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Organic Chemistry 2 > Aldehydes & Ketones Continued (Chapter 18) > Flashcards

Aldehydes & Ketones Continued (Chapter 18) Flashcards

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1
Q

Tautomerization of Aldehydes/Ketones

A

The reversible conversion of an aldehyde/ketone to an enol via α-Hydrogen rearrangement and π-electron transfer.

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2
Q

Aldehyde/Ketone → Enol

Enol → Aldehyde/Ketone

A

Tautomerization

This reversible tautomerization process can occur in acidic conditions and basic conditions.

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3
Q

Aldehyde/Ketone → Enolate

A

Base-Catalyzed Deprotonation

Removal of the α-Hydrogen and subsequent π-electron transfer (C=O→C=C) yields the enolate ion.

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4
Q

Enol

A

A compound containing an alcohol group (—OH) adjacent to an alkene group (C=C).

One carbon atom of the alkene is bonded to the alcohol group subsituent.

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5
Q

Enolate

A

An anionic compoundcontaining an alkoxide group (—O–) adjacent to an alkene group (C=C).

One carbon atom of the alkene is bonded to the alkoxide group subsituent.

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6
Q

How is the α-Hydrogen deprotonation of an aldehyde/ketone possible?

A

The α-Hydrogen is highly acidic (i.e. pKa = 16–21)

Resonance stabilization of the deprotonated aldehyde/ketone compound (i.e. an enolate ion) promotes the dissocation of the C—Hα bond.

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7
Q

Reagents: Base-Catalyzed Deprotonation of α-Hydrogen

A

LDA

Lithium Diisopropylamide

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8
Q

α-Hydrogen Deprotonation: Kinetic Control vs. Thermodynamic Control

A
  • Kinetic Control: At low temperatures, the base deprotonates the Iess hindered/substituted α-Hydrogen (to form the less stable enolate ion).
  • Thermodynamic Control: At room/high temperatures, the base deprotonates the more hindered/substituted α-Hydrogen (to form the more stable enolate ion).

While the base is still more likely to initially depronate the less hindered/substituted α-Hydrogen at room/high temperatures (i.e. thermodynamic control), the reversibility of the deprotonation leads to the more stable enolate ion being the predominant product.

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9
Q

Characteristics: Kinetic Control

A
  • Low Temperatures
  • Short Reaction Times
  • Unreversible

The less stable product isomer is the major product.

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10
Q

Characteristics: Thermodynamic Control

A
  • Room/High Temperatures
  • Long Reaction Times
  • Reversible

The more stable product isomer is the major product.

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11
Q

Stability: Aldehye/Ketone vs. Enol

A

An enol is the less stable isomer of an aldehyde/ketone.

In the presence of acid or base, the enol will tauteromize to the more stable aldehyde/ketone isomer.

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12
Q

Methods for Ketone Synthesis

A

2°/3° Enol Tautomerization

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13
Q

Methods for Aldehyde Synthesis

A

0°/1° Enol Tautomerization

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14
Q

Alkyne → Ketone

A

Hg(II)-Catalyzed Hydration

An enol intermediate is formed (but NOT observed) following alcohol-addition and prior to ketone-yielding tautomerization.

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15
Q

Terminal Alkyne → Aldehyde

A

Hydroboration Oxidation

An enol intermediate is formed (but NOT observed) following alcohol-addition and prior to aldehyde-yielding tautomerization.

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16
Q

Reagents: Hg(II)-Catalyzed Alkyne Hydration

A

HgSO4, H2O, H2SO4

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17
Q

Reagents: Hydroboration-Oxidation Alkyne Hydration

A
  1. BH3
  2. H2O2, NaOH
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18
Q

Mechanism: Base-Catalyzed Aldehyde/Ketone Tautomerization

Base-Catalyzed Enolization

A
  1. Deprotonation of the α-Hydrogen (and subsequent π-electron transfer) to yield the Enolate ion.
  2. Protonation of the aldehydic/ketonic Oxygen to yield the Enol.

Product = Enol

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19
Q

Mechanism: Acid-Catalyzed Aldehyde/Ketone Tautomerization

Acid-Catalyzed Enolization

A
  1. Protonation of the aldehydic/ketonic Oxygen to yield the oxocarbenium ion.
  2. Deprotonation of the α-Hydrogen (and subsequent π-electron transfer) to yield the Enol.

Product = Enol

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20
Q

Mechanism: Base-Catalyzed Enol Tautomerization

A
  1. Deprotonation of the enolic alcohol group (—OH) to yield the enolate ion.
  2. π-electron rearrangement to yield the anionic α-Carbon aldehyde/ketone.
  3. Protonation of anionic α-Carbon to yield the (nonionic) aldehyde/ketone.

Product = Aldehyde/Ketone

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21
Q

Mechanism: Acid-Catalyzed Enol Tautomerization

A
  1. Protonation of the enolic alkene group (at the α-Carbon) AND transfer of π-electrons from Oxygen lone pair to Carbon-Oxygen bond (C=O) to yield the oxocarbenium ion.
  2. Depronation of oxocarbenium Oxygen yield the (nonionic) aldehyde/ketone.

Product = Aldehyde/Ketone

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22
Q

Deuterium Exchange of α-Hydrogens

A

All α-Hydrogens of an aldehyde/ketone are replaced with Deuterium isotopes.

The acidic α-Hydrogens are the ONLY hydrogen atoms replaced with Deuterium isotopes.

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23
Q

Reagents: Deuterium Exchange

A

D2O (Excess), OD–

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24
Q

Aldehyde/Ketone → Racemic Mixture

A

Isomerization of Aldehydic/Ketonic α-Stereoisomer

The isomerization reaction yields (1) the* reagent α-Isomer* and (2) its α-Stereoisomer.

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25
Q

Reagents: Isomerization α-Stereoisomer

A

CH3CH2O–, CH3CH2OH

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26
Q

Aldehyde/Ketone → α-Halogenated Aldehyde/Ketone

A

Electrophilic α-Halogenation

This α-halogenation reaction can occur in acidic conditions and basic conditions.

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27
Q

Reagents: Acid-Catalyzed α-Halogenation

A

X2, CH3CO2H, H2O (Solvent)

Electrophile = X2
Acid Catalyst = CH3CO2H

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28
Q

Reagents: Base-Catalyzed α-Halogenation

A

X2, NaOH, H2O (Solvent)

Electrophile = X2
Acid Catalyst = NaOH

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29
Q

Why do enols react faster with electrophiles than simple alkenes?

A

The alkene group of enols is more electron-rich than that of simple alkenes.

Since the alcohol substituent of the enol is electron-donating, the adjacent alkene group (i.e. α-Carbon) possesses a greater electron density (than a simple alkene).

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30
Q

Why do enolates react faster with electrophiles than simple alkenes?

A

The alkenyl α-Carbon of enols is more electron-rich than that of simple alkenes.

The enolate possesses an anionic α-Carbon resonance form, so the alkenyl α-Carbon possesses a greater electron density (than it would on a simple alkene).

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31
Q

Enolization Reactions: Acid-Catalyzed vs. Base-Catalyzed

Tautomerization

A
  • Acid-Catalyzed: Protonation of the aldehydic/ketonic Oxygen (to form an oxocarbenium ion) occurs first.
  • Base-Catalyzed: Deprotonation of the α-Hydrogen (to form an enolate ion) occurs first.
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32
Q

Carbonylization Reactions: Acid-Catalyzed vs. Base-Catalyzed

Tautomerization

A
  • Acid-Catalyzed: Protonation of the α-Hydrogen (to form an oxocarbenium ion) occurs first.
  • Base-Catalyzed: Deprotonation of the aldehydic/ketonic Oxygen (to form an enolate ion) occurs first.
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33
Q

What conditions will cause the tautomerization of enols

A

Enols will tautomerize in the presence of acid or base.

A minor amount of acid or base is sufficient to catalyze the transformation from the less-stable enol to the more-stable ketone/aldehyde.

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34
Q

Products of α-Halogenation: Acid-Catalyzed vs. Base Catalyzed

α-Halogenation of Aldehyde/Ketone

A
  • Acid-Catalyzed: Monohalogenated Product
  • Base-Catalyzed: Trihalogenated/Polyhalogenated Product

Under basic conditions, the α-Halogenation of aldehydes/ketones CANNOT be stopped at the monohalogenated stage.

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35
Q

Why is it NOT possible to stop base-catalyzed a-Halogenation at the monohalogenated stage?

α-Halogenation of Aldehydes/Ketones

A

The C—Hα bonds of the monohalogenated product are weaker (i.e. the α-Hydrogens are more acidic) than the C—Hα bonds of the starting material (due to the electron-withdrawing effect of the halogen).

The monohalogenated product will react faster with the halogen electrophile (X2) than the starting material did. (Each further-halogenated stage will react increasingly faster with the halogen electrophile to eventually halogenate all C—Hα bonds.)

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36
Q

Why is it possible to achieved the monohalogenated α-Halogenation product?

α-Halogenation of Aldehydes/Ketones

A

The alkenyl group of the tautomerized monohalogenated product is less electron-dense (i.e. less reactive) than the alkenyl group of the tautomerized starting material (due to the electron-withdrawing effect of the halogen).

The alkenyl group of the tautomerized monohalogenated product will attack the halogen electrophile (X2) slower than the alkenyl group of the starting material did.

37
Q

Reagents: Carbonyl α-Alkylation

α-Alkylation of Aldehydes/Ketones

A
  1. LDA
  2. R—X
38
Q

Aldehyde/Ketone → α-Alkylated Aldehyde/Ketone

A

Enamine α-Alkylation

Enamine α-Alkylation does NOT result in poly-α-alkylation and can be used to α-alkylate aldehydes AND ketones.

(Carbonyl α-Alkylation is rarely useful/practical for the synthesis of α-alkylated products.)

39
Q

Reagents: Enamine α-Alkylation

α-Alkylation of Aldehydes/Ketones

A
  1. 2° Amine
  2. R—X
  3. H2O
40
Q

Why is Carbonyl α-Alkylation is rarely useful/practical for the synthesis of α-alkylated products?

A

Many competing side reactions can potentially occur (e.g. E2 Elimination, Poly-α-Alkylation; Aldehyde Condensation) when the carbonyl α-Alkylation reagents are combined.

A more practical/useful alternative to carbonyl α-Alkation is enamine α-Alkylation.

41
Q

α,β-Unsaturated Carbonyl Compound

A
  • α,β-Unsaturated Aldehyde: A planar compound containing an aldehyde group in conjugation with an alkenyl group.
  • α,β-Unsaturated Ketone: A planar compound containing a ketone group in conjugation with an alkenyl group.

The π-electrons of the carbon-oxygen double bond (C=O) are in conjugation with the π-electrons of the adjacent carbon-carbon double bond (C=C).

42
Q

2 Aldehyde → α,β-Unsaturated Aldehyde

Di-α-Hydrogen Aldehydes OR Tri-α-Hydrogen Aldehydes

A

Aldol Condensation

  • A trans carbon-carbon double bond (C=C) is formed between one aldehyde’s α-carbon and the other aldehyde’s carbonyl carbon.
43
Q

Reagents: Aldol Condensation

Starting Material: 2 Aldehyde (Identical)

A

NaOH, Heat (Δ)

44
Q

Aldol

A

A compound containing an aldehyde group and an alcohol group (—OH) on the β–carbon.

45
Q

What is the driving force for the dehydration step of Aldol Condensation?

A

The formation of the π-conjugated system within the α,β-unsaturated aldehyde.

The charge delocalization of the π-conjugated system confers great stability to the unsaturated aldehyde product.

46
Q

2 Aldehyde → Aldol

Mono-α-Hydrogen Aldehydes

A

Aldol Condensation

2 Aldehyde → Aldol = Intramolecular

47
Q

Why are aldehydes containing zero α-hydrogens unable to undergo Aldol Condensation?

A

The aldehyde cannot be deprotonated at the α-position to yield an enolate.

48
Q

Why are intermolecular Aldol Condensation reactions with ketone reagents thermodynamically unfavorable?

A

The carbonyl carbon of the ketone is stabilized via hyperconjugation from adjacent alkyl groups, so it is less electron-deficient and less prone to nucleophilic attack.

49
Q

Why do intramolecular Aldol Condensation reactions occur faster than intermolecular reactions?

A

The intramolecular Aldol Condensation reaction exhibits favorable entropic effects (i.e. the starting reagent forms the α,β-unsaturated aldehyde and H2O).

50
Q

Why are intermolecular Aldol Condensation reactions with ketone reagents possible?

A

The intramolecular Aldol Condensation reaction exhibits favorable entropic effects (i.e. the starting reagent forms the α,β-unsaturated aldehyde and H2O).

The positive entropic effects of the condensation reaction override its negative thermodynamic effects.

51
Q

Synthesis Mechanisms: α,β-Unsaturated Aldehyde

A
  • Aldol Condensation
  • Allylic Alcohol Oxidation
52
Q

α,β-Unsaturated Carbonyls as Simple Alkenes

A

An α,β-unsaturated aldehyde/ketone will react as a simple alkene if NONE of the other reagents are nucleophiles.

The alkenyl group of the α,β-unsaturated aldehyde/ketone is NOT involved in the reaction.

53
Q

Reactions: α,β-Unsaturated Carbonyls as Simple Alkenes

A
  • Metal-Catalyzed Hydrogenation of Alkene
  • Electrophilic Halogenation of Alkene
  • Diels-Alder Reaction
54
Q

α,β-Unsaturated Carbonyls as Simple Aldehydes/Ketones

1,2-Addition

A

An α,β-unsaturated aldehyde/ketone will react as a simple aldehyde/ketone if it reacts with any nucleophilic organometallic, metal-hydride, hydroxylamine, or hydrazine compound.

The nucleophilic compound attacks the α,β-unsaturated aldehyde/ketone at the carbonyl carbon (and does NOT interact with the alkenyl group).

55
Q

Reactions: α,β-Unsaturated Carbonyls as Simple Aldehydes/Ketones

A
  • Grignard Reactions
  • Organolithium Reactions
  • Metal-Hydride Reduction
  • Nucleophilic Hydroxylamine Addition
  • Nucleophilic Hydrazine Addition
56
Q

Hydroxylamine

A

NH2OH

57
Q

1,2–Addition

Addition to α,β-Unsaturated Carbonyl

A

The α,β-unsaturated carbonyl acts as a simple aldehyde/ketone.

The nucleophilic compound attacks the α,β-unsaturated aldehyde/ketone at the carbonyl carbon (and does NOT interact with the alkenyl group).

58
Q

1,4–Addition

Conjugate Addition

A

The alkenyl group AND the aldehyde/ketone group of the α,β-unsaturated carbonyl are involved in the addition reaction.

The nucleophilic compound attacks the α,β-unsaturated aldehyde/ketone at the β–carbon to create an enol intermediate.

59
Q

Nucleophiles: 1,2–Addition

A
  • H2O
  • Alcohols
  • Thiols
  • 1°/2° Amines
  • Cyanides
  • Organocuprates
  • Grignard Reagents
  • Enolates

The 1,2–Addition pathway is preferred by stronger nucleophiles. (Hydroxylamine and Hydrazine are EXCEPTIONS!)

60
Q

Nucleophiles: 1,4–Addition

A
  • Grignard Reagents
  • Organolithiums
  • Metal Hydrides
  • Hydroxylamine
  • Hydrazine

The 1,4–Addition pathway is preferred by weaker nucleophiles. (Hydroxylamine and Hydrazine are EXCEPTIONS!)

61
Q

α,β-Unsaturated Carbonyls as Alkenyls and Aldehydes/Ketones

A

The α,β-unsaturated aldehyde/ketone experiences 1,4-addition if it reacts with a weaker nucleophilic compound.

The weaker nucleophilic compound attacks the α,β-unsaturated aldehyde/ketone at the β–carbon to create an enol intermediate. Subsequent deprotonation and π-electron rearragement results in the formation of a simple aldehyde/ketone.

62
Q

Why are Grignard reagents able to attack at the α,β-unsaturated carbonyl at the β–carbon OR the carbonyl carbon?

A

Grignard reagents are medium-strength nucleophiles (i.e. weaker nucleophiles than organolithium reagents and stronger nucleophiles than organocuprate reagents).

Since the Grignard reagent is a weaker nucleophile than the 1,2–preferring organolithium reagent and a stronger nucleophile than the 1,4–preferring organocurprate reagent, it has the ability to perform both types of nuclephilic addition.

63
Q

Reactions of α,β-Unsaturated Carbonyls: Grignard Reagents

Nucleophilic Addition to α,β-Unsaturated Carbonyls

A

Grignard reagents can undergo 1,2-addition AND 1,4-addition to α,β-unsaturated aldehydes/ketones.

Grignard reagents are weaker nucleophiles than the 1,2–preferring organolithium reagents and stronger nucleophiles than the 1,4–preferring organocurprate reagents.

64
Q

Why do stronger nucleophiles prefer to undergo 1,2–Addition?

Nucleophilic Addition to α,β-Unsaturated Carbonyls

A
  • The carbonyl carbon is more positively charged than the β-carbon, so the nucleophile will attack the carbonyl carbon faster/earlier.
  • Attack of the stronger nucleophilic compound is highly exothermic due to the formation of the robust C—Nu bond, so the reaction is irreversible.

The carbonyl carbon has a greater partial positive charge (than the β-carbon) since it is directly bonded to the electronegative Oxygen aotm.

65
Q

1,2–Addition: Thermodynamic Control vs. Kinetic Control

Nucleophilic Addition to α,β-Unsaturated Carbonyls

A

Kinetic Control

The nucleophile will always attack the carbonyl carbon first due to it possessing a greater partial positive charge. (Unless the nucleophilic addition reaction is reversible, the less stable 1,2-addition product will predominate.)

66
Q

1,4–Addition: Thermodynamic Control vs. Kinetic Control

Nucleophilic Addition to α,β-Unsaturated Carbonyls

A

Thermodynamic Control

Although the nucleophile will always attack the carbonyl carbon first, the addition reaction becomes reversible under thermodynamic control. (The thermodynamically more stable 1,4-addition product will predominate since any 1,2-addition reaction will be reversible.)

67
Q

Addition to α,β-Unsaturated Carbonyls: Hydroxylamine and Hydrazine

A

Hydroxylamine and Hydrazine prefer to undergo 1,2–addition to the α,β-unsaturated aldehyde/ketone (despite being weaker nucleophiles) since the 1,2–product is thermodynamically more stable.

The Oxime (i.e. the 1,2-addition product of Hydroxylamine) and Hydrazone (i.e. the 1,2-addition product of Hydrazine) are stabilized via conjugation between the OH/NH2 π-electrons and the C=N π-bond.

68
Q

During the protonation step of 1,4–addition, why does the enolate become protonated faster than the α-carbon?

Nucleophilic Addition to α,β-Unsaturated Carbonyls

A

The enolate (with a full negative charge) is more negatively charged than the α–carbon (with a partial negative charge).

69
Q

Oxime

A

A compound containing a Carbon double-bonded to a Nitrogen (C=N) that is single-bonded to an alcohol group (—OH).

R2—C=N—OH

70
Q

Reagents: Organocuprate Preparation

Organocuprate = R2CuLi

A

2 R—Li + CuI

71
Q

Reactions of Organocuprates

A
  • β–Alkylation (via Acid Workup)
  • α,β–Dialkylation (via Addition of Alkyl Halide)
72
Q

α,β-Unsaturated Carbonyl → 1,5-Dicarbonyl

A

Michael Addition

The Michael Addition reaction occurs under basic conditions ONLY.

73
Q

Aldehyde/Ketone → 1,5-Dicarbonyl

A

Michael Addition

The Michael Addition reaction occurs under basic conditions ONLY.

74
Q

Reagents: Michael Addition

Starting Materials: α,β-Unsaturated Carbonyl + Aldehyde/Ketone

A

CH3CH2O–, CH3CH2OH

The α,β-unsaturated carbonyl must consist of four carbons.

75
Q

Ethoxide Deprotonation in Michael Addition

A

Since the ethoxide base is relatively unhindered, it will deprotonate the most substituted α-carbon (to form the most stable enolate intermediate).

76
Q

α,β-Unsaturated Carbonyl → Cyclic α,β-Unsaturated Ketone

A

Robinson Annulation

The Robinson Addition mechanism occurs under basic conditions and at high temperatures ONLY.

77
Q

Aldehyde/Ketone → Cyclic α,β-Unsaturated Ketone

A

Robinson Annulation

The Robinson Addition mechanism occurs under basic conditions and at high temperatures ONLY.

78
Q

Mechanism: Robinson Annulation

A
  1. Deprotonation of α-Carbon to Aldehyde/Ketone
  2. 1,4–Addition of Enolate to α,β-Unsaturated Carbonyl
  3. Protonation of Internal α-Carbon to Enolate
  4. Deprotonation of Terminal α-Carbon to Ketone
  5. Ring Formation via Attack by Terminal α-Carbon of Enolate
  6. Protonation of Oxide
  7. Deprotonation of α-Carbon to Ketone
  8. Leaving of Hydroxyl via π-Electron Rearragement

Michael Addition + Intramolecular Aldol Condensation

79
Q

Reagents: Robinson Annulation

Starting Materials: α,β-Unsaturated Carbonyl + Aldehyde/Ketone

A
  1. CH3CH2O–, CH3CH2OH
  2. CH3CH2O–, Δ (Heat)

The α,β-unsaturated carbonyl must consist of four carbons.

80
Q

1,5-Dicarbonyl → Cyclic α,β-Unsaturated Ketone

Step 2 of Robinson Annulation

A

Intramolecular Aldol Condensation

81
Q

[4 + 2] Annulation

A

Robinson Annulation

The addition of an aldehyde/ketone to a four-carbon α,β-unsaturated carbonyl yields a six-membered cyclic α,β-unsaturated carbonyl.

82
Q

In what cases can Robinson Annulation NOT occur?

A

Robinson Annulation is impossible in cases where NO α-Hydrogens to the non-cyclic ketone are present.

E.g. Robinson Annulation is impossible with compounds containing a phenol group adjacent to the non-cyclic ketone.

83
Q

Synthons with Nucleophilic α-Carbon

A
  • Enol
  • Enolate
  • Enamine
  • Phosphorus Ylide
84
Q

Synthons with Electrophilic β-Carbon

A
  • α,β-Unsaturated Aldehyde
  • α,β-Unsaturated Ketone
85
Q

Synthons with Carbanion

A
  • Grignard Reagents
  • Organolithium Reagents
  • Organocupric Reagents
  • Cyanides
86
Q

Synthons with Carbocation

A
  • Alkyl Halides
  • Epoxides
87
Q

Examples: Carbon-Nucleophiles

A
  • Enol
  • Enolate
  • Enamine
  • Grignard Reagent
  • Organolithium Reagent
  • Organocupric Reagent
  • Cyanide
  • Phosphorus Ylide
88
Q

Examples: Carbon-Electrophiles

A
  • Alkyl Halide
  • Aldehyde (Carbonyl Carbon)
  • Ketone (Carbonyl Carbon)
  • α,β-Unsaturated Aldehyde (β-Carbon)
  • α,β-Unsaturated Ketone (β-Carbon)
  • Epoxide
  • Imine
  • Iminium
89
Q

Protection Groups

A
  • Aldehyde/Ketone: Acetal OR Thioacetal
  • Hydroxyl Group: Ether
  • Amine: Amide

Organic Chemistry 2 (12 decks)

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