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Carboxylic Acids and Derivatives: Properties, Nomenclature, and Synthesis - Prof. Roman E., Study notes of Biology

An overview of carboxylic acids, their nomenclature, synthesis, and properties. It covers the addition of the -oh group to the carbonyl group to produce the carboxyl group, the different types of carboxylic acids, their nomenclature rules, and methods of synthesis. Additionally, it discusses the solubility, ionization, and neutralization of carboxylic acids, as well as the formation of carboxylate ions and salts. The document also introduces esters, amines, and amides, and their respective nomenclature and reactions.

Typology: Study notes

Pre 2010

Uploaded on 08/10/2009

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Carboxylic Acids
1. -OH group added to carbonyl group
produces carboxyl group
2. May be attached to alkyl or aromatic
ethanoic acid methanoic acid
(acetic acid) (formic acid)
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Carboxylic Acids

  1. -OH group added to carbonyl group produces carboxyl group
  2. May be attached to alkyl or aromatic

ethanoic acid methanoic acid (acetic acid) (formic acid)

Carboxylic Acid Nomenclature

  1. Longest C chain with carboxyl group is parent chain
  2. Replace -e in parent name with -oic acid
  3. Carboxyl C is C
  4. Number & name side groups appropriately

Carboxylic Acids Synthesis

  1. Oxidation of aldehyde produces carboxylic acid
  2. Complete oxidation of alcohol produces aldehyde, then carboxylic acid

ethanol ethanal ethanoic acid (acetaldehyde) (acetic acid)

Carboxylic Acid Properties

1. Solubility

  1. Ionization
  2. Neutralization

Carboxylic Acid Ionization

1. Donate H+^ to H 2 O to form H 3 O+

2. Weak acids, but > phenols

3. Negative ion is referred to as

carboxylate ion

Carboxylate Ion Example

1. Donate H+^ to H 2 O to form H 3 O+

2. Weak acids, but > phenols

3. Negative ion is referred to as

carboxylate ion

ethanoic acid ethanoate ion (acetic acid) (acetate ion)

Neutralization

methanoic sodium methanoate acid (sodium formate)

benzoic acid sodium benzoate

Organic Salts

copper ( I ) naphthalate

benzyl ammonium chloride

Esterification

ethanoic methanol methyl ethanoate acid

Ester Nomenclature

  1. Name alkyl group from alcohol, then carboxylic acid
  2. Change -ic to -ate

methyl ethanoate ethyl methanoate (methyl acetate) (ethyl formate)

Acid hydrolysis

  1. Produces carboxylic acid and alcohol

methyl benzoic methanol benzoate acid

Base hydrolysis

  1. Saponification- produces salt of carboxylic acid (soap) & alcohol

methyl sodium methanol propanoate propanoate

1 o, 2o, 3o^ amines

1 o^ amine 2 o^ amine

3 o^ amine

Amine Nomenclature

  1. Longest/largest carbon chain/ring is parent , N-C is C
  2. Remaining alkyl or aromatic groups attached to N, named as N- substituents
  3. If identical, use di- & tri-
  4. If different, arrange alphabetically