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Organic Chemistry > Chapter 8 > Flashcards

Chapter 8 Flashcards

1
Q

addition reactions are when with one _______ bond is broken and 2 new _________ bonds are formed

A

pi, sigma

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2
Q

addition reactions are the inverse of what type of reaction?

A

elimination

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3
Q

Markovnikov’s Rule

A

predicts that the carbocation will always form on the most stable carbon

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4
Q

hydrohalogenation

A
  • H-X
  • creates a carbocation intermediate
  • produces an alkyl halide
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5
Q

maokovnikov or anti-maokovnikov: hydrohalogenation

A

markovinivok

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6
Q

what type of intermediate does an HBr and ROOR (hydrohalogenation) reaction have?

A

radical

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7
Q

maokovnikov or anti-maokovnikov: HBr/ROOR (hydrohalogenation)

A

anti-markovnikov

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8
Q

acid-catalyzed hydration

A
  • H2O/H2SO4
  • intermediate = carbocation
  • product = alcohol
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9
Q

maokovnikov or anti-maokovnikov: acid-catalyzed hydration

A

mark

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10
Q

oxymercuration-reduction

A
  • Hg(OAC)2, H2O / NaBH4, NaOH
  • intermediate = bridged ion
  • product = alcohol
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11
Q

maokovnikov or anti-maokovnikov: oxymercuration-reduction

A

mark

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12
Q

hydroboration-oxidation

A
  • BH3 (or other B) / H2O2, NaOH
  • stereochemistry = syn addition
  • product = alcohol
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13
Q

syn addition

A

cis products

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14
Q

maokovnikov or anti-maokovnikov: hydrobromination-oxidation

A

anti-mark
(OH in least stable position)

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15
Q

hydrogenation

A
  • H2 / Ni, Pt, (or some type of metal catalyst)
  • stereochemistry = syn addition
  • product = alkenes
    HYDROGEN IS JUST ADDED TO MAKE THE CARBONS HAPPY AND HAVE NO DOUBLE BONDS OR IONS
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16
Q

maokovnikov or anti-maokovnikov: hydrogenation

A

N/A (adding the same thing - hydrogens)

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17
Q

halogenation

A
  • X2
  • intermediate = bridged ion
  • stereochemistry = anti
  • product = vicinal dihalides
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18
Q

vicinal

A

next to each other in the molecule (1,2)

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19
Q

maokovnikov or anti-maokovnikov: halogenation

A

N/A (adding the same thing - halides)

20
Q

halohydrin

A
  • X2 / H2O
  • intermediate = bridged ion
  • stereochemistry = anti
  • product = halohydrin
21
Q

maokovnikov or anti-maokovnikov: halohydrin

A

mark

22
Q

cyclopropanation uses what intermediates?

A

cabene or carbenoid

23
Q

Carbenes are reactive intermediates. They are unstable because they violate the _________________

A

octet rule

24
Q

4 methods commonly used to introduce carbene intermediates

A
  • CH2
  • CHCl3 / tert-butoxide
  • N=N-CH2 / hv
  • CH2I2 / Zn(Cu)
25
Q

epoxides are added to double bonds using ______________

A

peroxy acid

26
Q

common reagents for epoxidation are _________ and _________

A

mCAPBA and MMPP(RCO3H)

27
Q

acid catalyzed ring opening: following protonation of the epoxide the nucleophile will attack the side of the ring with the most _____________ character

A

positive

28
Q

base catalyzed ring opening: the strong nucleophile will attack the side of the ring that is _____________ substituted

A

least

29
Q

dihydroxylation

A

adds 2 OH to one double bond (vicinal and syn)

30
Q

ozonolysis

A
  • O3
  • cut the double bond and add an O
31
Q

reductive workup

A
  • S(CH3)2 or Zn/HOAc
  • aldehyde and ketones
32
Q

oxidative workup

A
  • H2O2
  • carboxylic acids and ketones
33
Q

oxidative cleavage

A
  • KMnO3 / heat
  • cut the double bond and add an O and OH
34
Q

alkyne halogenation

A

product = tetrahalides
(vicinal halides –> total of 4 halides)

35
Q

free radical polymerization

A

alkenes in excess to extend the propagation step almost indefinitely

36
Q

What is often used when KI, H3PO4 is written?

A

H-I

37
Q

Anytime we have a carbocation intermediate you need to look for a _________ or __________ shift

A

hydride or methyl

38
Q

_________ cannot have a shift occur

A

Hg(OAc)

39
Q

what mechanism as initiation, propogation and termination steps because they have radicals?

A

hydrobromonation-oxidation

40
Q

hydrogenation definition

A

reduction = gains electron density for carbon

41
Q

markovnikov rule

A

H tends to go to the least subsidized side and the + goes to the more substituted side

42
Q

are epoxides reactive?

A

VERY reactive (due to angle strain)

43
Q

acidic - ring opening epoxide

A

more substituted position attacked by a nucleophile (SN1)

44
Q

basic - ring opening epoxide

A

less substituted position attacked by a nucleophile (SN2)

45
Q

carbenes

A

neutral molecule containing divalent carbon with only 6 electrons in its valence shell

46
Q

which reactions have a syn addition as part of the mechanism?

A
  • BH3, THF / H2O2, NaOH
  • H2, Pd
47
Q

anti-markovnikov reactions

A

BH3 and HBr + ROOR

Organic Chemistry (9 decks)

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