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Organic Chemistry Reaction Mechanisms > Exam 3 > Flashcards

Exam 3 Flashcards

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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

A

H3O+ (hydrolysis)

24
Q

conditions for ester to cbx acid

A

1.NaR
2.H+ workup

25
Q

conditions for acid halide to cbx acid

A

H2O

26
Q

what are two good enough LGs to get kicked out by LPP but not for Sn2 or E2

A

-OH or -OR

27
Q

conditions for amide to cbx acid

A

H2O, H+ cat (acidic conditions)

28
Q

conditions for nitrile to cbx acid

A

H2O, H+ cat (acidic conditions)

29
Q

conditions for cbx acid to acid chlorides

A

SOCI2 (basic conditions)

30
Q

conditions for cbx acid to ester

A

ROH, H+ (cat) (acidic conditions)

31
Q

what conversion happens in a Fisher Esterification?

A

cbx acid to ester

32
Q

conditions for acid chloride to amide

A

R-NH2, pyr

33
Q

conditions for acid chloride to ester

A

ROH

34
Q

what types of reagents when added to esters will act like nucleophiles and be added twice

A

organometallic or hydride reagents

35
Q

what kind of functional groups are reactive with Grignards?

A

ketones

36
Q

conditions for reduction of esters and acids

A
  1. LiALH4, Et2O
  2. H+ workup
37
Q

conditions for amide to amine

A
  1. LiALH4, Et2O
  2. H+ workup
38
Q

conditions for nitrile to amine

A
  1. LiALH4, Et2O
  2. H+ workup
39
Q

conditions for primary alcohol to aldehyde

A

CrO3, pyr

40
Q

conditions for primary alcohol to cbx acid

A

CrOs, H2O

41
Q

conditions for secondary alcohol to ketone

A

CrO3, pyr

42
Q

why cant a tertiary alcohol go through oxidation?

A

there are no hydrogens to remove

43
Q

why are aldehydes more electrophilic than ketones?

A

Hyperconjugation!
delocalization of the sigma C-H electrons to pi*C=O

44
Q

what are two hydride reducing reagents to go from aldehyde/ketone to secondary alcohol

A

NaBH4,ROH
or
1. LiAlH4, Et2O
2. H+ workup

45
Q

what are two organometallic nucleophilic reagents to go from aldehyde/ketone to secondary alcohol

A

1.R’‘Li, Et2O
2. H+ w/u
or
1.R’‘MgX, Et2O
2. H+ w/u

46
Q

conditions for hydrate formation in acid

A

H2O, H+cat

47
Q

conditions for hydrate formation in base

A

NaOH, H2O

48
Q

conditions for carbonyl group to cyanohydrin

A

NaCN, H2O

49
Q

conditions for formation of hemiacetals under basic conditions

A

NaOR, ROH

50
Q

conditions for formation of acetals under acidic conditions

A

ROH, H+ cat

51
Q

conditions for formation of
cyclic acetals under acidic conditions

A

OH-c-c-OH , H+ (cat)

52
Q

1,2 addition favors what kind of nucleophiles?

A

hard

53
Q

1,4 addition favors what kind of nucleophiles?

A

soft

54
Q

conditions for cyclic acetals to cbx acid

A

H3O+

55
Q

what is the purpose of KOtBu, tBuOH?

A

to pull off protons

Organic Chemistry Reaction Mechanisms (2 decks)

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