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Chem 352 > Exam 3 > Flashcards

Exam 3 Flashcards

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0
Q

Fischer Esterification

A

Creates an ester from Carboxylic acid

Uses: acid

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1
Q

What does the Hoffman elimination do?

A

Turns an amine into an alkene, and forms the less substituted alkene (anti-Zaitsev) product

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2
Q

What does saponification do?

A

Hydrolysis of ester under basic conditions to form carboxylate anions
Last step is irreversible

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3
Q

What does hydrolysis of a nitrile in acid (or base) produce?

A

Carboxylic acid (or carboxylate anion)

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4
Q

What reagents synthesize nitriles?

A

R-X and CN-

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5
Q

What is the order of decreasing reactivity for the reagents used in Nu Acyl substitution rxns?

A

Acid chloride > anhydride > ester ~ Carboxylic acid > amide

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6
Q

What reagent is used to convert COOH to acid chloride?

A

SOCl2 and heat

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7
Q

What reagent is used to convert COOH to an anhydride?

A

Heat

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8
Q

What reagent is used to convert COOH to an ester?

A

HOR’ and H+ cat.

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9
Q

What reagent is used to convert COOH to an amide?

A

NH2R’ and DCC

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10
Q

What reagent is used to convert acid chloride to COOH?

A

H2O and pyridine

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11
Q

What reagent is used to convert anhydrides, esters, or amides to COOH?

A

H2O and H+

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12
Q

What reagent is used to convert ester to COOH?

A

H2O and H+ (or base)

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13
Q

What does the haloform reaction do?

A

Forms a good LG (which leaves as the haloform)

Forms a carboxylate anion

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14
Q

What three things allow you to preferentially make the kinetic enolate over the thermodynamic enolate?

A 
Strong, BULKY base (LDA)
Aprotic solvent (like THF)
Low temp (-78 C)
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15
Q

What does Malonic ester synthesis do?

A

Uses a Malonic ester to synthesize Carboxylic acid and CO2
1-Deprotonate to form enolate
2-Alkylation via R-X
3-Hydrolysis and loss of CO2 (or more if it is bonded to that LG)

16
Q

What does adetoacetic ester synthesis do?

A

Makes methyl ketones

Steps are identical to Malonic ester synthesis

17
Q

What does Aldol reaction do?

A

Forms C-C bonds using aldehydes or ketones as starting material
1-Form Nu enolate
2-Nu addition
3-Protonation

18
Q

When can decarboxylation occur?

A

Whenever a carboxy group is bonded to the alpha carbon of another carbonyl group

19
Q

What do intramolecular Aldol reactions do?

A 
Form five and six member rings
1-Make enolate
2-Nu attacks
3-New C-C bond forms
4-H2O is lost and pi bond forms
20
Q

What does the Claisen reaction do?

A

Makes new C-C bonds between the alpha carbon and carbonyl carbon of two esters via substitution
1-Make enolate
2-Nu addition and loss of LG
3-deprotonation and protonation

21
Q

What will a 1,6 diester make if it reacts with itself via a Claisen reaction?

A

A five-member ring

22
Q

What does a Michael reaction do?

A

1,4 addition of enolate to beta carbon of alpha, beta unsaturated carbonyl system
1-Enolate forms
2-Enolate attacks BETA carbon
3-Alpha carbon is protonated

23
Q

What does the Robinson Annulation do?

A

Forms a six-member ring and three new C-C bonds
1-Michael reaction
2-the other enolate is formed
3-Nu attacks other carbonyl carbon to make ring
4-Beta oxygen gets protonated
5-dehydration and new pi bond forms between alpha and beta carbons (this step is irreversible)

24
Q

When using a diazonium salt what reagent is used to make phenol?

A

H2O

25
Q

When using a diazonium salt what reagent is used to make benzyl chlorides or bromides?

A

CuCl

CuBr

26
Q

When using a diazonium salt what reagent is used to make benzyl fluorides?

A

HBF4

27
Q

When using a diazonium salt what reagent is used to make benzyl iodides?

A

NaI or KI

28
Q

When using a diazonium salt what reagent is used to make benzene?

A

H3PO2

29
Q

When using a diazonium salt what reagent is used to make cyanobenzene?

A

CuCN

30
Q

How can you selectively make a primary amine?

A

Gabriel synthesis

31
Q

What are the steps of reductive amination of aldehydes and ketones?

A

Replaces C=O by C-H and C-N
1-Nu of NH3 on carbonyl group forming IMINE
2-Oxygen leaves
3-Nitrogen is deprotonated

32
Q

What does the Hoffman elimination do?

A

Converts an amine into a quaternary ammonium salt prior to beta elimination
1-make good LG (quat. Ammonium salt)
2-Use strong base to cause anti-periplanar E2 elimination

33
Q

Is the more substituted or less substituted pi bond formed in the Hoffman reaction and why?

A

LESS.

The sterics of the bulky N(CH3)3 prevent abstraction of the more hindered hydrogen

Chem 352 (3 decks)

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