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final Flashcards

1
Q

reactants for the halogenation of alkenes

A

Br2

DCM (CH2Cl2) (basically, a non-nucleophilic solvent. if you used something like water, you would produce a halohydrin)

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2
Q

for the halogenation of alkenes, is it stereospecific?

A

yes

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3
Q

for the halogenation of alkenes, is it regiospecific?

A

no

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4
Q

for the halogenation of alkenes, is it anti or syn?

A

anti

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5
Q

what is the intermediate for the halogenation of alkenes, is it stereospecific?

A

halonium ion

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6
Q

regioselectivity

A

preference for the placement of a bond in one location over another (major vs. minor product with differences in bond positions)

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7
Q

stereospecificity

A

preference for stereochemistry over another (major vs. minor product with differences in stereochemistry)

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8
Q

for the halogenation of alkenes, is it concerted?

A

yes, the first step is

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9
Q

for the halogenation of alkenes, does a racemic mixture occur?

A

yes, a racemic mixture of enantiomers occur

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10
Q

explain cis vs. trans for the halogenation of alkenes

A

trans results in bromine both being wedges or both being dashes, due to rotation of sigma bond.

cis results in one bromine being a wedge and the other being a dash.

THIS MAKES MESO ISOMERS

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11
Q

reactants for the hydrogenation of alkenes

A

H2 gas

Pd/C (paladium on carbon) –> can be any metal catalist: ex. Pt, Ni, etc.

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12
Q

for the hydrogenation of alkenes, is it stereospecific?

A

yes

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13
Q

for the hydrogenation of alkenes, is it regioselective?

A

no

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14
Q

for the hydrogenation of alkenes, is it anti or syn?

A

SYN (both hydrogens added from the same side)

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15
Q

what’s the intermediate for the hydrogenation of alkenes?

A

alkene-metal complex

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16
Q

for the hydrogenation of alkenes, is it concerted?

A

yes, full rxn is

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17
Q

for the hydrogenation of alkenes, does a racemic mixture occur?

A

yes, a racemic mixture of enantiomers occur

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18
Q

what are the reactants for epoxidation

A

MCBA –> consists of a benzene ring, peroxy group (-OOH) and a carboxylic acid group (-COOH)

ROR –> ethereal solvent (R-O-R where R = an alkyl group (series of carbons and hydrogens like methyl, ethyl, etc.))

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19
Q

for the epoxidation of alkenes, is it a racemic mixture?

A

yes, racemic mixture: if it has n chiral centers, it can have 2^n stereoisomers

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20
Q

for the epoxidation of alkenes, is it regioselective?

A

yes

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21
Q

for the epoxidation of alkenes, is it SYN or ANTI?

A

SYN

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22
Q

for the epoxidation of alkenes, what is the intermediate?

A

transition state occurs not a defined intermediate

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23
Q

for the epoxidation of alkenes, is it stereospecific?

A

yes

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24
Q

for the epoxidation of alkenes, is it concerted?

A

yes

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25
Q

what are the reagants for ozonolysis

A

1.) O3

2.) [H] –> a reducing agent (ex. Zn, Me2S, or PPh3)

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26
Q

for ozonolysis of alkenes, is there a racemic mixture produced?

A

no

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27
Q

for ozonlysis of alkenes, is it regioselective?

A

yes

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28
Q

for ozonlysis of alkenes, is it SYN or ANTI?

A

SYN

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29
Q

for ozonlysis of alkenes, what is the intermediate?

A

criegee intermediate (a carbonyl oxide with two charge centers)

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30
Q

for ozonlysis of alkenes, is it stereospecific?

A

no

31
Q

for ozonlysis of alkenes, is it concerted?

A

yes

32
Q

for halohydrin formation, what should be considered?

A

that H2O (the oxygen) attaches to the more substituted carbon

33
Q

what are the reagents in a halohydrin formation of alkenes?

A

Br2 / Cl2

H2O

34
Q

for a halohydrin formation of alkenes, what is the intermediate?

A

cyclic chloronium ion
(has partial carbocation behavior which is why water attaches to it)

35
Q

stereospecificity vs. stereoselectivity

A

stereospecificity –> we only have one product

stereoselectivity –> we could have multiple products

36
Q

for a halohydrin formation of alkenes, does it produce a racemic mixture?

A

if an ANTI addition, then yes

37
Q

for a halohydrin formation of alkenes, is it regioselective?

A

yes

38
Q

for a halohydrin formation of alkenes, is it ANTI or SYN?

A

ANTI

39
Q

for a halohydrin formation of alkenes, is it stereoselective?

A

yes

40
Q

for a halohydrin formation of alkenes, is it concerted?

A

no

41
Q

what are the reagents for the hydroboration of alkenes?

A

1.) BH3, THF

2.) H3SO4, OH

42
Q

for a hydroboration of alkenes, does a racemic mixture occur?

A

a racemic mixture can from because you can add from either the top or bottom faces

43
Q

for a hydroboration of alkenes, is it regioselective?

A

yes

44
Q

for a hydroboration of alkenes, is it SYN or ANTI?

A

SYN

45
Q

for a hydroboration of alkenes, what is the intermediate?

A

boron intermediate

46
Q

for a hydroboration of alkenes, is it concerted?

A

yes

47
Q

what are the reagants for an acid catalyzed hydration with alcohol?

A

strong acid (ex. H2SO4) and an alcohol (ex. CH3OH)

48
Q

for an acid catalyzed hydration with alcohol, does a racemic mixture occur?

A

no

49
Q

for an acid catalyzed hydration with alcohol, is it regioselective?

A

yes

50
Q

for an acid catalyzed hydration with alcohol, is it anti or syn?

A

usually anti, but depends

51
Q

for an acid catalyzed hydration with alcohol, what is the intermediate?

A

a carbocation

52
Q

for an acid catalyzed hydration with alcohol, is it stereoselctive?

A

no

53
Q

for an acid catalyzed hydration with alcohol, is it concerted?

A

no

54
Q

what are the reagants for a hydration reaction

A

HA

H2O

55
Q

for a hydration reaction, is it regioselective?

A

yes

56
Q

for a hydration reaction, is it SYN or ANTI?

A

either can occur

57
Q

for a hydration reaction, what is the intermediate?

A

full carbocation

58
Q

for a hydration reaction, is it stereoselective?

A

no

59
Q

for a hydration reaction, is it concerted?

A

yes

60
Q

hydration reaction vs. hydroboration

A

hydration –> oxygen on more substitutes carbon

hydroboration –> oxygen on less substituted carbon

this has to do with the intermediate and its stability. Ex. boron in hydroboration just prefers it this way. Also, steric hinderance. if there is a methyl group attached to one carbon on the double bond and there is a hydrogen on the other carbon attached to the double bond, the boron prefers the one attached to just the hydrogen because the methyl group is so big.

61
Q

what are the reagants for the simmons-smith cyclopropanation reaction?

A

CH2I2

Zn(Cu)

62
Q

for a simmons-smith cyclopropanation reaction, does it it produce a racemic mixture?

A

no

63
Q

for a simmons-smith cyclopropanation reaction, is it regioselective?

A

no

64
Q

for a simmons-smith cyclopropanation reaction, is it SYN or ANTI?

A

SYN

65
Q

for a simmons-smith cyclopropanation reaction, what is the intermediate?

A

methylene free radical

66
Q

for a simmons-smith cyclopropanation reaction, is it stereospecific?

A

yes

67
Q

for a simmons-smith cyclopropanation reaction, is it concerted?

A

yes

68
Q

what are the reagants for a mineral acid addition?

A

1.) HBr (neat)

69
Q

for a mineral acid addition reaction, does it produce a racemic mixture?

A

no

70
Q

for a mineral acid addition reaction, is it regioselective?

A

yes

71
Q

for a mineral acid addition reaction, is it SYN or ANTI?

A

ANTI

72
Q

for a mineral acid addition reaction, what is the intermediate?

A

a full carbocation

73
Q

for a mineral acid addition reaction, is it stereospecific?

A

no

74
Q

for a mineral acid addition reaction, is it concerted?

A

no

ochem (2 decks)

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