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Organic Chemistry Reaction Mechanisms > Exam 3 > Flashcards

Exam 3 Flashcards

(55 cards)

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1
Q

conditions for enolate to enol

A

H+

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2
Q

intramolecular aldol condensation

A

NaOEt, HOEt

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3
Q

crossed aldol condensation

A

NaOEt, HOEt

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4
Q

why can “crossed” aldol condensations only be used in limited cases?

A
  1. only one reaction partner is enolizable
  2. electrophlile must be used in excess to avoid self aldol
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5
Q

acidic aldol condensation

A

H3O+

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6
Q

retro aldol

A

alpha-beta unsaturated from enolate + carbonyl

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7
Q

what is the signature product of a claisen condensation?

A

beta-keto ester

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8
Q

ester to beta-keto ester

A
  1. NaOR’, R’OH
  2. H+ workup
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9
Q

what MUST be present in the starting ester to perform a classien condensation?

A

the starting ester must have 2 alpha protons

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10
Q

conditions for a retro claisen

A

NaOR, ROH

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11
Q

conditions for intramolecular claisen condensation

A
  1. NaOR, ROH
  2. H+ workup
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12
Q

how do we get this desired product in steps?

A
  1. enolize a dicarbonyl compound
    2.alkylation at the alpha carbon
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13
Q

conditions for hydrolysis and decarboxylation of beta-ketone esters

A

1.NaOH, H2O
2.HCI, heat

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14
Q

what reaction occurs between a delocalized enolate (nuc) and an alpha-beta unsat’d carbonyl (elec)

A

micheal reaction

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15
Q

what is the signature product of a Micheal reaction?

A

1,5-dicarbonyl

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16
Q

conditions for a micheal reaction

A

1.NaOR, ROH
2.H+ w/u

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17
Q

steps for carbonyl to enol in acid

A
  1. protonate oxygen
  2. deprotonate H and delocalize it to oxygen
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18
Q

steps for carbonyl to enol in base

A
  1. base with deprotonate and delocalize e- onto the oxygen
  2. protonation by weak acid (water)
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19
Q

what is the intermediate for aldol condensation?

A

beta-hydroxy carbonyl

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20
Q

conditions aldehyde/ketone to imine

A

RNH2 ph=5

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21
Q

conditions aldehyde/ketone to enamine

A

R2NH2 ph=5

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22
Q

conditions for imine to aldehyde

A

H3O+ (hydrolysis)

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23
Q

conditions for enamine to ketone

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A

H3O+ (hydrolysis)

24
Q

conditions for ester to cbx acid

Study These Flashcards
A

1.NaR
2.H+ workup

25
conditions for acid halide to cbx acid
H2O
26
what are two good enough LGs to get kicked out by LPP but not for Sn2 or E2
-OH or -OR
27
conditions for amide to cbx acid
H2O, H+ cat (acidic conditions)
28
conditions for nitrile to cbx acid
H2O, H+ cat (acidic conditions)
29
conditions for cbx acid to acid chlorides
SOCI2 (basic conditions)
30
conditions for cbx acid to ester
ROH, H+ (cat) (acidic conditions)
31
what conversion happens in a Fisher Esterification?
cbx acid to ester
32
conditions for acid chloride to amide
R-NH2, pyr
33
conditions for acid chloride to ester
ROH
34
what types of reagents when added to esters will act like nucleophiles and be added twice
organometallic or hydride reagents
35
what kind of functional groups are reactive with Grignards?
ketones
36
conditions for reduction of esters and acids
1. LiALH4, Et2O 2. H+ workup
37
conditions for amide to amine
1. LiALH4, Et2O 2. H+ workup
38
conditions for nitrile to amine
1. LiALH4, Et2O 2. H+ workup
39
conditions for primary alcohol to aldehyde
CrO3, pyr
40
conditions for primary alcohol to cbx acid
CrOs, H2O
41
conditions for secondary alcohol to ketone
CrO3, pyr
42
why cant a tertiary alcohol go through oxidation?
there are no hydrogens to remove
43
why are aldehydes more electrophilic than ketones?
Hyperconjugation! delocalization of the sigma C-H electrons to pi*C=O
44
what are two hydride reducing reagents to go from aldehyde/ketone to secondary alcohol
NaBH4,ROH or 1. LiAlH4, Et2O 2. H+ workup
45
what are two organometallic nucleophilic reagents to go from aldehyde/ketone to secondary alcohol
1.R''Li, Et2O 2. H+ w/u or 1.R''MgX, Et2O 2. H+ w/u
46
conditions for hydrate formation in acid
H2O, H+cat
47
conditions for hydrate formation in base
NaOH, H2O
48
conditions for carbonyl group to cyanohydrin
NaCN, H2O
49
conditions for formation of hemiacetals under basic conditions
NaOR, ROH
50
conditions for formation of acetals under acidic conditions
ROH, H+ cat
51
conditions for formation of cyclic acetals under acidic conditions
OH-c-c-OH , H+ (cat)
52
1,2 addition favors what kind of nucleophiles?
hard
53
1,4 addition favors what kind of nucleophiles?
soft
54
conditions for cyclic acetals to cbx acid
H3O+
55
what is the purpose of KOtBu, tBuOH?
to pull off protons

Organic Chemistry Reaction Mechanisms (2 decks)

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