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Organic chemistry > Carboxylic acids > Flashcards

Carboxylic acids Flashcards

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1
Q

Characteristics ?

A

Acids + Carboxyl group
R-COOH
Weak in Water
Boiling points rise with increase about 18 ° per Methylene group
Greater solubility –> Ab C7 Insoluble
The carboxylic acids with up to four carbon atoms will mix with water in any proportion

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2
Q

Carboxyl group

A

Carbonyl + OH

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3
Q

Dissociation

A

Displaced to left

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4
Q

Dimers

A

Double molecules associated by H Bonds

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5
Q

Reactions

A
  1. Salt formation –> Neutralization with Bases
  2. Acyl Halides –> -OH replaced by Halogen
  3. Amide –> Carboxylic acid –> Ammonium Salt —> Heat–> Amide
  4. Anhydrides –> -H2O
  5. Esters –> with Alks
  6. Nitriles –> With Ammonia
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6
Q

Compounds (21)

A 
Formic acid
Acetic acid 
Propionic/ Butyric/ Isobutyric acid 
Lactic acid
Pyruvic acid 
Beta-Hydroxybutyric/ Acetoacetic/ Acetone 
Oxalic acid 
Citric acid
Tartaric acid 
EDTA
Benzoic acid
Salicylic acid
Suflosalicylic 
Aspririn 
PAB
PAS
Gallic acid 
Mandelic acid 
Homogentisic acid
Pthalic acids 
Phenolphtalein
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7
Q

Formic acid

A

Stings of bees and wasps+ Nettles
Painful blisters
Mild reducing agent (-CH=O)
Strongest simple organic acid

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8
Q

How is Formic acid made?

A

It is made by the action of sulfuric acid upon sodium formate,
which is produced from carbon monoxide and sodium hydroxide

!!failure to form an anhydride!!

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9
Q

Acetic Acid

A
  • Vinegar: A dilute solution of acetic acid produced by fermentation and oxidation of natural carbohydrates
  • Acetate: a salt, ester, or acylal of acetic acid
  • Biologically, an important metabolic intermediate, and it occurs naturally in body fluids and in plant juices
  • Pure acetic acid, often called glacial acetic acid, is a corrosive, colourless liquid (boiling point 117.9 °C) ; melting point 16.6 that is completely miscible with water
  • Acetyl deriveratives –> Intermediary metabolites

Methanol + CarbonMonoxide –> Acetic acid

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10
Q

Aluminium acetate

A

Local applications

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11
Q

Trichloroacetic acid

A

Deproteinization of Blood samples

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12
Q

Propionic/ Butyric/ Isobutyric acid

A

Unpleasant smell, But ester have a nice smell (Fresh Butter)
Butyric –> Fatty acid

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13
Q

Fatty acids

A
  • Important component of lipids
  • Consists of a straight chain of an even number of carbon atoms, with hydrogen atoms along the length of the chain and at one end of the chain and a carboxyl group (−COOH) at the other end
  • Unsaturated –> More reactive
  • Commonly they exist in combination with glycerol (an alcohol) in the form of triglyceride
  • Soaps are the sodium and potassium salts of fatty acids
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14
Q

Lipids

A

fat-soluble components of living cells

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15
Q

Oxalic acid

A

Ethanedioic acid

Its Potassium salts in Vegetables –> Crystalls of calcium oxalate in Urine –> also PRESERVING BLOOD SAMPLES

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16
Q

Valeric / Isovaleric acid

A

weak sedative properties
in Valeriana officinalis
Isovaleric –> sexual attractant for some animals (Cats)

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17
Q

Biologically important derivatives ?

A

Contain mainly Hydroxyl / Keto / Amino groups

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18
Q

Lactic acid

A

Formed when milk turns sour –> Lactobacillus

Brine of Sauerkraut/ Siloed Fodder

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19
Q

Lactic acid in Medicine?

A

Contracting Muscles

Calcium Substitution Therapy -> Calcium Lactate

20
Q

How is Pyruvic acid produced?

A

Produced by distillation of Tartaric acid

21
Q

Pyruvic acid

A

Important intermediate in carbohydrate metabolism

22
Q

How is Lactic acid produced ?

A

Reduction of Pyruvic acid

23
Q

What are the Ketone Bodies?

A
  • Three water-soluble molecules –>
  • Beta Hydroxy butyric acid/ Acetoacetic acid / Acetone
  • Produced by the liver from fatty acids during periods of low food intake , carbohydrate restrictive diets, starvation, prolonged intense exercise or in untreated type 1 diabetes mellitus
  • These ketone bodies are readily picked up by the extra-hepatic tissues, and converted into acetyl-CoA which then enters the citric acid cycle and is oxidized in the mitochondria for energy
24
Q

Precursor of Acetoacetic acid ?

A

HMG

–> Beta-Hydroxy-Beta-Methylglutaric acid

25
Q

HMG

A

Key intermediate in biosynthesis of steroid compounds

26
Q

Citric acid

A

Citrus fruits
Acidulant in foods and soft drinks
Able to form complexes with metal ions

27
Q

Commercial manufacture of citric acid

A

mainly by fermentation of molasses or starch with aspergillus niger

28
Q

Tartaric acids

A

Dihydroxysuccinic acids
Contain 2 asymmetric carbons
–> D(+) / L (-) / Meso Form
Constituents of complex forming reagents with metal ions –> Fehlings

29
Q

EDTA

A

Potent chelating agent

Forms strong complexes (1:1) with alkaline heart and heavy metal ions

30
Q

EDTA in Medicine

A

Antidotes in heavy metal intoxication

31
Q

Aromatic carboxylic acids

A 
Benzoic acid 
Salicylic acid 
Gallic acid 
Phtalic acid 
Hippuric acid
Sulfosaliylic acid
32
Q

Benzoic acid

A

white crystalline solid
Little soluble in cold water
Inhibits growth of microorganisms at low PH

33
Q

Sodium Benzoate

A

Food preservative

34
Q

What happens if Benzoic acid is ingested?

A

Detoxified by combination with Glycine and eliminated in urine as HIPPURIC ACID

35
Q

Salicylic acid

A

Conserving Food
Antipyretic –> Lower Fever
Analgesic action –> Pain reducing
Aspirin !

36
Q

How is Aspirin produced?

A

Acetyl derivative of Salicylic acid (by Hydroliysis)

37
Q

What happens if you ingest Aspirin?

A

Passes through stomach unchanged –> Hydrolyzed to Salicyclic acid in the intestine ( Alkaline reaction)

38
Q

PAS

A

p-Aminosalicylic acid
Treatment of tuberculosis
Disadvantage: Binding of Iodine

39
Q

Sulfosalicylic acid

A

Contains strongly acidic sulfate group
Presence of Proteins –> White Precipitate
—> Proteine Urine Test

40
Q

PAB

A

Constituent of Folic acid
Vitamin
Sulfonamides prevent the synthesis of folate by competing with its PAB component

41
Q

Gallic acid

A

Constituent of gall nuts and other vegetable bodies

–> Tannins

42
Q

What yields Tannic acid by its Hydrolysis?

A

Gallic acid and Glucose

43
Q

Use of Gallic and tannic acid

A

Manufacture of inks

44
Q

Homogentisic acid

A

Intermediate in catabolism of aromatic aminos

Could be excreted in large amounts in Urine —> ALKAPTONURIA (dark)

45
Q

o/m/p Benzenedicarboxylic acids

A

Pthalic/Isophtalic + Terephtalic acids

46
Q

Dimethyl phtalate

A

Insect repellent

47
Q

Phtalic anhydride

A

Starting material for organic syntheses

Organic chemistry (16 decks)

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