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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
product of C type?
cyanohydrin
26
product of grignard?
alcohol and a new CC bond
27
product of wittig?
new C=C bond
28
product of cannizzaro?
acid and alcohol (50/50)
29
product of baeyer villager?
ester (or carb acid if one R group is an H)
30
with carbonyls: how to make an alcohol
``` H type (LAH then water, or NaBH4 and water) OR grignard OR cannizzaro (will also make acid) ```
31
with carbonyls: how to make a ketal or acetal
O type (H+ and ROH)
32
with carbonyls: how to make a geminal diol
hydrate a carbonyl (acidic or basic)
33
with carbonyls: how to make a ketone
S type with hydrolysis
34
with carbonyls: how to make a hydrocarbon
``` S type with desulfurization OR clemmensen OR Wolff-kishner ```
35
with carbonyls: how to make an imine
N type with 1o amine
36
with carbonyls: how to make an enamine
N type with 2o amine
37
with carbonyls: how to make a cyanohydrin
C type
38
with carbonyls: how to make a new C=C bond
Wittig
39
with carbonyls: how to make a carb acid
cannizzaro (will also make alcohol) OR baeyer villager (if R=H)(two possible products)
40
with carbonyls: how to make an ester
baeyer villager (this could be an acid if R=H)
41
with carbonyls, how do you make a new C-C bond
S type, Grignard
42
with carbonyls, how do you get a new C=C bond
Wittig
43
in regards to electron withdrawing substituents, how do you increase acidity of acids
more electron withdrawing subs increases acidity
44
how do you make a carb acid from alcohols
oxidation of 1o alc
45
how do you make a carb acid from an aldehyde
oxidation of a 2o alc | HNO3 or Tollens
46
how do you make a carb acid from an alkyne
oxidation
47
how do you make a carb acid from a nitrile
hydrolysis (acidic or basic)
48
how do you make a carb acid from an acyl halide
grignard with carbon dioxide
49
from a carb acid: how do we make an alcohol
reduction (LAH then water)
50
from a carb acid: how do we make an aldehyde
reduction to an alcohol, then PCC
51
from a carb acid: how do we make a carboxylic acid derivative
react with LG then Nuc
52
how do we make an acyl halide
carb acid reacts SOCl2 (LG), then nuc (HCl)
53
from an acyl halide: how do we product a tertiary alc
C type (grignard)
54
from an acyl halide: how do we product a primary alc
H type (LAH)
55
from an acyl halide: how do we product an aldehyde
LTTBA then H+
56
from an acyl halide: how do we product a ketone
lithium dialkyl cuprates
57
from an acyl halide: how do we product an amine
with R2NH
58
from an acyl halide: how do we product an ester
ROH
59
how do we make anhydrides
acyl halide + carb acid
60
from anhydrides: how do we make carb acids and carbonyls
react with any nuc
61
what is the name for ester formation
transesterification
62
how do you make esters from carb acids
ROH and H+
63
how do you convert esters back into carb acids
hydrolysis
64
from esters: how do you make a primary alc
LAH then H3O+
65
from esters: how do you make a tertiary alc
Grignard, then H3O+
66
from esters: how do you make a carb acid
hydrolysis (acid or base)
67
from esters: how do you make an aldehyde
LTTBA OR DIBAL then H+
68
from esters: how do you make an amine
RNH2
69
how can amides be produced
from acyl halides, esters, and anhydrides
70
from amides: how do you make a carb acid
H2SO4 with heat and time OR NaOH and heat then H+
71
from amides: how do you make an amine
LAH with Et2O then H+
72
from amides: how do you make a nitrile
dehydration (SOCl2)

CHEM 2420- organic chem 2 (10 decks)

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