Reactions Chapter 12

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26 Terms

1

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<p>What is formed with:</p><p>Formaldehyde + Grignard + H<sub>3</sub>O<sup>+</sup></p>

What is formed with:

Formaldehyde + Grignard + H₃O⁺

Primary alcohol

<p>Primary alcohol</p>

2

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<p>What is formed with:</p><p>Aldehyde (other than formaldeyde) + Grignard + H<sub>3</sub>O<sup>+</sup></p>

What is formed with:

Aldehyde (other than formaldeyde) + Grignard + H₃O⁺

Secondary alcohol

<p>Secondary alcohol</p>

3

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<p>What is formed with:</p><p>Ketone + Grignard + H<sub>3</sub>O<sup>+</sup></p>

What is formed with:

Ketone + Grignard + H₃O⁺

Tertiary alcohol

<p>Tertiary alcohol</p>

4

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<p>What is formed with:</p><p>CO<sub>2</sub> + Grignard</p>

What is formed with:

CO₂ + Grignard

Carboxylic acid

<p>Carboxylic acid</p>

5

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<p>What is formed with:</p><p>Ester + Grignard</p><p><em>and special note?</em></p>

What is formed with:

Ester + Grignard

and special note?

Tertiary alcohol

Has two of the same R groups!

<p>Tertiary alcohol</p><p>Has two of the same R groups!</p>

6

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<p>What is formed with:</p><p>Acyl chloride + Grignard</p><p><em>and special note?</em></p>

What is formed with:

Acyl chloride + Grignard

and special note?

Tertiary alcohol

Has two of the same R groups!

<p>Tertiary alcohol</p><p>Has two of the same R groups!</p>

7

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<p>What is formed with:</p><p>Aldehyde/ketone + cyanide ion</p>

What is formed with:

Aldehyde/ketone + cyanide ion

Cyanohydrin

<p>Cyanohydrin</p>

8

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<p>Reactions of cyanohydrins:</p>

Reactions of cyanohydrins:

Can be used to make α-hydroxycarboxylic acid or reduced to a primary amine with an OH group on the β carbon

<p>Can be used to make α-hydroxycarboxylic acid or reduced to a primary amine with an OH group on the β carbon</p>

9

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<p>What is formed with:</p><p>Aldehyde + hydride ion (BH4)</p>

What is formed with:

Aldehyde + hydride ion (BH4)

Primary alcohol

<p>Primary alcohol</p>

10

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<p>What is formed with:</p><p>Ketone + hydride ion (BH4) + H<sub>3</sub>O<sup>+ </sup></p>

What is formed with:

Ketone + hydride ion (BH4) + H₃O⁺

Secondary alcohol

<p>Secondary alcohol</p>

11

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<p>What is formed with:</p><p>Acyl chloride + hydride ion (BH4) + H<sub>3</sub>O<sup>+</sup></p>

What is formed with:

Acyl chloride + hydride ion (BH4) + H₃O⁺

Primary alcohol

<p>Primary alcohol</p>

12

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<p>What is formed with:</p><p>Ester + hydride ion (LiAlH4) + H<sub>3</sub>O<sup>+</sup></p>

What is formed with:

Ester + hydride ion (LiAlH4) + H₃O⁺

2 primary alcohols

<p>2 primary alcohols</p>

13

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<p>What is formed with:</p><p>Carboxylic acid + hydride ion (LiAlH4) + H<sub>3</sub>O<sup>+</sup></p>

What is formed with:

Carboxylic acid + hydride ion (LiAlH4) + H₃O⁺

Primary alcohol

(same # of C as the carboxylic acid)

<p>Primary alcohol</p><p>(same # of C as the carboxylic acid)</p>

14

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<p>What is formed from:</p><p>Amide + hydride ion (LiAlH<sub>4</sub>) + H<sub>2</sub>O</p><p><em>and special note?</em></p>

What is formed from:

Amide + hydride ion (LiAlH₄) + H₂O

and special note?

Primary, secondary, or tertiary amine (depends)

H2O is used instead of H₃O⁺

<p>Primary, secondary, or tertiary amine (depends)</p><p>H2O is used instead of H<sub>3</sub>O<sup>+</sup></p>

15

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<p>What is formed with:</p><p>Aldehyde/ketone + amine + trace acid</p>

What is formed with:

Aldehyde/ketone + amine + trace acid

Imine

<p>Imine</p>

16

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<p>What is formed with:</p><p>Imine + H<sub>2</sub>O + trace acid</p>

What is formed with:

Imine + H₂O + trace acid

Aldehyde/ketone + protonated amine

<p>Aldehyde/ketone + protonated amine</p>

17

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<p>What is formed with:</p><p>Aldehyde/ketone + ammonia + trace HCl + H<sub>2</sub> + Pd/C</p>

What is formed with:

Aldehyde/ketone + ammonia + trace HCl + H₂ + Pd/C

Amine

(reductive amination)

<p>Amine</p><p>(reductive amination)</p>

18

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<p>What is formed with:</p><p>Aldehyde/ketone + alcohol + HCl</p>

What is formed with:

Aldehyde/ketone + alcohol + HCl

Acetal

(reactions of aldehydes and ketones w/ alcohol)

<p>Acetal</p><p>(reactions of aldehydes and ketones w/ alcohol)</p>

19

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<p>What is formed with:</p><p>Acetal + H<sub>2</sub>O + HCl</p>

What is formed with:

Acetal + H₂O + HCl

Aldehyde/ketone + alcohol

(reverse reaction, reactions of aldehydes and ketones w/ alcohol)

<p>Aldehyde/ketone + alcohol</p><p>(reverse reaction, reactions of aldehydes and ketones w/ alcohol)</p>

20

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<p>What is formed with:</p><p>α,β-unsaturated aldehyde/ketone + STRONG nucleophile + H<sub>2</sub>O</p><p>(can have 1) NaBr4 then 2) EtOH</p>

What is formed with:

α,β-unsaturated aldehyde/ketone + STRONG nucleophile + H₂O

(can have 1) NaBr4 then 2) EtOH

1,2 direct addition

<p>1,2 direct addition</p>

21

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<p>What is formed with:</p><p>α,β-unsaturated aldehyde/ketone + WEAK nucleophile + H<sub>2</sub>O</p>

What is formed with:

α,β-unsaturated aldehyde/ketone + WEAK nucleophile + H₂O

1,4 conjugate addition

<p>1,4 conjugate addition</p>

22

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<p>What is formed with:</p><p>REACTIVE α,β-unsaturated carboxylic acid derivative + nucleophile</p>

What is formed with:

REACTIVE α,β-unsaturated carboxylic acid derivative + nucleophile

Nucleophilic addition-elimination products

reactive: acyl chlorides

<p>Nucleophilic addition-elimination products</p><p>reactive: acyl chlorides</p>

23

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<p>What is formed with:</p><p>LESS REACTIVE α,β-unsaturated carboxylic acid derivative + nucleophile</p>

What is formed with:

LESS REACTIVE α,β-unsaturated carboxylic acid derivative + nucleophile

1,4 conjugate addition

less reactive: esters and amides

<p>1,4 conjugate addition</p><p>less reactive: esters and amides</p>

24

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Carboxylic acid derivatives undergo…

Nucleophilic acyl substitution (Y^- can leave)

25

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Aldehydes + ketones undergo…

Nucleophilic addition (neither alkyl nor hydride groups can leave)

26

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<p>What is formed with:</p><p>Alkyl halide + Mg + Et<sub>2</sub>O (diethyl ether)</p>

What is formed with:

Alkyl halide + Mg + Et₂O (diethyl ether)

Grignard reagent

<p>Grignard reagent</p>