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Orgo II > Exam 3: 21, 22, 23 > Flashcards

Exam 3: 21, 22, 23 Flashcards

(52 cards)

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1
Q

Carboxylic Acid Derivatives

A

Acid chloride - Acid Anhydride - Ester - Amide

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2
Q

Carboxylic Acid Derivatives

A

Acid chloride - Acid Anhydride - Ester - Amide

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3
Q

Rules for Carboxylic Rxns

A

Can hydrolyze (H2O/H3O+) to a carboxylic acid to go from less reactive to more reactive

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4
Q

Acid Chloride - Synthesis from Carboxylic Acid

A

NTK a synthesis
NTK mechanism

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5
Q

Acid Chloride - Hydrolysis (to carboxylic acid)

A
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6
Q

Acid Chloride - Reduction

A

LiAlH4 - very reactive so will immediately react again

Remember water is reacted separately otherwise it would react in the first reaction

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7
Q

Acid Chloride - Grignard Reagent

A

MgBr- very reactive so will immediately react again

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8
Q

Acid Anhydride - Synthesis from carboxylic acid

A

NTK a synthesis
NTK mechanism

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9
Q

Acid Anhydride - Synthesis from acid chloride

A

NTK a synthesis
NTK mechanism

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10
Q

Ester Rxns - Synthesis from Carboxylic Acid (Fisher Esterfication)

A

NTK mechanism - Only rxn that uses reverse arrows. Any strong acid.

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11
Q

Ester Rxns - Synthesis from acid chloride

A

NTK mechanism

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12
Q

Ester Rxns - Synthesis from acid anhydride

A

NTK mechanism

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13
Q

Ester Rxns - Intramolecular esterfication

A
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14
Q

Ester Rxns - Hydrolysis Acid Promoted

A
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15
Q

Ester Rxns - Hydrolysis Base Promoted aka Saponification

A

NTK mechanism
May say (aq) which just means its in water (may not say water)
Reaction continues forward with -OH
Eventually makes salt (carboxylate ion) (hence Na+)

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16
Q

Ester Rxns - Reduction

A

Remember reaction continues bc LiAlH4 is very reactive

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17
Q

Ester Rxns - Grignard Reagent

A

Remember reaction continues bc MgBr is very reactive
Remember O ends up in the middle

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18
Q

Amide Rxns - Synthesis from Carboxylic Acid

A

NTK mechanism

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19
Q

Amide Rxns - Synthesis from acid chloride

A

NTK mechanism

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20
Q

Amide Rxns - Synthesis from acid anhydride

A

NTK mechanism

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21
Q

Amide Rxns - Synthesis from ester

Study These Flashcards
A

NTK mechanism

22
Q

Amide Rxns - Intramolecular amide formation

23
Q

Amide Rxns - Gillman Reagent

24
Q

Amide to Anhydride

25
Acid chloride to Amide
26
alpha-carbon: enols and enolates
normally carbons pka ~30 (more basic)
27
Tautomerism
Enol will always have the double bond between the alpha carbon and -OH
28
Taut: Base-catalyzed enol formation
29
Taut: Acid-catalyzed enol formation
30
Halogenation of aldehyde - acid catalyzed
31
Halogenation of aldehyde - base catalyzed
32
alpha-Halogenation of a carboxylic acid Hell-Volhard-Zelinki Rxn
33
alpha-Alkylation of aldehydes and ketones
34
Malonic Ester Synthesis
1. Base 2. SN2 3. Base 4. SN2 5. Hydrolysis 6. Heat
35
Acetoacetic Ester Synthesis
1. Base 2. SN2 3. Base 4. SN2 5. Hydrolysis 6. Heat
36
Haloform Rxn
Must be a methy ketone X=Halogen
37
Aldol condensation
Aldehyde (starting molecule) and alcohol rxn Reacts with base to create enolate Remember to identify alpha carbon
38
Crossed aldol condensation
One reactant must have no alpha-hydrogens (ie aldehyde with benzene ring) Always add to the structure that doesnt have alpha-hydrogen LDA strong base so arrows are forward H-N is the LDA molecule No LDA with H2O
39
Intramolecular aldol condensation
Look for molecule with 2 aldehydes Reacts with hydroxide or LDA Number carbons from the enolate carbon and count 6 (benzene) Results in alpha beta unsatrurated aldehyde
40
Claisen condensation
Claisen means with an ester (with one alpha carbon) so always starting molecule. On exam may just provide the reactn Reversible arrows Condensation rxns means its condensing with itself unless its "crossed" Lone pairs between 2 carbonyl molecules means 2 resonance structures
41
Crossed claisen condensation
Et in OEt means ethyl
42
Intramolecular claisen condensation
43
Conjugate addition
44
Micheal Addition
45
Aldol Condensation
46
Crossed Aldol Condensation
47
Intramolecular aldol condensation
48
Claisen condensation
49
Crossed claisen condensation
50
Intramolecuiar claisen condensation
51
Conjugate addition
Condensation then addition Always add to B caron unless ypu have a grignard reagent (EtMgBr/H2O) in which it will undergo direct additon, adding directly to the carbonyl group
52
Michael Addition

Orgo II (10 decks)

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