T3 Reactions Spivak Flashcards by Brandon Champagne

Q

Carboxylic acid –> Ester

A

2HCl and ROH

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Q

Transesterification

A

A) Base ether (NaH WES -OR’)

B) 2HCl and R’OH

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Q

Ester –> Amide

A

NHR2 (amine) and B-

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Q

Amide –> Carboxylic Acid

A

A) Base (OH- with anion product)

B) 2HCl and water

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Q

Acid Chloride –> Carboxylic Acid

A

Water, TEA

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Q

Carboxylic Acid –> Acid Chloride

A

SOCl2

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Q

Acid Chloride –> Ester

A

ROH and TEA

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Q

Acid Chloride –> Amide

A

HNR2 and TEA

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Q

Ester –> Carboxylic Acid (anion)

A

Use OH- base (also deprotonates product)

2. Use 2HCl and a water

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Q

Acid Chloride –> Anhydride

A

NaH, Carboxylic Acid -(R’)

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Q

Anhydride –> Ester (+CA)

A

ROH (H+ transfer)

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Q

Carboxylic Acid –> Anhydride

A

NaH

Acid Chloride

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Q

Anhydrides –> Amide

A

(2) H2NR

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Q

Carboxylic acid –> Amide

A

DCC

Amine

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Q

Carboxylic Acid –> Ester (better way)

A

DCC / DMAP

ROH

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Q

Acid Chloride –> Isocyanate

Curtis rearr.

A

NaN3

Q

Isocyanate –> Amine

A

2 H2O

Q

Isocyanate –> Carbamate (Urethane)

A

ROH

Q

Isocyanate –> Urea

A

R2NH

Q

Phosgene –> Urea

A

2 HNR2

2 TEA

Q

Phosgene –> Carbonate

A

2 ROH

2 TEA

Q

Phosgene –> Carbamate

A

1 ROH
1 HNR2
2 TEA

Q

Acid Chloride –> Alcohol

A

LiAlH4

H2O

Q

Ester/Anhydride –> Alcohol

A

LiAlH4

H2O

Q

Acid Chloride –> Aldehyde

A

DA MONSTA

Water

Q

Ester –> Aldehyde

A

DIBAL (Diisobutylaluminum hydride)

Water

Q

Acid Chloride/ Esters –> 3° Alcohol

A

Grignard and water work up

Q

Acid Chloride –> Ketone

A

Cuprate (CuR2Li) and water work up

Q

Amide –> Amine

A

LiAlH4

H2O

Q

Carboxylic acid –> Alkyl halide

Hunsdieker

A

Ag2O

Br2

Q

Alkyl bromide –> CA

A

CO2
Mg
Water work up

Q

Nitriles –> Alkylhalides

A

NaCN

Q

Nitriles –> CA

A

H3O+

H2O