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elimination Flashcards

1
Q

elim vs sn

A

-both have leaving groups but sn replaces it w nu
-often compete
-emilination= FORM ALKENE

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2
Q

formation of alkene

A

caused by the loss of the beta hydrogen

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3
Q

two main mechanism

A

e1 and e2

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4
Q

e2

A

bimolecular
-involves the substrate and the base in one single step

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5
Q

where will the double bond form?

A

-all about regiochemistry
-how many groups on each double bond

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6
Q

zatziev product

A

-more substituted alkene
-most times is the major product UNLESS IT IS A BBB
-ALL ABOUT WHERE THE RXN TAKES PLACE

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7
Q

BBB

A

chose hofman product/ less sub
-tbuok and lda

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8
Q

product of e2 reaction

A

-can be controlled based on which base you use cause one leads to more sub and one leads to less sub product

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9
Q

identical beta h positions

A

-regiochemistry is not an issue, no matter where rxn happens same outcome
-stereochem important
-if cis and trans are product, trans is favored

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10
Q

steroselective e2

A

-cis and trans are the product and they both have the same regiochemistry
-trans is favored
-results in a mixture

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11
Q

stereospecific e2

A

-antiperiplanar
-results in one alkene
-draw newman projection to make sure they are in a line
-does not produce stereoisomers

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12
Q

one proton

A

-is stereospecific, will only get one alkene
-draw newman projection and make sure it is aniperiplanar

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13
Q

newman projection

A

-use to determine the stereoisomer product of e2 reaction

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14
Q

e1

A

two steps
-leaving group leaves
-lose of the proton
-the base is not involved in step one therefore unimolecular all about the substrate
-compete with sn1 and product is a mixture

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15
Q

e1 alkyl halids

A

prefer secondary and tertiary
-primary will not go e1

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16
Q

sn2

A

will not be tertiary (too bulky)
-but e2 can be tertiarty bc there is not attack

17
Q

e2 alkyl halide

A

tertiary is fastest

18
Q

oh

A

bad leaving group

19
Q

e1 of an alcohol

A

there will be a protonation step first because oh is a bad leaving group
-strong acid used to protonate
-product is h2o+ which is an excellent leaving group

20
Q

e1 and e2

A

prefer zatsev product as the major product

21
Q

e1 product

A

CAN NOT BE CONTROLLED BY USING A BBB

22
Q

regiochemical outcome

A

where the alkene bond will go which will lead to zaitzev or hoffman

23
Q

are e1 reactions stereospecific

A

NO
-do not need antiperiplanarity to run reaction
-they are stereoselective when cis and trans happen

24
Q

stereospecific

A

changing reactant changes product
-only e2

25
Q

stereoselective

A

-choice btween 2 paths that lead to 2 products (cis and trans)

26
Q

three steps to determine products

A

-function of the reagent
-analyze substrate and expected mechanisms
-regiochemical and stereochemical requirements

27
Q

reagent

A

-is it functioning as a nu or as a base

28
Q

when are nucleophilicity and basicity parallel?

A

when they are in the same row of the periodic table
-same row, more electroneg= weaker base

29
Q

hn- vs ho-

A

ho- is the weaker base because the oxygen is more elctronegative and stabalizes charge better than nitrogen

30
Q

same column

A

-basicity and nu are not parallel
-OH- vs SH-, OH- is the stronger base because it is smaller and sh is the stronger nu bc it can polarize charge bc of its size

31
Q

halides especially iodine

A

function mostly as nu= substitution

32
Q

strong nu

A

highly polarizable (big)

33
Q

strong base

A

e2

34
Q

so4

A

e1

35
Q

vicinal dihalide

A

halides on adjacent carbons
-goes to most acidic protons (the ones that have the halides because they have partial positives)

36
Q

double hydrohalogenation

A

e2 reaction twice that synthesizes an alkyne
-use the base twice

37
Q

nh2

A

strong base

38
Q

geminal dihalide

A

halogens are on the same carbon (gemini twins same mother carbon)
-must be alpha to terminus (next to terminus)
-need excess base
-go for terminal protons

39
Q

dehydrohalogenation e2 reactions

A

-double hydrohalogenations to geminal dihalides or vicinal dihalides

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