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Organic Chem > Test 4 > Flashcards

Test 4 Flashcards

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1
Q

S* -> R*
reactant is 100% S
product is 100% R

A

considered an inversion

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2
Q

S* -> S*
reactant is 100% S
product is 100% S

A

considered retention of configuration

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3
Q

S* -> (S* + R*)
reactant is 100% S
product is 50/50%

A

considered racemization

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4
Q

substitute out the ___________

A

leaving group

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5
Q

substitute in the ___________

A

nucleophile

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6
Q

if the leaving group is to the left, the attack will come from the ______

A

right

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7
Q

what is the utility of an SN2 reaction

A

allows for a wide range of heteroatoms

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8
Q

what type of alkyl halide cannot do SN2 reactions

A

3rd degree

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9
Q

two reasons for opposite side attack

A
  1. columbic (charged) repulsions between nucleophile lone pair and the lone pair on the halogen
  2. steric bulk size of the halogen
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10
Q

best type of solvent for Sn2 reactions

A

polar aprotic

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11
Q

nonpolar solvents

A

no heteroatoms
just CH atoms

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12
Q

polar aprotic solvents

A

has heteroatoms like O, N, S (polar)
lack of O-H and N-H bonds (aprotic)

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13
Q

polar protic

A

has N-H or O-H bonds

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14
Q

why are polar protic solvents NOT good for Sn2 reactions

A

will have unwanted BL acid base reactions

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15
Q

why are nonpolar sovlents NOT good for Sn2 reactions

A

granular salt will not dissolve

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16
Q

racemization definition

A

optically active compounds (only one enantiomer) are converted into an equal mixture of enantiomers with zero optical activity

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17
Q

enantiomer

A

nonsuperimposable mirror images

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18
Q

diasteromers

A

nonsuperimposable, non mirror images

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19
Q

1st degree alkyl halide

A

ONE other carbon attached to the carbon attached to the halogen

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20
Q

2nd degree alkyl halide

A

TWO other carbon attached to the carbon attached to the halogen

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21
Q

3rd degree alkyl halide

A

THREE other carbon attached to the carbon attached to the halogen

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22
Q

X

A

halogen

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23
Q

geminal

A

coming off of the same carbon

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24
Q

vicinal

A

coming off of adjacent carbons

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25
hydrogen bonds
hydrogen bound to oxygen, nitrogen, or flourine
26
higher dielectric constant =
more polar
27
dipole moment vectors show
magnitude and direction of polarity
28
steps for SN2 reactions
separate attacker (-) from (K, Li, Na) draw opposite side attack leaving group leaves, attacking group attaches on opposite side stereochemical inversion
29
substrates in SN2 reactions are
sp3 hybridized
30
good leaving groups
weak bases ex. halides
31
poor leaving groups
strong bases
32
what degree of carbons can preform SN2 reactions
1 and 2 ONLY 3rd degree CANNOT
33
impact of double bonds on SN2 reactions
leaving group directly attached to a double bond = NO REACTION
34
nucleophilcity increases with
size
35
polar protic vs polar aprotic
polar protic: proton (H) bound to an electronegative atom polar aprotic: NO H bonds
36
nucleophile charge
negative
37
SN2 stands for
substitution nucleophilic attack 2 reactants (rate determining step)
38
best degree alkyl halide for SN2 reactions
first degree
39
order of reactivity for SN2 reactions
methyl > 1st degree > 2nd degree > 3rd degree
40
aromatic compounds and SN2 reactions
DO NOT participate because of double bonds carbon with halide attached must be at least one carbon removed from the ring for SN2 to occur
41
how to determine best compound for SN2 reaction if all are same degree carbons
look at adjacent carbons (1st, 2nd, 3rd, 4th degree?)
42
if substrates are the same, how do you determine which reaction will occur faster?
look at nucleophiles stronger nucleophile (-) = raster reaction
43
periodic trends in regards to nucleophiles
moving from right to left, basicity increases and therefore nucleophile strength increases moving top to bottom, atom size and electronegativity increases, therefore nucleophile strength increases due to increased polarity of atom
44
can SN2 reaction occur on sp2 molecules
no
45
rate equation for SN2
rate = k [Rx] [Nu]
46
invert
in all cases of a halogen
47
if less than 0.5 D
NON-polar
48
nucleophilic attackers
negative atoms
49
alkyl halide
RX
50
leaving group
X (F, Cl, Br, I)
51
if leaving group is on a w/h
nucleophile will end up on the inverted w/h
52
push only happen with
in plane
53
determining which RX will have faster SN2 reaction
degree of alkyl halide degree of electronegativity of leaving group
53
as electronegativity increases
basicity decreases
54
as steric bulk increases
basicity increases
55
1 carbon
common: meth IUPAC: form
56
2 carbon
common: eth IUPAC: acet
57
3 carbon
common: prop IUPAC: propion
58
4 carbon
common: but IUPAC: butyr
59
5 carbon
common: pent IUPAC: valer
60
6 carbon
common: hex IUPAC: capro
61
allyl
3 carbons x- - =
62
vinyl
2 carbons X - =
63
benzyl
7 carbons 6 carbon ring - -x
64
phenyl
6 carbons 6 carbon ring - x
65
amide
NH2
66
cyanide
-CN
67
acetylide
-C tripple bond C-
68
greater orbital size mismatch =
weaker bond
69
weaker bond =
faster leaving group
70
non resonance nucleophiles
negative charge only on 1 atom faster than resonance nucelophiles
71
free radicles
one unpaired electron
72
stability for carbocations
3 > 2 > 1 > methyl
73
stability for carboanions
methyl > 1 > 2 > 3
74
stability for radicals
3 > 2 > 1 > methyl
75
strong nucleophiles are structurally
NOT BULKY
76
why are polar aprotic solvents best for SN2 reactions
no unwanted BL acid base reactions both organic and ionic nucleophiles will dissolve

Organic Chem (6 decks)

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