ALDEHYDES KETONES AND CARBOXYLIC ACIDS.

1. What is the correct IUPAC name of the given compound?

a. 3-ethyl-4-methyl-6-formyl hexanol
b. 4-ethyl-6-hydroxyhexanal
c. 4-ethyl-4-hydroxy-3-methylhexanal
d. 3-ethyl-6-formyl-4-methyl hexanol
2. Common name of the following compound is

a. Salicylaldehyde
b. Cinnamaldehyde
c. Aniline
d. Acetaldehyde
3. Match the following common name given in the column I with IUPAC name given
Column I Column II
a. Cinnamaldehyde I. pentanal
b. acetophenone II. Prop-2-enal
c. Valeraldehyde III. 4 methylpent-3-ene-2one
d. Acrolein IV. 3phenylprop-2-enal
e. mesityl oxide V. 1-phenylethanone

i. (a)- (iv), (b) –(v), c- (i), d-(ii), e-(iii)

ii. (a)- (ii), (b) –(iv), c- (iii), d-(ii), e-(i)
iii. (a)- (iii), (b) –(iv), c- (ii), d-(v), e-(i)
iv. (a)- (ii), (b) –(v), c- (ii), d-(v), e-(i)

4. Assertion: acetic acid does not undergo haloform reaction

Reason: acetic acid has no alpha hydrogen
5. Assertion: formaldehyde is a planar molecule
Reason: It contains sp2 hybridised carbon atom
6. Assertion: boiling point of aldehydes and ketones are higher than hydrocarbons of ether of
comparable masses
Reason: there is a weak molecular association in aldehydes and ketones arising out of the
dipole-dipole interactions
7. Assertion: Aldehyde react with one equivalent of monohydric alcohol in presence of dry HCl
to yield a gem-Di alkoxy compound
Reason: the name of the gemdi alkoxy compound is hemiacetal
8. Assertion: Reaction of C=O group with NH3 derivative is an example of nucleophilic addition
reaction
Reason: reaction is fast when solution contains high concentration
9. Assertion: alkenes are converted to ketones by treating with an acidified aq. solution of PdCl2
Reason: In this process CuCl2 act as a catalyst in presence of air or oxygen
 10. Assertion: the alpha hydrogen atom in carbonyl compound is less acidic
Reason: the anions formed after the loss of alpha hydrogen atom is resonance stabilized

2 marks
11. Write the structures of the given compound
a. 3-fluro-4-hydroxy-4-oxopentanal
b. α- methoxy propionaldehyde
c. 2,4-DNP derivative of acetaldehyde

12. Write short notes on

a. Étard reaction
b. Gattermann Koch reaction
13. Write the products formed when (CH3)3 C – CHO reacts with the following reagents:
(i) CH3COCH3 in the presence of dilute NaOH
(ii) HCN
(iii) Conc. NaOH
14. a. write the structures of compound A, B and C

b. identify aldehyde A
Calcium acetate + Calcium formate A + 2 CaCO3
15. write the products of the following

a.

b.
16. write the products of the following

a.

b.

c.
17. a. Product formed when benzaldehyde is treated with chlorine in absence of catalyst
 b.
17. a. What happens when ethanol is treated with methyl magnesium bromide and then
hydrolysed?
b why is alpha hydrogen more acidic in nature?
c. Why is oxidation of CH3CHO is easier than CH3COCH3 . why?

18. a. arrange the following in increasing order of their reactivity towards nucleophilic addition
reaction
CH3COCH3, HCHO, CH3CHO

b.3 – hydroxy butanal is formed when X reacts with y in dilute Z solution. name X, Y, Z.

19. a. out of benzaldehyde and propionaldehyde which is more reactive towards nucleophilic
addition
b.during preparation of ammonia derivatives of aldehyde and ketones pH of the medium
is controlled why?
20. Explain the reaction of aldehydes with HCN. give the name and structure of intermediate
involved in the reaction

21. Distinguish between

I)C6H5COCH3 and C6H5CHO

II) Propanal and propanone
III) ethanal and propanal

22. I) benzaldehyde gives a positive test with tollens reagent but not with fehlings solution. State
the reason
II) An aromatic aldehyde is treated with acid anhydride in presence of corresponding salt of
acid to give un saturated aromatic acid. Name the type of reaction with an example.
23. An organic compound with the molecular formula C9H10O forms 2,4 -DNP derivative reduces
tollen’s reagent and undergoes Cannizaro reaction. On vigourous oxidation it gives 1,2-
benzenedicarboxylic acid. identify the compound.
24. i)Benzaldehyde can be obtained from benzal chloride. Write reaction for obtaining benzal
chloride and benzaldehyde from it.
ii)why solubility of aldehydes decrease on increasing length of alkyl chain?
25. Read the passage given below and answer the following questions :
The addition reaction of enol or enolate to the carbonyl functional group of aldehyde or ketone
is known as aldol addition. The b-hydroxyaldehyde or b-hydroxyketone so obtained undergo
dehydration in second step to produce a conjugated enone. The first part of reaction is an
addition reaction and the second part is an elimination reaction. Carbonyl compound having
a-hydrogen undergoes aldol condensation reaction.
26. When an aldehyde with no a-hydrogen reacts with concentrated aqueous NaOH, half the
aldehyde is converted to carboxylic acid salt and other half is converted to an alcohol. In other
words, half of the reactant is oxidized and other half is reduced. This reaction is known as
Cannizzaro reaction.
 KK

27. Write the IUPAC names of the following compounds.

(i) (ii) (iii) (iv)

28. Write the structural formula of all the carbonyl compounds with the molecular formula
C5hH10O and name them according to IUPAC system.
29. (i)Suggest the reagents to bring about the following conversion cyclohexanol to bring
cyclohexanone.
(ii)How will you obtain the following ?

from CH3CN
30. (i)Give the chemical equation for the for the following conversion pen-3en-2ol to
pent-3en-2one

(ii)
31. Explain why dialkyl cadmium is considered superior to Grignard reagent for the preparation of
a ketone from an acid chloride.
32. (i)Convert benzene into acetophenone.

(ii)C6H5CHO
33. The number of compounds which do not react with Tollen’s reagent in the following list is

(i) (ii) (iii) (iv) (v)

(vi)
34. Identify the compound A,B and C in the following reaction.
 CH3Br
35. A ketone A which undergoes haloform reaction gives compound B on reduction. B on heating
with conH2SO4 give a compound C which forms monozonide D. D on hydrolysis in the presence
of zinc dust gives only acetaldehyde. Identify A,B,C and D.
36. Give the distinction between
(i)pent-3-one and pentan-2-one. (ii)Acetophenone and benzophenone.
37. Identify the compound A and B in the following reaction.

38. (i) Give the distinction between benzaldehyde and acetophenone.

(ii)how do you convert ethanol to propanone.
39. Predict the products of following reaction.

(i)

(ii)

CARBOXYLIC ACIDS

1. What is the correct IUPAC name of the given compound

a) 2,2-Dimethylbutanoic acid
b) 2-carboxyl-2-methylbutane
c) 2-Ethyl-2-methylpropanoic acid
d) 3-methylbutane carboxylic acid
2. Which of the following is the functional isomer of propanoic acid?
a) Ethylmethanoate
b) Methylethanoate
c) Methylethyl ester
d) Ethylmethyl ether
3. The compound does not liberate CO2 on treatment with aqueous sodium bicarbonate is
____
a) Benzoic acid
b) Benzene sulphonic acid
 c) Salicylic acid
d) Carbolic acid (phenol)
4. The conversion of a carboxylic acid to alpha bromocarboxylic acid using red P and Br2 is
a ___
a) Cannizaro’s reaction
b) Aldol condensation reaction
c) Hell Volhard Zelinsky reaction
d) Kolbe’s reaction
5. Match the acids given in Column I with their correct IUPAC names given in column II.
COLUMN I COLUMN II
a) Phthalic acid i) hexane-1,6-dioic acid
b) Oxalic acid. ii) benzene-1,2-dicarboxylic acid
c) Succinic acid. iii) pentane-1,5-dioic acid
d) Adipic acid. iv) butane-1,4-dioic acid
e) Glutaric acid. v) ethane-1,2-dioic acid
6. Assertion : This compound is named as benzene-1,2-dicarboxylic acid

Reason. : The -COOH group attached to the ring is represented as carboxylic acid
7. Assertion : Acetic acid does not undergo haloform reaction
Reason : Acetic acid has no alpha hydrogen atom
8. Assertion : Compounds containing -CHO group are easily oxidised to corresponding
carboxylic acids
Reason : Carboxylic acids can be reduced to alcohols by treatment with LiAlH4
9. Assertion : The pKa of acetic acid is lower than that of phenol
Reason : Phenoxide ion is more resonance stablized than acetate ion
10. Assertion : Benzoic acid and phenol can be distinguished by NaHCO3
Reason. : Benzoic acid is stronger acid than phenol
11. Assertion : In esterification process, the water or the ester should be removed as soon as it
is formed
Reason : Esterification is the reversible process
12. Assertion : Fluoroacetic acid is stronger than chloroacetic acid
Reason : Due to greater elwctron donating effect of F than Cl
13. Assertion : Acetic acid is weaker acid than CH3CH2COOH.
 Reason : Due to +I effect of methyl group
14. Assertion : The carboxylate ion is more stablized than phenoxide ion
Reason : This is because the negative charge is delocalised over two electronegative
oxygen atoms in carboxylate ions whereas it is less effectively delocalised over one atom
in phenoxide ion
15. Assertion : Rancidity of butter is due to the formation of butanoic acid
Reason. : Under warm and moist conditions glycerides present in butter are hydrolysed
to give butanoic acid
16. Assertion : Nitration of benzoic acid gives m-nitrobenzoic acid
Reason : Carboxyl group increases the electron density at meta position
17. Assertion : o-substituted benzoic acids are generally stronger acids than benzoic acids
Reason : Increased strength is due to ortho effect
18. Assertion : Ketones can be converted into acids by haloform reaction
Reason : Addition of Grignard reagents to dry ice followed by hydrolysis gives ketones
19. Assertion : Carboxylic acids have higher boiling points than alkanes
Reason : Carboxylic acids are resonance hybrids
SHORT ANSWERS
1. Draw the structures of the following. a) 3-Bromo-4-phenylpentanoic acid b) Hex-2-en-4-
yonic acid
2. Write the IUPAC names of the following i) CH3CH=CHCOOH ii) CH3CH2COCH2COOH
iii) CH3CH(OH)CH2COOH
3. 1)Aromatic carboxylic acids do not undergo Friedel Craft’s reaction. Justify.
2)Acetic acid can be halogenated in the presence of red P and Cl2 but formic acid cannot
be halogenated in the same way. Why?
4. Predict the products of the following reactions.
a)

b)

5. Give simple chemical test to distinguish a) benzaldehyde and benzoic acid b) benzoic acid
and ethyl benzoate c) benzoic acid and phenol
6. Distinguish between a) CH3CH2COOH and HCOOH b) Ethanoic acid and ethanoic
anhydride
7. Give chemical test to distinguish between formic acid and acetic acid
8. Formic acid reduces Tollen’s reagent. Explain.
9. Carboxylic acids do not give characteristic reactions of carbonyl group. Justify.
10. Write the mechanism of the following reaction.
CH3COOH+C2H5OH + H+→ CH3COOC2H5+H2O
11. Why does benzoic acid does not undergo Friedel craft reaction? Explain.
12. Account the following.
a) CH3COOH is liquid while aromatic acids are solids
b) Ethanoic acid is weaker than benzoic acid. Why?
c) Why is bond length of C=O in carboxylic acid is slightly larger than that in
aldehyde and ketone?
13. Give reasons
a) Highly branched carboxylic acids are less acidic than unbranched acids. Why?
b) Addition of Grignard reagents to dry ice followed by hydrolysis gives carboxylic
acids whereas that of organolithium compounds under similar conditions give
ketones. Why?
14. A) Why are the boiling points of carboxylic acids higher than those of the corresponding
alcohols?
B) Arrange the following compounds in the increasing order of their boiling point.
CH3CHO, CH3CH2OH, CH3OCH3, CH3CH2CH3
15. Answer the following.
a) Why there is a large difference in the boiling points of butanal and butan-1-ol
b) Arrange the following in decreasing order of their acidic strength and give reason
for your answer. CH3CH2OH, CH3COOH, ClCH2COOH, FCH2COOH,
C6H5CH2COOH
16. Describe how the following conversions are carried out?
a) Toluene to benzoic acid
b) Bromobenzene to benzoic acid
c) Ethyl cyanide to ethanoic acid
d) Butan-1-ol to butanoic acid
17. How will you convert acetic acid into a) malonic acid b) tert-butyl alcohol c) glycine d)
acetylene e) ethylamine
18. How will you make the following conversions.
 a) Propanoic acid to acetic acid
b) Propanoic acid to isopropyl alcohol
c) Ethene to succinic acid
19. Convert the following.
a) Acetic acid to ethanol
b) Propanoic acid to lactic acid
c) Ethanoic acid to propanoic acid

20. .

21.

WORD PROBLEMS

1. Two moles of organic Compound A on treated with a strong base gives two compounds of
B & C. Compound B on dehydrogenation with Cu gives A while acidification of C yields
carboxylic acid D with M.F of CH2O2. Identify A,B,C and D explain the reaction.
2. During practical exams, lab assistant provided two test tube containing 5mL benzoic acid
and 5mL acetaldehyde to every student. A student, Rahul found that test tubes given to
him were unlabelled. He informed the teacher before performing any experiment with the
given chemicals. How can the chemicals be distinguished for correct labelling?
3. An organic compounds A on treatment with ethanol gives carboxylic acid B and
compound C hydrolysis of C under acidified conditions gives B and D. Oxidation of D
with KMnO4 also gives B. B on heating with Ca(OH)2 gives E having molecular formula
C3H6O. E does not give Tollen's test and does not reduce Fehlings Solutions, but forms 2,4
DNP hydrozone. Identify A,B,C,D and E.
4. Compound A was prepared by oxidation of compound B with alkaline KMnO4 compound
A on reduction with LiAlH4 gets converted back to compound B. When compound A is
heated with compound B in the presence of H2SO4 it produces fruity smell of compound
C to which family the compounds A, B and C belong to?