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Organic Chemistry > Ch 7 & 8 Substitution & Elimination reactions > Flashcards

Ch 7 & 8 Substitution & Elimination reactions Flashcards

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1
Q

Sn1 kinetics

A

1st order

K[R-X]

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2
Q

Sn2 mechanism

A

1-step, concerted reaction

no intermediate

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3
Q

Sn1 mechanism

A

2-step

1 intermediate = carbocation

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4
Q

Sn2 stereochemistry

A

configuration inversion, stereospecific

always backside attack

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5
Q

Sn1 stereochem

A

retention + inversion

non-stereospecific, racemic mixture (because does backside and frontside attacks)

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6
Q

Sn2 R-group preference/identity

A

methyl>primary>2ndary>tertiary

because of steric effect
AKA fewer R groups if better

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7
Q

Sn1 R group preference/identity

A

tertiary>2ndary>primary>methyl

because of electron effect
AKA more substituted (more R groups) is better bc is more stable carbocation

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8
Q

Sn2 alykl halide

A

(most favored to not possible) H3C > RH2C >R2HCX >R3C

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9
Q

Sn1 Alkyl Halide

A

(most favored to not possible)

R3C-X > R2HC-X > RH2C-X > H3

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10
Q

Sn2 nucleophile

A

good nucleophile preferred (- charge, like OH-)

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11
Q

Sn1 nucleophile

A

does not matter

usually uses weak Nucleophile (like HOH) to avoid competition with Sn2

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12
Q

Sn2 leaving group preference

A

good leaving group

bc have to leave in rate-limiting step

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13
Q

Sn1 leaving group

A

good leaving group

bc has to leave in rate-limiting step

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14
Q

ex of order of pref of good leaving group

A

I > Br > Cl > F

increasing pref of halogens going down PT

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15
Q

Sn2 solvent

A

polar, aprotic

ex: acetone

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16
Q

Sn1 solvent

A

polar, aprotic

ex CH3CH3CH2-OH

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17
Q

E2 Kinetics

A

2nd order

rate = K[R-X][Base]

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18
Q

E1 Kinetics

A

1st order

rate = K[R-X]

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19
Q

E2 mechanism

A

1-step, concerted

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20
Q

E1 mechanism

A

2 steps

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21
Q

E2 intermediate?

A

no intermediate

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22
Q

E1 intermediate?

A

carbocation

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23
Q

E2 alkyl halide

A

(most favored to possible)
R3C-X > R2HC-X > RH2C-X
bc of steric effect, favors more substituted R groups, more stable

24
Q

E1 alkyl Halide

A

(most favored to NOT possible)
R3C-X > R2HC-X > RH2C-X
bc of steric effect, favors more substituted R groups, more stable

25
Q

E2 base

A

favors good base

26
Q

E1 base

A

does not matter

but tries to use weak base to avoid competition with E2

27
Q

does follow E2 Zaitsev rule?

A

yes

28
Q

does E1 follow Zaitsev rule?

A

yes

29
Q

E2 stereochem

A

favors antiperiplanar = transition state

H and X on opposite sides

30
Q

E1 stereochem

A

no stereochem (carbocation is flat)

31
Q

what is the Zaitsev rule

A

the major product is labeled as the more stable (more substitued double bonded) elimination product
the minor product is less stable/less substituted

32
Q

mechanism for RCH2X (primary) with a strong base and Nu?

A

Sn2 and E2

33
Q

mechanism with RCH2X (primary) with strong bulky base?

A

favors E2

34
Q

Mechanism for RCH2X (primary) with a strong Nu?

A

favors Sn2

35
Q

mechanism for (R3C-X) (tertiary) with a strong base?

A

E2 (NEVER SN2)

36
Q

Mechanism for tertiary (R3C-X) with weak base and Nu?

A

Sn1 and E1

37
Q

mechanism for 2ndary (R2CH-X) with strong base and Nu?

A

Sn2 and E2

38
Q

mechanism for 2ndary (R2CH-X) with strong and bulky base

A

E2

39
Q

mechanism for 2ndary (R2CH-X) with a weak base and Nu?

A

Sn1 and E1

40
Q

if the alkyl halide is primary, what is NOT possible and why?

A

SN1 and E1 because of carbocation stability

41
Q

if the alkyl halide is tertiary, what is not possibly and why?

A

Sn2 bc of steric hinderance

42
Q

if the electron pair donor is bulky, is it a Nu or a Base?

A

base

43
Q

if OH- a base, Nu, or both?

A

both

44
Q

is OCH3 a base, Nu, or both?

A

both

45
Q

is H- a base, Nu, or both?

A

base, bc too small to be a Nu

46
Q

is H2N a base, Nu, or both?

A

both

47
Q

is I- a base or Nu?

A

Nu

48
Q

if a electron donor has a neg charge, is it strong or weak?

A

STRONG

49
Q

what classifies a reaction as a heterolysis

A

one-step, no intermediate = concerted rx

50
Q

what classifies a reaction as a homolysis?

A

is a stepwise reaction = has a reactive intermediate

51
Q

what is activation Energy?

A

energy difference between transition state and reactant

energy barrier that must be overcome for a rx to occur

52
Q

what classifies the transition state

A

the species with the max value of energy

53
Q

what is the rate-limiting step

A

step with the highest activation energy

the slow step

54
Q

what is a catalyst

A

accelerates a reaction by lowering the activation energy, while itself is unchanged during the rx

55
Q

Sn2 Kinetics

A

2nd order

K[R-X][Nu]

Organic Chemistry (1 decks)

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