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Orgo 2 > Nucleophilic Acyl Substitution > Flashcards

Nucleophilic Acyl Substitution Flashcards

1
Q

Carboxylic acid to acyl chloride

A

SOCl2

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1
Q

Acyl chloride to carboxylic acid

A

H2O

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2
Q

Acyl chloride to aldehyde

A

DIBAL-H, -78 C or LiAl(OR)3H

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3
Q

Acyl chloride to amide

A

NH3 (excess)

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4
Q

Acyl chloride to ester

A

HOR, pyridine

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5
Q

Acyl chloride to anhydride

A

HOAc, pyridine

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6
Q

Anhydride to carboxylic acid

A

H2O

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7
Q

Anhydride to ester

A

HOR, pyridine

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8
Q

Ester to carboxylic acid

A

H3O+, H2O

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9
Q

Ester to Aldehyde

A

DIBAL-H, -78 C or LiAl(OR)3H

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10
Q

Ester to amide

A

NH3

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11
Q

Amide to carboxylic acid

A

H3O+, H2O, heat

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12
Q

Carboxylic acid to ester

A

H3O+, HOR

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13
Q

RX to RCO2H (carboxylic acid)

A
  1. Mg, RO
  2. CO2
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14
Q

Carboxylic acid to primary alcohol

A
  1. LiAlH4
  2. H2O
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15
Q

Selective reduction of carboxylic acids to primary alcohol

A

BH3THF (Won’t touch ketone/aldehyde)

16
Q

General SnAc (Nucleophilic acyl substitution)

A
  1. Adn, Lone pair of nucleophile attacks carbon of carbonyl, pushes lone pair up onto oxygen
  2. Eb, lone pair of oxygen makes double bond, leaving group departs
17
Q

Acid catalysis of SnAc

A

1) Pt, lone pair on O takes H from H3O+
2) AdN, OH2 attacks carbonyl carbon, pushes lone pair onto oxygen
3) Pt, OH2 takes H from OH2 that just attached
4) Pt, Leaving group takes H from H3O+
5) Eb, lone pair from OH makes double bond, leaving group departs
6) Pt, OH2 takes H from OH

18
Q

SnAc under basic conditions

A

1) Adn, OH attacks carbonyl carbon, pushes lone pair onto oxygen
2) Eb, lone pair on oxygen makes double bond, expels leaving group
3) Pt, Leaving group takes H from OH

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