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Organic Chem > Carboxylic acids > Flashcards

Carboxylic acids Flashcards

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1
Q

Preparation of Carboxylic acids

A
  1. Oxidation of primary alcohols or aldehydes
  2. Hydrolysis of nitriles
  3. Hydrolysis of ester
  4. Iodoform reaction of methyl ketone or ethanal
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2
Q

Oxidation of primary alcohols or aldehydes

A

Reagents: acidified potassium dichromate
Condition: heat under reflux
Observation: orange to green

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3
Q

Hydrolysis of nitriles

A

Condition: acid or alkaline conditions, heat under reflux

nitrile + H+ –> carboxylic acid + NH4+
nitrile + OH- –> carboxylate anion + NH3
carboxylate anion + H+ (excess strong acid) –> carboxylic acid

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4
Q

Hydrolysis of ester

A

Condition: acid or alkaline conditions, heat under reflux

ester + H+ –> carboxylic acid + alcohol
ester + OH- –> carboxylic acid anion + alcohol
carboxylic acid anion + H+ (excess strong acid) –> carboxylic acid

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5
Q

Iodoform reaction of methyl ketone or ethanal

A

Reagents: iodine and NaOH or KI and NaClO then excess strong acid
Condition: warm gently

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6
Q

With LiAlH4

A

Type of reaction: reduction
Conditions: in dry ether then acid workup
Change in functional group: carboxylic acid –> primary alcohol

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7
Q

With bases

A

Type of reaction: acid-base reaction
metal hydroxide + acid –> salt + water
metal oxide + acid –> salt + water
metal carbonate + acid –> salt + CO2 + water
ammonia + acid –> ammonium salt

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8
Q

With PCl5 or SOCl2

A

Type of reaction: addition-elimination
Condition: anhydrous
Change in functional group: carboxylic acid –> acyl chloride

carboxylic acid + PCl5 –> acyl chloride + POCl3 + HCl
carboxylic acid + SOCl2 –> acyl chloride + SO2 + HCl

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9
Q

With alcohols

A

Type of reaction: esterification
Condition: heat under reflux, sulfuric acid catalyst

carboxylic acid + alcohol ⇌ ester + water

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10
Q

With chlorine

A

Type of reaction: free radical substitution
Conditions: UV light
Change in functional group: carboxylic acid –> chlorocarboxylic acid

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Organic Chem (18 decks)

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