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Last updated 11:23 AM on 6/12/26

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15 Terms

1

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Amide Synthesis - Nucleophilic Acyl Substitution (Acid chloride) - Reversible

(Acid → Amine)

Reagants: Amine with r group, base (Pr), H3o+

Nucleophilic attack
Tetrahedral Intermediate
Proton transfer (O- → OH) (NH2-R) → (NH-R) → Applicable if good leaving group isn’t there.
Turn OH into leaving group using hydronium (Iminum ion forms) → Applicable if good leaving group isn’t there.
Base (Et3N) attacks and takes away H
Amide forms (+H2O)

<p>(Acid → Amine)</p><p>Reagants: Amine with r group, base (Pr), H3o+</p><p></p><ol><li><p>Nucleophilic attack</p></li><li><p>Tetrahedral Intermediate</p></li><li><p>Proton transfer (O- → OH) (NH2-R) → (NH-R) → <strong>Applicable if good leaving group isn’t there.</strong></p></li><li><p>Turn OH into leaving group using hydronium (Iminum ion forms) → <strong>Applicable if good leaving group isn’t there.</strong></p></li><li><p>Base (Et3N) attacks and takes away H</p></li><li><p>Amide forms (+H2O)</p></li></ol><p></p>

2

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<p>Gringard Reaction - Nucleophilic Acyl Addition (Aldehyde → Secondary, Ketone → Tertiary, Ester → Tertiary)</p>

Gringard Reaction - Nucleophilic Acyl Addition (Aldehyde → Secondary, Ketone → Tertiary, Ester → Tertiary)

Nucleophilic attack
Tetahedral Intermediate
Protonate (using hydronium)
Final product

For ester, repeat the process.

Two R groups should be present. (tertiary alcohol)

<ol><li><p>Nucleophilic attack</p></li><li><p>Tetahedral Intermediate</p></li><li><p>Protonate (using hydronium)</p></li><li><p>Final product</p></li></ol><p></p><p>For ester, repeat the process.</p><p></p><ul><li><p>Two R groups should be present. (tertiary alcohol)</p></li></ul><p></p>

3

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<p>Nucleophilic Acyl Addition (Cynanohydrin) Ketone → Tertiary Alcohol Reagants: H3O+, Nacn</p>

Nucleophilic Acyl Addition (Cynanohydrin) Ketone → Tertiary Alcohol Reagants: H3O+, Nacn

Nucleophilic attack (CN comes in)

Protonation or charged tetrahedral intermediate

Formation of product (H2O also?)

<p></p><p></p><p></p><p></p><ol><li><p>Nucleophilic attack (CN comes in)</p></li></ol><p></p><ol start="2"><li><p>Protonation or charged tetrahedral intermediate</p></li></ol><p></p><ol start="3"><li><p>Formation of product (H2O also?)</p></li></ol><p></p><p></p><p></p>

4

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<p>Formation of amines to imines (Acidic conditions)</p><p></p>

Formation of amines to imines (Acidic conditions)

Nucleophilic attack

Formation of tetrahedral intermediate

Proton transfer (NH2 → NH , O → OH)

Leaving group is good

Leaving group leaves, double bond in N forms

Imminium ion

Lose a proton (from NH)

Note: The reaction of secondary amines give enamines

<ol><li><p>Nucleophilic attack</p></li></ol><p></p><ol start="2"><li><p>Formation of tetrahedral intermediate</p></li></ol><p></p><ol start="3"><li><p>Proton transfer (NH2 → NH , O → OH)</p></li></ol><p></p><ol start="4"><li><p>Leaving group is good</p></li></ol><p></p><ol start="5"><li><p>Leaving group leaves, double bond in N forms</p></li></ol><p></p><ol start="6"><li><p>Imminium ion</p></li></ol><p></p><ol start="7"><li><p>Lose a proton (from NH)</p></li></ol><p></p><p></p><p>Note: The reaction of secondary amines give enamines</p><p></p><p></p>

5

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<p>Fischer Esterification (Carboxylic acid → Ester ) :Nucleophlic acyl substitution </p>

Fischer Esterification (Carboxylic acid → Ester ) :Nucleophlic acyl substitution

Aldol reaction (Add H+)

Nucleophilic attack

Tetrahedral intermediate

Deprotonate the r group

Cause leaving group through hydronoim

Deprotonate to remove central hydrogen

<ol><li><p>Aldol reaction (Add H+)</p></li></ol><p></p><ol start="2"><li><p>Nucleophilic attack </p></li></ol><p></p><ol start="3"><li><p>Tetrahedral intermediate</p></li></ol><p></p><ol start="4"><li><p>Deprotonate the r group</p></li></ol><p></p><ol start="5"><li><p>Cause leaving group through hydronoim</p></li></ol><p></p><ol start="6"><li><p>Deprotonate to remove central hydrogen</p></li></ol><p></p><p></p><p></p>

6

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Jones Oxidation

Primary alcohol → Carboxylic acid (Skips aldehyde)

Secondary alcohol → Ketone

7

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Swern Oxidation (DMSO, base, electrophile)

Primary alcohol → Aldehyde

Secondary alcohol → Ketone

Byproducts: Me2S, Co, Co2, HCl

8

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<p>Acetal Formation (Secondary Alcohol → Acetal) </p><p></p>

Acetal Formation (Secondary Alcohol → Acetal)

Aldol
Nucleophilic attack
Deprotonation (using OH2) Now EtO
Leaving group (OH2+) using hydronium
Eto into double bond (Oxinium intermediate)
Nucleophilic attack
Intermediate
DeProtonate
Acetal formed! +H2O

<ol><li><p>Aldol</p></li><li><p>Nucleophilic attack</p></li><li><p>Deprotonation (using OH2) Now EtO</p></li><li><p>Leaving group (OH2+) using hydronium</p></li><li><p>Eto into double bond (Oxinium intermediate)</p></li><li><p>Nucleophilic attack</p></li><li><p>Intermediate</p></li><li><p>DeProtonate</p></li><li><p>Acetal formed! +H2O</p></li></ol><p></p>

9

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Rosenmund reduction

Reduce C-Cl (acid chloride) to C-H bond (uses Pd/BaSo4)

<p>Reduce C-Cl (acid chloride) to C-H bond (uses Pd/BaSo4)</p><p></p>

10

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NaBh4 reduction (mechanism)

Reduction of aldehydes and ketones to alcohols

Will not reduce esters, carboxylic acid and amides

<ul><li><p>Reduction of aldehydes and ketones to alcohols</p></li></ul><p></p><ul><li><p>Will not reduce esters, carboxylic acid and amides</p></li></ul><p></p><p></p><p></p><p></p>

11

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Reduction of LiBh4

Reduction of aldehydes and ketones to alcohols

WILL reduce esters as well

<ul><li><p>Reduction of aldehydes and ketones to alcohols </p></li></ul><p></p><ul><li><p>WILL reduce esters as well</p></li></ul><p></p><p></p><p></p>

12

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LiAlH4 reduction

Reduction of amides to aldehydes amines

Reduction to carboxylic acid to alcohol

13

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DiBAL-H (eduction) with -78 degrees

Reduction of esters to aldehydes

Reduction of nitriles to aldehydes (−C≡N)

Lactones (cyclic ester) to lactols (hemiacetal)

<ul><li><p>Reduction of esters to aldehydes</p></li></ul><p></p><ul><li><p>Reduction of nitriles to aldehydes (<strong><em>−C≡N)</em></strong></p></li></ul><p></p><ul><li><p>Lactones (cyclic ester) to lactols (hemiacetal)</p></li></ul><p></p><p></p><p></p><p></p><p></p><p></p>

14

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Reduction of borane

Reduction of amides and carboxylic acids

15

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Reduction using odium cyanoborohydride and sodium triacetoxy borohydride

Ammonium ion reduce to amines

<p>Ammonium ion reduce to amines</p><p></p><p></p><p></p>