+2 UNIT 14 PAGE- 3
SOME COMMERCIALLY IMPORTANT CARBOXYLIC ACIDS
1. Formic acid
It is prepared on a large scale by reacting carbon monoxide with aqueous sodium hydroxide under a pressure of 10 atm and 473 K.
Uses : Methanoic acid is used in rubber , leather and electroplating industry.
2. Acetic acid
a. From acetylene
It is prepared from acetylene by reacting with 40% sulphuric acid in the presence of 1% mercuric sulphate (as catalyst), when acetaldehyde is obtained.
Acetaldehyde is then oxidised to acetic acid by passing its vapours mixed with air at about 343 K under pressure over manganese acetate catalyst.
b. From Ethanol
Ethanol is dehydrogenated by passing over copper catalyst at 553 K to get acetaldehyde, which is oxidised to acetic acid.
c. Preparation of Vinegar
Vinegar is dilute solution of acetic acid (7-8%). It is obtained by the fermentation of ethyl alcohol in the presence of enzyme acetobacter in the presence of air.
Uses
1. It is used in the manufacture of rayon and plastics, rubber and silk industries
2. It is used as a solvent.
3. Venegar is used in cooking.
3. Benzoic acid
It is manufactured from toluene, which is obtained from coal tar and petroleum. Toluene is oxidised to benzoic acid by air in presence of V2O5.
Toluene can also be converted to benzoic acid by chlorination followed by hydrolysis.
Uses
1. Benzoic acid and some of its compounds are used as urinary antiseptics.
2. Sodium salt of benzoic acid is used as a food preservative.
3. Its esters are used in perfumery.
Distinction between Alcohols, Phenols and Carboxylic acids
Property | Alcohols | Phenols | Acids |
1. Action on litmus 2. Reaction with NaHCO3 3. Reaction with NaOH 4. Reaction with FeCl3 | no reaction no reaction no reaction no reaction | turns blue litmus red no reaction forms salts gives characteristic colours | turns blue litmus red. Brisk effervescence, evolution of CO2. Form salts no reaction |
FUNCTIONAL DERIVATIVES OF CARBOXYLIC ACIDS
1. ACID HALIDES.
These are the compounds obtained by the replacement of the -OH group of carboxylic acids by the halide group.
Nomenclature
The names of the acyl chlorides are derived from the IUPAC or Common names of the corresponding acids by replacing the suffix -ic acid by -yl chloride. For example :
Formula | CH3COOH | CH3COCl |
Common name | acetic acid | acetyl chloride |
IUPAC name | ethanoic acid | ethanoyl chloride |
2. Acid Amides
They are compounds obtained by replacing -OH group of the carboxyl group by -NH2 group.
Nomenclature
In common system of nomenclature, these are named after the corresponding acid by replacing the suffix -ic acid by amide. According to IUPAC system, these are named by replacing the ending 'e' of the parent hydrocarbon by amide. For example,
Formula | CH3COOH | CH3CONH2 |
Common name | acetic acid | acetamide |
IUPAC name | ethanoic acid | ethanamide |
3. ESTERS
Esters are obtained by replacing -OH group of carboxylic acids by alkoxy group (-OR).
Nomenclature
Esters are named by writing the name of alkyl or aryl group (of OR' part) before the parent acid and changing the suffix 'ic acid' to 'ate'. For example,
Formula | CH3COOH | CH3COOC2H5 |
Common name | acetic acid | Ethyl acetate. |
IUPAC name | ethanoic acid | Ethylethanoate. |
4. Acid anhydrides
These derivatives of carboxylic acids are obtained by the loss of a molecule of H2O from the carboxylic groups.
Nomenclature
These compounds are named as the anhydrides of respective acids both in common and IUPAC systems.
Formula | CH3COOH | CH3CO.O.CO CH3 |
Common name | acetic acid | acetic anhydride |
IUPAC name | ethanoic acid | ethanoic anhydride |
The Common and IUPAC names of functional derivatives of acids are given below:
Esters | ||
Structure | Common name | IUPAC name |
HCOOCH3 CH3COOCH3 CH3CH2COOCH2CH3 C6H5COOCH3 | Methyl formate Methyl acetate Ethylpropionate Methylbenzoate | Methylmethanoate Methylethanoate Ethylpropanoate Methylbenzoate |
Acyl halides or Acid halides | ||
HCOCl CH3COCl CH3CH2COCl C6H5COCl | Formyl chloride Acetyl chloride Propionyl chloride Benzoyl chloride | Methanoyl chloride Ethanoyl chloride Propanoyl chloride Benzoyl chloride |
Acid anhydrides | ||
(CH3CO)2O (CH3CH2CO)2O (C6H5CO)2O | Acetic anhydride Propionic anhydride Benzoic anhydride | Ethanoic anhydride Propanoicanhydride Benzoic anhydride |
Acid amides | ||
HCONH2 CH3CONH2 CH3CH2CONH2 C6H5CONH2 | Formamide Acetamide Propionamide Benzamide | Methanamide Ethanamide Propanamide Benzamide |
ACID CHLORIDES ( R-CO-Cl )
Methods of preparation
1. From Carboxylic Acids
Acyl halides are easily prepared from the carboxylic acids or from their salts by reaction with phosphorus pentachloride, phosphorus trichloride or thionyl chloride.
The reaction is best carried out with thionyl chloride because other products are gases.
2. From salts of carboxylic acids
The acid chlorides are prepared by the distillation of sodium or calcium salts of carboxylic acids with phosphorus trichloride, phosphoryl chloride or sulphuryl chloride(SO2Cl2).
Physical properties
1. Lower members of the family are colourless liquids, whereas the higher members are colourless low melting solids.
2. The acid halides generally fume in air and have pungent and irritating smell. When exposed to atmosphere, these are hydrolysed to give fumes of hydrogen chloride.
3. These are insoluble in water due to the lack of hydrogen bonding with water molecules. However, they are soluble in common organic solvents such as ether, chloroform, acetone, benzene etc.
4. The boiling points of acid chlorides are lower than those of parent carboxylic acids. The low boiling points of acid halides is due to the absence of intermolecular hydrogen bonds. For example, acetic acid boils at 391 K, while acetyl chloride boils at 326 K.
Chemical properties
Among the different derivatives of carboxylic acids, acyl chlorides are probably the most reactive compounds. The important chemical reactions of acyl chlorides are:
1. Acylation reactions
Acyl halides are vigorous acylating agents. They react with water to give carboxylic acids (Hydrolysis) alcohols to give esters (alcoholysis) ammonia to give amides (ammonolysis ) carboxylic acids or carboxylate ions to give acid anhydrides.
In the above reaction , if the acid halide used is benzoyl chloride(C6H5COCl), then these reactions are termed as benzoylation reaction. The reaction with aromatic acyl chlorides is carried out in the presence of a base such as sodium hydroxide or pyridine. This reaction is called Schotten Baumann reaction.
2. Friedel Craft's acylation
With benzene , acyl halides react to form ketones. The reaction is known as Friedel Craft's Acylation.
3. Catalytic hydrogenation
Acyl halides are reduced to aldehydes by the action of hydrogen in the presence of Pd -BaSO4 containing some sulphur or quinoline produce aldehydes.
The reaction is known as Rosenmund's reduction.
Reduction with LiAlH4 primary alcohols are produced.
4. Reaction with dialkyl cadmium : Acyl halides react with dialkyl cadmium to form ketones
5. Reaction with KCN : Acyl chlorides react with potassium cyanide solution to form alkanoyl cyanides.
6. Reaction with AgNO3 : As the aliphatic acyl chlorides are readily decomposed by water, therefore an aqueous solution of acyl chlorides gives a white precipitate with AgNO3. 
ACID ANHYDRIDES
Methods of Preparation
1. From Carboxylic Acids : Acid anhydrides are prepared by heating carboxylic acids in the presence of P2O5.
2. From Carboxylic salt and acyl chloride : Salts of carboxylic acids are treated with acid chlorides in the presence of pyridine. 
Physical properties
1. Lower aliphatic anhydrides are colourless liquids with sharp irritating smell. The higher members are generally insoluble in water, but are soluble in organic solvents such as ether, acetone, alcohol etc.
2. The higher members of the family as well as the aromatic acid anhydrides are solids.
3. The boiling points of acid anhydrides are higher than those of carboxylic acids from which they are formed. This is because of the greater size of the acid anhydride molecule as compared to that of acid.
Chemical properties
These are used in acyl reactions in preference to acyl chlorides because the reactions are not vigorous and can be easily controlled. The common reactions are :
1. Hydrolysis : Acid anhydrides are hydrolysed to give acids.
2. Reaction with alcohols : Acid anhydrides react with alcohols to form esters and acids.
3.Reaction with ammonia (ammonolysis) : Acid anhydrides react with ammonia to form amides.
With amines, the acid anhydrides form substituted amides.
4. Reaction with Benzene : Acid anhydrides react with benzene to form ketones.
5. Reduction : Anhydrides are reduced by LiAlH4 to give alcohols.
ESTERS
Methods of preparation
Esters are prepared by the treatment of alcohols with carboxylic acids, acid halides or anhydrides
1. From Carboxylic acids : Esters are generally prepared by heating carboxylic acids with alcohols in the presence of a few drops of Con. H2SO4 or dry HCl gas.
The reaction is reversible in nature and is known as esterification. The reaction is carried out to completion by using excess of a reactant or by removing the water from the reaction mixture.
Methyl esters can be prepared by treating carboxylic acid with diazomethane in ether solvent.
2. From acid chlorides or acid anhydrides : Esters are easily prepared by the action of alcohols on acid chlorides or acid anhydrides.
3. From Alkyl halides : Esters are prepared by treating alkyl halides with silver salts of carboxylic acids.
Physical Properties
1. Esters are colourless liquids (or solids) with characteristic fruity smell. Because of their characteristic odours, they find applications in the manufacture of artificial flavouring extracts and perfumes. Flavours of some esters are listed below.
Ester | Flavour | Ester | flavour |
amyl acetate | banana | Isoamyl formate | raspberry |
Benzyl acetate | jasmine | Ethyl butyrate | pineapple |
Amyl butyrate | apricot | Octyl acetate | orange |
2. They are sparingly soluble in water, but readily soluble in organic solvents such as alcohols, ether etc.
3. The boiling points of esters are always less than the corresponding acids because esters do not form hydrogen bonds.
Chemical Properties
The important chemical properties of esters are given below :
1. Hydrolysis : Esters are slowly hydrolysed by water at reflux temperatures. The reaction is accelerated by dilute mineral acids (HCl, H2SO4) or alkalies. Hydrolysis of esters by alkalies is also known as saponification. It is very rapid because alkalies act as a catalyst and also react with the acid formed as a product of reaction. Consequently, the equilibrium is shifted in the forward direction.
2. Reaction with ammonia (ammonolysis) : On reacting ammonia, esters give amides.This reaction is known as ammonolysis of esters.
3. Reduction : Esters are reduced to alcohols with LiAlH4 or refluxing with sodium and alcohol.
4. Reaction with phosphorus pentachloride : Esters react with PCl5 to form acid chlorides.
5. Alcoholysis : An ester on refluxing with a large excess of an alcohol in the presence of a little acid or alkali, undergoes exchange of alcohol residues, ie., alkoxy parts as shown below:
This reaction is known as alcoholysis or trans-esterification.
6. Reaction with Grignard Reagent: All esters except the esters of formic acid react with Grignard reagent to give tertiary alcohols. The esters of formic acid gives secondary alcohols.
7. Claisen Condensation : The esters which have at least one a-hydrogen atom undergo self condensation in the presence of strong base such as sodium ethoxide to form b-ketoesters.
This reaction is called Claisen Condensation.
Uses of esters
1. Esters are used as artificial fruit flavours for making essences.
2. These are used as industrial solvents for lacquers , oils, fats varnishes, etc.
3. High boiling esters like n-butyl phthalates are used as plasticizers for resins and plastics.
ACID AMIDES
Methods of Preparation
1. Ammonolysis of acid derivatives (Acid chlorides or Acid anhydrides ): Acid amides are prepared by the action of ammonia with acid chlorides or acid anhydrides.
Most of the acid amides are usually formed from acid chlorides by the action with ammonia or amines.
2. From Ammonium salts of Carboxylic acids : Amides can be prepared by heating ammonium salts of carboxylic acids.
3. By partial hydrolysis of alkyl cyanides ( Nitriles) : The partial hydrolysis of alkyl cyanides with with cold Con. HCl or H2SO4 give amides.
Physical properties
1. Formamide is a liquid while all other amides are solids.
2. Amides have high boiling points than the corresponding acids. For example,
Acetic acid ( b.p = 391 K ) Acetamide ( b.p = 494K )
Benzoic acid ( b.p = 522 K ) Benzamide ( b.p = 563 K) The higher boiling points of amides is because of intermolecular hydrogen bonding as shown below.
Chemical Properties
1. Amphoteric Nature : Unlike amines, amides are not appreciably basic. This is due to the fact that the nitrogen atom in amides is involved in resonance with carbonyl group. For example, the three resonating forms of acetamide are shown below :
Structure (III) shows that the lone pair on the nitrogen atom is not available for protonation. Therefore, the basic character of acetamide is considerably decreased. Thus acetamide is a weaker base than ethyl amine.
However, under suitable conditions, the amides can behave as weak acids. In other words, amides have amphoteric character. Acetamide (as base) reacts with hydrochloric acid to form a salt.
Acetamide(as acid) reacts with mercuric oxide(a base) to form mercury salt and water. 
2. Reduction: Amides can be easily reduced with sodium and ethyl alcohol or by means of Lithium aluminium hydride to form primary amines.
3. Dehydration : Amides on heating with phosphorus pentoxide or thionyl chloride get dehydrated to form cyanides. For example,
4. Hydrolysis : Amides are hydrolysed on boiling with dilute acid or alkalies. For example,
5. Reaction with nitrous acid : Amides react with nitrous acid to give carboxylic acids and nitrogen gas. Nitrous acid required is prepared insitu by reaction of NaNO2 and HCl.
6. Action with bromine and caustic alkali (Hoffmann bromamide reaction) : Amides react with bromine in the presence of caustic alkali to form primary amine carrying one carbon atom less than the parent amide.
This reaction is useful in stepping down in a family (convert higher member in a family into a next lower member).
Uses of acid amides
1. Primary amides are commonly used for the preparation of primary amines.
2. Amides such as dimethyl formamide (DMF), dimethyl acetamide(DMA) are used as solvents for polar and non-polar compounds.
Problems
01. Write chemical reactions to effect the following transformations :
(a) Butan-1-ol to Butanoic acid
(b) Benzyl alcohol to phenylethanoic acid.
(c) Bromobenzene to Benzoic acid
(d) P-Methylacetophenone to Benzene-1,4-dicarboxylic acid
(e) Cyclohexene to Hexane-1,6-dioic acid
02. Arrange the following compounds in increasing order of their boiling points ; acetic acid, Methyl formate, acetamide, Propan-1-ol.
03. Write chemical reactions to effect the following transformations :
(a) Benzoic acid to benzyl amine
(b) p-Nitrobenzoic acid to benzyl amine.
(c) Hexanoic acid to Hexane nitrile.
04. How will you convert hept-1-ene to :
(a) Heptanal
(b) Hexanal
(c) Hexanoic acid
(d) Heptanoic acid
05. Which of the following compounds would undergo aldol condensation , which the Cannizaro’s reaction and which neither ? Write the structures of the expected products of Aldol condensation and Cannizaro’s reaction.
(a) Methanal
(b) 2-Methylpentanal
(c) Benzaldehyde
(d) Benzophenone
(e) Cyclohexanone
(f) 1-Phenylpropanone
(g) Phenylacetaldehyde
(h) Butan-1-ol
(i) 2,2-Dimethylbutanal
06. How will you convert acetaldehyde into the following compounds ?(N)
(a) Butan-2-one
(b) Butane-1,3-diol
(c) But-2-enal
(d) Butan-1-ol
(e) Butanoic acid
07. Write structural formulae and names of the four possible aldol condensation products from propanal and butanal.
08. An organic compound with the molecular formula C9H10O forms 2,4-DNP derivative, reduces Tollen’s reagent and undergoes Cannizaro’s reaction. On vigorous oxidation , it gives 1,2-Benzenedicarboxylic acid . Identify the compound.
09. How will you convert formaldehyde to acetaldehyde and vice versa ?
10. How will you convert acetic acid to :
i) malonic acid ii) tert-butyl alcohol iii) Glycine
iv) acetylene v) ethyl amine
11. Compound (A) C6H12O2 on reduction with LiAlH4 gave two compounds (B) and (C) . The Compound (B) on oxidation gave (D) which upon treatment with aqu. alkali and subsequent heating gave (E). The latter on catalytic hydrogenation gave (C). The compound (D) was oxidised further to give F which was found to be monobasic (molecular mass = 60). Deduce the structures of A, B, C, D and E.
12. An organic compound A having the molecular formula C3H8O on treatment with copper at 573 K gives B. B does not reduce Fehling solution but gives positive iodoform test. Write down the structural formula of A and B.
13. What happens when :
i) Ethyl acetate is reduced with LiAlH4.
ii) Acetone is reduced with hydrogen in the presence of Ni or Pt.
iii) Sodium acetate is heated with soda lime
iv) Benzophenone is reduced with Zn/Hg in the presence of HCl.
14. How are the following compounds prepared ?
i) Benzaldehyde from benzoyl chloride
ii) Acetophenone from acetylene
iii) Acetic acid from acetylene
iv) Benzamide from benzoic acid
v) 2-Propanol from propanone.
15. How will distinguish between :
i) 2-Pentanone and 3-Pentanone
ii) Phenol and benzoic acid
iii) Propanal and propanone
16. Predict the organic products of the following reactions :
17. Identify the compounds (A) – (F) in the following reactions :
Questions
1. What are ethers ? How are they named ?
2. How are symmetrical ethers differ from unsymmetriical ethers
3. What are aldehydes ? How are they named ? Give some examples to illustrate it.
4. What are ketones ? How are they named ? Cite some examples to illustrate it.
5. What are carboxylic acids ? Give their nomenclature and classification.
6. What are esters ? Give their nomenclature with examples.
7. What are acid amides ? Give their nomenclature with examples.
8. What are acid anhydrides ? Give their nomenclature with examples.
9. Give the IUPAC names of the following.
i) Diethyl ketone) vi) Butyric acid acetone
ii) Ethyl methyl ketone vii) Oxalic acid
iii) Acetaldehyde viii) Acetic acid
iv) Methyl propyl ketone ix) 2-Methyl acetic acid
v) Formic acid
10. Give the IUPAC names of the following :
i) CH3COCH(CH3)CH3 vi) CH3CH2COOH
ii) C6H5CH2COOH vii) CH3COC2H5
iii) CH3(CH3)CHCH2CHO viii) CH3CH(C2H5)CHO
iv) CH3CHO ix) CH3CH(COOH)CH2CH3
v) CH3CH2COCH3 x) HOOCCOOH
11. Give the structures and IUPAC names of :
i) Nine isomeric esters of formula C5H10O2.
ii) Seven isomeric esters of formula C5H10O2.
iii) Seven carbonyl compounds of formula C5H10O.
12. Give the general methods of preparation of ethers.
13. Write the IUPAC name of diethyl ether. How will you obtain it from ethanol ?
14. Account for the following :
i) Ether has a lower dipole moment than alcohol
ii) Ethers behave as weak bases.
iii) Ethers are soluble in water.
iv) Solubility of ethers in water decreases, if water is saturated with common salt.
15. Discuss the general chemical properties of ethers.
16. The boiling points of ethers are lower than their isomeric alcohols. Give reason.
17. Give a method of preparation of methoxy benzene. How does it react with con. HNO3 + Con H2SO4 mixture ?
18. Describe the general methods of preparation of aldehydes and ketones.
19. The boiling points of aldehydes and ketones are lower than the corresponding alcohols and acids. Give reasons.
20. Discuss important chemical properties of aldehydes and ketones.
21. Give the reactions of :
i) acetone with HCN
ii) acetaldehyde with dilute alkali.
iii) C2H5MgBr iv) NaHSO3
22. Write notes on :
i) Condensation ii) Polymerisatrion.
23. How does the following substances react ? Give balanced chemical equations and names of major products.
i) Acetone and phenyl hydrazine
ii) Formaldehyde and NaOH
iii) Acetaldehyde and dil. NaOH
24. Give the products of the reaction 
25. Indicate the structure of the organic product expected, when acetaldehyde is treated with a few drops of concentrated sulphuric acid.
26. What is the IUPAC namr of methyl tert butyl ether ? Write one method each for the synthesis and cleavage of ether linkage.
27. How are the aldehydes distinguished from ketones using Tollen's and Fehling reagents ? Give the complete chemical reactions.
28. Give the reactions in which aliphatic aldehydes differ from aliphatic ketones.
29. How will you obtain aldol from acetaldehyde ?
30. How will you detect the presence of carbonyl group in an organic compound ?
31. How can you purify a carbonyl compound ? Give the chemistry involved in it.
32. What is the action of sodium hydroxide on benzaldehyde ?
33. Give one chemical test to distinguish between formaldehyde and acetone.
34. State suitable test to distinguish between ethyl alcohol and acetaldehyde.
35. Write suitable colour tests or reactions by which propanol and acetone may be distinguished.
36. How will you distinguish between the following ?
C6H5COCH3, C6H5CH2CHO , C6H5COCH2CH3.
37. How would you differentiate an aldehyde from a ketone ?
38. Give methods of preparation of benzaldehyde.
39. Give the reactions of benzaldehyde which are not shown by aliphatic aldehydes.
40. Give the main differences between benzaldehyde and acetaldehyde.
41. Write notes on :
i) Rosenmund's reduction vii) Perkin's reaction
ii) lliamson's synthesis viii) Gattermann's reaction
iii) Kolbe's reaction ix) Claisen condensation
iv) Aldol condensation x) Etard's reaction
v) Cannizaros's reaction xi) Kolbe's electrolysis
vi) Acetylation xii) Benzoin condensation.
42. For isomeric aldehyde and ketone pair give :
i) two reaction which are common
ii) two reactions which are different
43. What are aldehydes and ketones ? How acetone and acetaldehyde be prepared from CH3COCl. Why are aldehydes more reactive than ketones towards nucleophilic reagents.
44. Explain the following :
I) Protonation
II) Fehling solution
III) Tollen's reagent
iv) Trans-esterification.
45. Write the names and structures of the products formed in the following reactions:
i) Reaction of acetyl chloride with hydrogen in the presence of palladium as catalyst.
ii) Oxidation of toluene with chromic oxide in acetic anhydride.
iii) Friedel-Craft's reaction between acetyl chloride and toluene in presence of aluminium chloride.
iv) Dehydrogenation of propanol over heated copper.
v) Addition of HCN to acetaldehyde.
vi) Addition of NaHSO3 to acetaldehyde.
vii) Reaction of ethyl magnesium bromide with 2-butanone
viii) Reaction of semicarbazide with formaldehyde.
46. How are the following compounds prepared ?
i) Diethyl ether from ethyl iodide
ii) Acetophenone from benzene
iii) Benzaldehyde from benzoyl chloride
iv) 2-Propanol from propanone.
47. How is acetic acid prepared ?
48. How may acetic acid prepared from acetylene ?
49. Give the methods for the preparation of benzoic acid.
50. Give the general chemical properties of carboxylic acids.
51. The boiling points of acids are higher than the corresponding alcohols. Give reasons.
52. What is the action of chlorine on acetic acid ?
53. Give the reaction of phosphorus pentachloride on acetic acid.
54. Why the pKa value for trichloroacetic acid lower than that of acetic acid ? How can we obtain methane and acetic anhydride from acetic acid.
55. Taking a suitable example of an acid, describe the formation of an ester, an amide and anhydride.
56. Write a note on ring substitution in benzoic acid.
57. How do the following substances react ?
i) Calcium oxalate reacts with dil. Sulphuric acid.
ii) Potassium permanganate solution is added to cold acidified solution of oxalic acid.
58. Write the names and structures of the products formed in the following reactions:
i) Reaction of thionyl chloride with benzoic acid
ii) Oxidation of ethyl benzene with alkaline KMnO4.
59. Complete the following reactions:
60. Write the balanced chemical equations for the following reactions:
i) Thionyl chloride reacts with benzoic acid
ii) Decarboxylation of malonic acid.
61. How will you obtain acetic acid from methanol ? How may acetic acid be converted into ethane ?
62. How are the following compounds prepared ?
i) Acetylene to acetic acid
ii) Ethyl propanoate from propanoic acid and ethanol.
iii) Acetic anhydride from acetic acid
iv) Benzamide from benzoic acid
63. How will convert:
i) Carbon monoxide to oxalic acid
ii) Oxalic acid to dimethyl oxalate
iii) Toluene into benzoic acid
iv) Acetic acid to acetone
v) Acetyl chloride to acetone
vi) Benzene to benzaldehyde
vii) Formic acid to disodium oxalate
viii) Acetic acid to methane
ix) Sucrose to oxalic acid
x) Acetic acid to propionic acid
xi) Acetaldehyde into formaldehyde
xii) Benzene to benzoic acid
xiii) Ethylene to acetic acid
xiv) Acetylene into acetaldehyde
xv) Chlorobenzene to salicylic
xvi) Ethylene to acetic acid
xvii) Methyl magnesium bromide into acetaldehyde.
xviii) Phenol to salicylic acid
xix) Acetylene to acetic acid
xx) Methyl magnesium bromide into acetone
xxi) Benzene to salicylic acid
xxii) Methanol to ethanol
xxiii) Methyl magnesium bromide to acetic acid
xxiv) Acetylene to acetone
xxv) Acetic acid to trichloroacetic acid
xxvi) Acetyl chloride to acetaldehyde
xxvii) Acetone to 2-Methyl-2-Propanol
64. How will you convert :
i) Propanoic acid to acetic acid
ii) Acetophenone to benzoic acid
iii) anisole to o-nitroanisole
iv) acetophenone to ethylbenzene
v) acetamide to ethyl amine
vi) propanoic acid to propanol
65. >C=O group behaves differently in aldehydes and acids. Account for it.
66. How will you account for the following:
i) Chloroacetic acid is stronger than acetic acid.
ii) The order of reactivity of halogen acids with alcohols is HI > HBr > HCl.
iii) In the preparation of ester by the reaction of a carboxylic acid and an alcohol, the ester is distilled as fast as it is formed.
iv) During the preparation of ammonia derivatives from aldehydes and ketones, the pH of the reaction is carefully controlled.
v) Phenyl methyl ether reacts with HI to give phenol and methyl iodide and not iodobenzene and methyl alcohol.
67. Write suitable tests of phenol and acetic acid.
68. How can you distinguish between ethanol (alcohol) and acetic acid(carboxylic acid) ?
69. Give general methods of preparation and properties of acid chlorides.
70. Give the general methods of preparation and properties of acid anhydrides.
71. Give the general methods of preparation and properties of acid amides.
72. Account for the following :
i) Boiling point of acetyl chloride is less than that of acetic acid
ii) Boiling points of acetic anhydride is higher than the acid from which it is derived.
73. Arrange the following in the increasing order of boiling points. Give reason in support of your answers.
i) C3H8, C2H5OH, CH3OCH3, CH2OHCH2OH
ii) C3H8, C2H5OH, CH3CHO, CH3COOH
iii) 3-Pentanol, n-Pentane, 2,2-Dimethylpropanol, CH3COOH
iv) CH3COCl, (CH3CO)2O, CH3CONH2, CH3COOH.
74. Arrange following compound in increasing order of acidity. Give reason for your answer.
(a) C6H5OH ; C6H5COOH ; C6H5CH2OH
(b) C3H7COOH ; CH3CH2CHBrCOOH ; CH3CHBrCH2COOH
(c) C6H5COOH ; p-O2NC6H4COOH ; p-CH3C6H4COOH
75. Arrange the following sets of compounds in order of their solubility in water. Give reason in support of your answer.
(a) C6H5CH2OH ; C6H5CH2OCCH3 : C6H5CH2CH3 : p-H3CC6H4COOH and p-HOC6H4CH2OH
76. Explain the following about acetic acid :
i) Its boiling point is higher than that of n-propanol.
ii) It is weaker acid than chloroacetic acid.
77. An organic compound A (C7H7Cl) on oxidation with KMnO4 yields a monobasic acid, C7H6O2. Distillation of calcium salt of this monobasic acid with slaked lime gives a hydrocarbon, whose vapour density is 39. Give the structures of A and B.
78. Identify the substances X, Y and Z in each of the following.
79. Identify A, B and C in the following reaction. 
80. An organic compound A (C4H10O) is optically active. On mild oxidation , it gives a compound B(C4H8O), but on vigorous oxidation it gives another compound C(C3H6O). C along with D is also formed from B by reaction with iodine in the presence of alkali. Deduce the structures of A, B and C.