q

E

A

trans

40
Q

Z

A

cis

41
Q

atropisomers are only chiral when…

A

the rotation barrier is high enough (cant rotate all the way around)

42
Q

kcal to rotate around a single bond

A

6

43
Q

kcal to rotate around a double bond

A

35

44
Q

kcal to rotate atropisomer

A

greater than 20

45
Q

enzymes — activation energy

A

lower

46
Q

which has a higher melting point E or Z?

A

Z

47
Q

— are in trans fat (they are more easily stacked)

A

Z

48
Q

the side of the reaction with the — enthalpy will be the most stable

A

highest

49
Q

the — curve is the rate limiting one

A

highest

50
Q

reactive intermediate

A

carbocation

51
Q

why are some carbocations more stable than others?

A

hyperconjugation

52
Q

hyperconjugation — bonds

A

stabilizes

53
Q

hyperconjugation is when —

A

alkyl groups contribute a negative charge (just share, don’t actually donate)

54
Q

regioselective

A

reaction goes to a certain region, will form the most stable isomer

55
Q

lowers activation energy

A

catalyst

56
Q

a catalyst usually introduces a —

A

intermediate

57
Q

the more acidic molecule has the — stable base

A

most

58
Q

delocalizes a negative charge

A

resonance

59
Q

equilibrium will favor whichever side has the —

A

more stable negative charge ( conj base)

60
Q

different positions that a molecule can twist

A

conformations

61
Q

a matter of R or S

A

configuration

62
Q

cis/trans isomers are

A

diastereomers

63
Q

compounds that have stereocenters but also has symmetry making it the mirror image of itself

A

a meso compound

64
Q

a compound is chiral if it is : (2)

A

they have stereocenters and are not meso compounds

65
Q

chiral compounds rotate polarized light, if the rotation is clockwise then we say it is —, if it is counterclockwise, we say it is —

A

+

-

66
Q

when will no light be rotated?

A

if we have a 50/50 mixture of enantiomers (racemic)—because the rotations cancel each other out

67
Q

S/R and +/- are or are not related?

A

are not

68
Q

whether or not a compound is + or - often depends on

A

temperature

Organic Chemistry (3 decks)

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