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CHEM 2420- organic chem 2 > Midterm 1 review > Flashcards

Midterm 1 review Flashcards

1
Q

what type of substituents do each the diene and dienophile have to create a higher yield

A

diene: electron donating subs
dienophile: electron withdrawing subs

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2
Q

what is the product of the dienophile having outwards groups

A

wedges

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3
Q

what is the product of the dienophile having inwards groups

A

dashes

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4
Q

what is the product of the diene having outwards groups

A

dashes

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5
Q

what is the product of the diene having inwards groups

A

wedges

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6
Q

which product of diels-alder is more common

A

ENDO

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7
Q

which isomer of the diene causes the reaction to go faster: cis or trans

A

cis, because trans subs interfere with the pi electrons approach

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8
Q

how do you make an acid from an alcohol

A

oxidization of a 1 alc

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9
Q

how do you make a ketone from an alcohol

A

oxidization of a 2 alc

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10
Q

how do you make an aldehyde from an alc

A

PCC with 1 alc

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11
Q

how do you make a carbonyl from an alkene

A

ozonolysis (O3, DCM and then DMS)

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12
Q

how do you make a carbonyl from an alkyne

A

hydration (H3O+ and Hg2+)

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13
Q

how do you make a carbonyl from an ester

A

reduction (DIBAL and H+)

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14
Q

how do you make a carbonyl from a nitrile

A

reduction (DIBAL and H+)

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15
Q

how do you make a carbonyl from an acyl halide

A

reduction (LAH then H+)

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16
Q

product of H type?

A

alcohol (1o or 2o depending on the starting carbonyl)

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17
Q

product of O type?

A

ketals or acetals

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18
Q

steps of adding and removing protecting groups?

A

add via H+ and the group, then do your reaction, then acid wash to remove the group

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19
Q

product of hydration of carbonyls?

A

geminal diol (two alcs)

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20
Q

in regards to electron deficiency, how do you get a faster reaction rate

A

a more electron deficient carbonyl = faster rate

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21
Q

what will make a carbonyl more electron deficient?

A

electron withdrawing subs

ie C(Cl)3

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22
Q

product of S type?

A

thioacetal to ketone or hydrocarbon

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23
Q

product of N type?

A

imine or enamine

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24
Q

how do you reduce a carbonyl to an alkane

A

clemmensen or wolff-kishner

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25
Q

product of C type?

A

cyanohydrin

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26
Q

product of grignard?

A

alcohol and a new CC bond

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27
Q

product of wittig?

A

new C=C bond

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28
Q

product of cannizzaro?

A

acid and alcohol (50/50)

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29
Q

product of baeyer villager?

A

ester (or carb acid if one R group is an H)

30
Q

with carbonyls: how to make an alcohol

A 
H type (LAH then water, or NaBH4 and water)
OR
grignard
OR 
cannizzaro (will also make acid)
31
Q

with carbonyls: how to make a ketal or acetal

A

O type (H+ and ROH)

32
Q

with carbonyls: how to make a geminal diol

A

hydrate a carbonyl (acidic or basic)

33
Q

with carbonyls: how to make a ketone

A

S type with hydrolysis

34
Q

with carbonyls: how to make a hydrocarbon

A 
S type with desulfurization
OR
clemmensen
OR 
Wolff-kishner
35
Q

with carbonyls: how to make an imine

A

N type with 1o amine

36
Q

with carbonyls: how to make an enamine

A

N type with 2o amine

37
Q

with carbonyls: how to make a cyanohydrin

38
Q

with carbonyls: how to make a new C=C bond

39
Q

with carbonyls: how to make a carb acid

A

cannizzaro (will also make alcohol)
OR
baeyer villager (if R=H)(two possible products)

40
Q

with carbonyls: how to make an ester

A

baeyer villager (this could be an acid if R=H)

41
Q

with carbonyls, how do you make a new C-C bond

A

S type, Grignard

42
Q

with carbonyls, how do you get a new C=C bond

43
Q

in regards to electron withdrawing substituents, how do you increase acidity of acids

A

more electron withdrawing subs increases acidity

44
Q

how do you make a carb acid from alcohols

A

oxidation of 1o alc

45
Q

how do you make a carb acid from an aldehyde

A

oxidation of a 2o alc

HNO3 or Tollens

46
Q

how do you make a carb acid from an alkyne

47
Q

how do you make a carb acid from a nitrile

A

hydrolysis (acidic or basic)

48
Q

how do you make a carb acid from an acyl halide

A

grignard with carbon dioxide

49
Q

from a carb acid: how do we make an alcohol

A

reduction (LAH then water)

50
Q

from a carb acid: how do we make an aldehyde

A

reduction to an alcohol, then PCC

51
Q

from a carb acid: how do we make a carboxylic acid derivative

A

react with LG then Nuc

52
Q

how do we make an acyl halide

A

carb acid reacts SOCl2 (LG), then nuc (HCl)

53
Q

from an acyl halide: how do we product a tertiary alc

A

C type (grignard)

54
Q

from an acyl halide: how do we product a primary alc

A

H type (LAH)

55
Q

from an acyl halide: how do we product an aldehyde

A

LTTBA then H+

56
Q

from an acyl halide: how do we product a ketone

A

lithium dialkyl cuprates

57
Q

from an acyl halide: how do we product an amine

58
Q

from an acyl halide: how do we product an ester

59
Q

how do we make anhydrides

A

acyl halide + carb acid

60
Q

from anhydrides: how do we make carb acids and carbonyls

A

react with any nuc

61
Q

what is the name for ester formation

A

transesterification

62
Q

how do you make esters from carb acids

A

ROH and H+

63
Q

how do you convert esters back into carb acids

A

hydrolysis

64
Q

from esters: how do you make a primary alc

A

LAH then H3O+

65
Q

from esters: how do you make a tertiary alc

A

Grignard, then H3O+

66
Q

from esters: how do you make a carb acid

A

hydrolysis (acid or base)

67
Q

from esters: how do you make an aldehyde

A

LTTBA
OR
DIBAL then H+

68
Q

from esters: how do you make an amine

69
Q

how can amides be produced

A

from acyl halides, esters, and anhydrides

70
Q

from amides: how do you make a carb acid

A

H2SO4 with heat and time
OR
NaOH and heat then H+

71
Q

from amides: how do you make an amine

A

LAH with Et2O then H+

72
Q

from amides: how do you make a nitrile

A

dehydration (SOCl2)

CHEM 2420- organic chem 2 (10 decks)

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