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chemistry > alkene mechanisms > Flashcards

alkene mechanisms Flashcards

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1
Q

markovinkov’s rule

A

the H+ ion will go to the less substituted carbon (making the more stable carbocation)

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2
Q

anti-markovinkov’s rule

A

the H+ ion will go to the more substituted carbon
- only works with HBr in presence of peroxide (ROOR)

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3
Q

what rule do HCl and HI follow?

A

Markovinkov’s Rule

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4
Q

What does HBr need to follow anti-markovinkov’s rule?

A

peroxide (ROOR)

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5
Q

Addition of Water

A
  • adding H2O
  • forms an alcohol
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6
Q

what rule does addition of water follow?

A

Markovinikov’s Rule

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7
Q

common reagents of addition of water

A

H2SO4/H20
H3PO4/H20
H3O+

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8
Q

Hydration by Oxymercuration-Demurcuration

A

no carbocation and no rearrangements formed

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9
Q

what rule does hydration by oxymercuration-demercuration follow?

A

Markovinikov’s Rule

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10
Q

common reagents of hydration by oxymercuration-demurcuration

A

Hg(OAc)2,H2O/NaBH4

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11
Q

Alkomercuration-Demercuration

A

no carbocation and no rearrangements

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12
Q

what rule does alkomercuration-demercuration follow?

A

Markovinkov’s Rule

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13
Q

common reagents of alkomercuration-demercuration

A

Hg(OAc)2, OH-/NaBH4

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14
Q

hydroboration

A

addition of borane

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15
Q

what rule does hydroboration follow?

A

anti-markovinikov

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16
Q

common reagents of hydroboration

A

BH3

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17
Q

hydroboration-oxidation

A

syn addition

18
Q

common reagents of hydroboration-oxidation

A

BH3THF/H2O2, OH-
BH3THF/H2O2 NaOH-

19
Q

addition of halogens to alkenes

A

addition of Cl2,Br2,I2
no rearrangements
on adjacent carbons

20
Q

what addition is addition of halogens?

A

anti (trans)
- have to show stereochemistry and its enantimer

21
Q

halohydrin

A

alcohol with halogen on adjacent carbon
must have good nucleophile (H2O)

22
Q

what rule does halohydrin follow?

A

Markovinkov’s Rule

23
Q

what addition does halohydrin follow?

A

anti product (trans)

24
Q

what addition is catalytic hydrogenation?

A

syn addition (same side)

25
Q

common catalysts for catalytic hydrogenation

A

Pt, Pd, Ni, Wilkinson’s Catalyst
example: H2/Pt, H2/Pd

26
Q

addition of carbenes

A

adding CH2 to double bond which creates cyclopropane

27
Q

3 methods of adding carbenes

A

diazomethane, simmons-smith, and alpha elimation of haloform

28
Q

diazomethane

A

N2 + CH2

29
Q

simmons-smith reagent

A

CH2I2 + ZN —> ICH2ZNI

30
Q

alpha elimination reagents

A

CHCl3/KOH,H2O
haloform reacts with base

31
Q

epoxidation

A

alkene reacts with peroxyacid(OOH) to form epoxide (3 membered ring with 2 carbons and O)

32
Q

epoxidation reagent

A

perobenzoic acid (R-C(double bond O)-O-O-H)

33
Q

opening of epoxide ring

A

acid catalyzed
- attacked by acid
- then water attacks protanated epoxide and a transdiol is formed (one on dash, other on wedge)

34
Q

syn-hydroxylation

A

addition of two hydroxyl groups (one at each carbon of double bond)

35
Q

syn-hydroxylation reagents

A

OsO4/H2O2
KMnO4/OH ( permaganate has to be cold to form diols and hydrolysis with base)

36
Q

oxidative cleavage

A

pi and sigma bonds break
C=C become C=O

37
Q

two methods of oxidative cleavage

A
  1. warm/concentrated KMnO4
  2. ozonolysis
38
Q

cleavage with MnO4

A

the disubstituted C forms Ketone
the monosubstituted C forms carboxylic acid
terminal = CH2 forms CO2

39
Q

ozonolysis

A

forms ketone and aldehydes

40
Q

oxynolysis reagents

A

O3/(Ch3)S

41
Q

syn addition

A

cis (same side)

42
Q

anti addition

A

trans (opposite sides)
show stereochemistry and enantimer

chemistry (2 decks)

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