Chapter 20 Reactions

0.0(0)

Studied by 0 people

Call Kai

Learn

Practice Test

Spaced Repetition

Match

Flashcards

Knowt Play

Card Sorting

1/38

There's no tags or description

Looks like no tags are added yet.

39 Terms

1

New cards

CrO₃ or another strong Cr oxidant (H2CrO4 or K2Cr2O7)

1° alcohol → carboxylic acid

<p>1° alcohol → carboxylic acid</p>

2

New cards

Grignard carboxylation

Grignard → carboxylic acid; adds one carbon

<p>Grignard → carboxylic acid; adds one carbon</p>

3

New cards

<p>Grignard carboxylation Mechanism</p>

Grignard carboxylation Mechanism

knowt flashcard image

4

New cards

Carboxylic acid reduction: Lithium Aluminum Hydride

1° alcohol

Could even be: 1. LiAlH₄ 2. H₃O⁺

<p>1° alcohol</p><p><strong>Could even be:</strong> 1. LiAlH₄ 2. H₃O⁺</p>

5

New cards

Selective Reduction of Carboxylic Acid to Primary Alcohols

Selectively reduces carboxylic acid → 1° alcohol

<p>Selectively reduces carboxylic acid → 1° alcohol</p>

6

New cards

Fischer esterification

Carboxylic acid → ester (Reversible)

<p>Carboxylic acid → ester (Reversible)</p>

7

New cards

<p>Fischer Esterification (Mechanism)</p>

Fischer Esterification (Mechanism)

knowt flashcard image

8

New cards

<p><strong>Reactions of Carboxylic Acids: </strong>Acid chloride formation</p>

Reactions of Carboxylic Acids: Acid chloride formation

Carboxylic acid → acid chloride

<p>Carboxylic acid → acid chloride</p>

9

New cards

Hydrolysis of Acid Chlorides (how they go back to a carboxylic acid)

Acid chloride → carboxylic acid

<p>Acid chloride → carboxylic acid</p>

10

New cards

<p>Hydrolysis of Acid Chlorides (Mechanism)</p>

Hydrolysis of Acid Chlorides (Mechanism)

knowt flashcard image

11

New cards

Making Anhydrides from Acid Chlorides

(RCOO⁻)

Acid chloride → anhydride

<p>(RCOO⁻)</p><p>Acid chloride → anhydride</p>

12

New cards

Making Esters from Acid Chlorides

Acid chloride → ester

<p>Acid chloride → ester</p>

13

New cards

<p>Making Esters from Acid Chlorides (Mechanism)</p>

Making Esters from Acid Chlorides (Mechanism)

knowt flashcard image

14

New cards

<p>Making Amides from Acid Chlorides</p>

Making Amides from Acid Chlorides

Acid chloride → amide

<p>Acid chloride → amide</p>

15

New cards

<p>Making Amides from Acid Chlorides (Mechanism 1° amine)</p>

Making Amides from Acid Chlorides (Mechanism 1° amine)

knowt flashcard image

16

New cards

Make Ketones from Gilman Reagent (R₂CuLi)

Acid chloride → ketone

<p>Acid chloride → ketone</p>

17

New cards

Reduction of Acid Chlorides to Primary Alcohols

Acid chloride → 1° alcohol

<p>Acid chloride → 1° alcohol</p>

18

New cards

Reduction of Acid Chlorides to Aldehydes

Acid chloride → aldehyde

<p>Acid chloride → aldehyde</p>

19

New cards

Hydrolysis of Anhydrides

Anhydride → two carboxylic acids

<p>Anhydride → two carboxylic acids</p>

20

New cards

<p>Hydrolysis of Anhydrides (Mechanism)</p>

Hydrolysis of Anhydrides (Mechanism)

knowt flashcard image

21

New cards

Making Esters from Anhydrides

Anhydride → ester + carboxylic acid

If the anhydride is asymmetrical, a mixture of products is formed

<p>Anhydride → ester + carboxylic acid</p><p>If the anhydride is asymmetrical, a mixture of products is formed</p>

22

New cards

Making Amides from Anhydrides

Anhydride → amide + carboxylate/ammonium salt

2 equivalents NH₃, 1° or 2° amine

This method is only useful if the anhydride is symmetrical.

<p>Anhydride → amide + carboxylate/ammonium salt</p><p>2 equivalents NH₃, 1° or 2° amine</p><p>This method is only useful if the anhydride is symmetrical.</p>

23

New cards

Reduction of Anhydrides: Lithium aluminum hydride

Anhydride → two 1° alcohols

<p>Anhydride → two 1° alcohols</p>

24

New cards

Saponification (basic ester hydrolysis)

Ester → carboxylate + alcohol

<p>Ester → carboxylate + alcohol</p>

25

New cards

<p>Saponification (basic ester hydrolysis) (Mechanism)</p>

Saponification (basic ester hydrolysis) (Mechanism)

knowt flashcard image

26

New cards

Acid-catalyzed ester hydrolysis

Ester → carboxylic acid + alcohol

<p>Ester → carboxylic acid + alcohol</p>

27

New cards

<p>Acid-catalyzed ester hydrolysis (Mechanism)</p>

Acid-catalyzed ester hydrolysis (Mechanism)

knowt flashcard image

28

New cards

Making Amides from Esters

NH₃, 1° or 2° amine, heat/excess

Ester → amide

<p>NH₃, 1° or 2° amine, heat/excess</p><p>Ester → amide</p>

29

New cards

<p>Making Amides from Esters (Mechanism)</p>

Making Amides from Esters (Mechanism)

knowt flashcard image

30

New cards

Making Tertiary Alcohols from Grignards/Organolithiums

Ester → 3° alcohol

Esters react with moles of Grignard or organolithium compounds to form tertiary alcohols, so yes it adds twice

<p>Ester → 3° alcohol</p><p>Esters react with moles of Grignard or organolithium compounds to form tertiary alcohols, so yes it adds twice</p>

31

New cards

Reduction of Esters to Primary Alcohols: Lithium Aluminum Hydride

Ester → 1° alcohols

<p>Ester → 1° alcohols</p>

32

New cards

Reduction of Esters to Aldehydes

Ester → aldehyde + alcohol

<p>Ester → aldehyde + alcohol</p>

33

New cards

Acid-catalyzed amide hydrolysis

Amide → carboxylic acid + ammonium/amine-derived product

<p>Amide → carboxylic acid + ammonium/amine-derived product</p>

34

New cards

<p>Acid-catalyzed amide hydrolysis (Mechanism)</p>

Acid-catalyzed amide hydrolysis (Mechanism)

knowt flashcard image

35

New cards

Base Hydrolysis of Amides

Amide → carboxylate anion + amine/ammonia

<p>Amide → carboxylate anion + amine/ammonia</p>

36

New cards

<p>Base Hydrolysis of Amides (Mechanism)</p>

Base Hydrolysis of Amides (Mechanism)

knowt flashcard image

37

New cards

<p>Reduction of Amides to Amines Practice</p>

Reduction of Amides to Amines Practice

Amide → amine

<p>Amide → amine</p>

38

New cards

Nitrile hydrolysis

Nitrile → carboxylic acid/carboxylate through an amide

<p>Nitrile → carboxylic acid/carboxylate through an amide</p>

39

New cards

Reduction of Nitriles to Primary Amines

Nitrile → 1° amine

<p>Nitrile → 1° amine</p>