ALDEHYDES, KETONES AND CARBOXYLIC ACIDS

BOARD QUESTIONS

2010

1.What is Tollens’ reagent ? Write one usefulness of this reagent.

2.(a) Illustrate the following name reactions, giving a chemical equation in each case
(i) Clemmensen reaction
(ii) Cannizzaro’s reaction
(b) Describe how the following conversions can be brought about
(i) Cyclohexanol to cyclohexan-1-one
(ii) Ethylbenzene to benzoic acid
(iii) Bromobenzene to benzoic acid
3.(a) Illustrate the following name reactions
(i) Hell-Volhard-Zelinsky reaction
(ii) Wolff-Kishner reduction reaction
(b) How are the following conversions carried out:
(i) Ethyl cyanide to ethanoic acid
(ii) Butan-1-ol to butanoic acid
(iii) Methylbenzene to benzoic acid
Write chemical equations for the involved reactions.

2011

4.Write the structure of the following compound: 3-oxopentanal

5.(a) Give simple chemical tests to distinguish between the following:
(i) Propanal and propanone
(ii) Benzaldehyde to acetophenone
(b) How would you obtain:
(i) But-2-enal from ethanal
(ii) Butanoic acid from butanol
(iii) Benzoic acid from ethylbenzene
6.(a) Describe the following reactions giving a chemical equation in each case:
(i) Cannizzaro’s reaction
(b) Complete
eachsynthesis
by
(ii) Decarboxylation reaction giving missing reagents or products

(b) Complete the following chemical equations:

in the following:

(i)
(( I
COOH SOCl2

~ COOH heat

H2NCONHNH2

(ii) C6H5CHO ~

(iii) 0= CH2 ~0- CHO 5

(a) l-1k"fl~l(gd ';fT1=f
'CiRYit~31T ~ d~I~(UI ~ :

(i) tmro ~ ~

(ii) ~1~~-1 ~~-q~-1

(b) R k"f I ~ R9 d -qj) a:rrq ~ '5rTl:{f ~ :

(i) ~ ~ ~-2-~
(ii) ~~ ~ ~~~ ~
 2012

7.Draw the molecular structure of the compound, 4-methylpent-3-en-2-one

8.Draw the structures of the following compounds:
(i) 3-Methylbutanal
(ii) Hexane-1,6-dioic acid
(iii) p-Nitropropiophenone
9.(a) Illustrate the following reactions giving a suitable chemical equation for each:
(i) Cannizzaro reaction
(ii) Hell-Volhard-Zelinsky reaction
(b) How would you bring about the following conversions ? Write the complete equation in
each case:
(i) Ethanal to 3-hydroxybutanal
(ii) Benzoic acid to m-nitrobenzyl alcohol
(iii) Benzaldehyde to benzophenone
10.Draw the molecular structure of 4-Hydroxy-4-methylpentan-2-one

2013

11.Write the structure of 3-Hydroxybutanal

12.(a) Give reasons for the following:
(i) Ethanal is more reactive than acetone towards nucleophilic addition reaction.
(ii) (CH3)3C-CHO does not undergo aldol condensation.
(iii) Carboxylic acids are higher boiling liquids than alcohols.
(b) Give a simple chemical test to distinguish between
(i) Acetophenone and benzophenone
(ii) Benzaldehyde and ethanal
13.Write the structures of products of the following reactions:
Pd /BaSO4
(i) C6H5-COCl + H2 ?
(ii) CH3-CHO + HCN ?
Conc.KOH
(iii) 2HCHO ?

(iv) O H2NCONHNH2
?
NaOH, CaO

(v) C6H5-COO Na- +

△ ?

14.Write the structure of 4-methylpent-3-en-2-one

15.Write the structural formula of 2-phenylethanoic acid

2014

16.Write the IUPAC name of the following compound

17.(a) Write the products formed when ethanal reacts with the following reagents:
(i) CH3MgBr and then H3O+
(ii) Zn-Hg / Conc.HCl
(iii) C6H5CHO in the presence of dilute NaOH
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7. amCëQ> Ho$ {Z`_ go G$Um _H$ {dMbZ go Š`m Vm n`© h¡ ? EH$ CXmhaU Xr{OE & G$UmË_H$
(b) Give simple
{dMbZ Ho$ {bE chemical tests to distinguish between the following pairs of compounds:2>
mixH H$m Š`m {M• hmoVm h¡ ?
(i) Benzoic acid and ethyl benzoate
(ii) Propanal and butan-2-one AWdm
18.(a) Account for the following:
E{µ(i)
OAmo
CHQ´>m3onCHO
H$mo n[a^m{fV H$s{OE &than
is more reactive amCëQ> CHHo3$COCH
{Z`_ 3gotowards
G$UmË_H$reaction
{dMbZwith
ÛmamHCN.
~ZZo dmbm
E{µ(ii)
OAmoThere are two
Q´>mon {H$g àH$ma-NH
H$m 2hmogroups
Vm h¡ ? inEH$semicarbazide
CXmhaU Xr{OE(H& 2N-NH-CO-NH2). However, only2
one is involved in the formation of semicarbazone.
What
(b) Write is themeant
chemicalbyequation
negative deviation
to illustrate eachfrom
of the Raoult
following s law
name?reactions:
Give an
example.
(i) Rosenmund What reduction
is the sign of mixH for negative deviation ?
(ii) Hell-Volhard-Zelinsky reaction
(iii) Cannizzaro reaction OR
Define azeotropes. What type of azeotrope is formed by negative
2015deviation from Raoult s law ? Give an example.

8. 19.Name
{ZåZ{b{IV A{^{H«used
the reagents $`mAm|in_|the
à`mofollowing
J AmZo dmbo A{^H$maH$m|
reactions: Ho$ Zm_ Xr{OE : 2
?
(i) CH3 CHO CH3 CH CH3
|
OH
?
(ii) CH3 COOH CH3 COCl
20.How do you convert the following:
(i) Benzoic acid to benzaldehyde
Name the reagents used in the following reactions :
(ii) Ethyne to ethanal
(iii) Acetic acid to methane ?
(i) CH3 CHO CH CH CH3
21.Write the equations involved in the3following reactions:
(i) Stephen reaction |
(ii) Wolff-Kishner reduction OH
(iii) Etard reaction ?
(ii) CH3 COOH CH3 COCl
2016
9. (a) Obr` H$m°na(II) ŠbmoamBS> {db`Z Ho$ {d wV²-AnKQ>Z Ho$ Xm¡amZ H¡$WmoS> na
22.An organic compound
{ZåZ{b{IV ‘X’ $having
A{^{H« `mE± hmoVmolecular
r h¢ : formula C4H8O gives orange-red precipitate
with 2,4-DNP reagent. It does not reduce Tollens’ reagent but gives yellow precipitate of
2+ (aq) 0
iodoform onCu heating with+ NaOI.
2e CompoundCu(s) ‘X’ E = + 0·34 V
on reduction with LiAlH4 gives
compound ‘Y’ which undergoes dehydration reaction on heating with Conc.H2SO4 to
form But-2-ene. Identify 1
+ ethe compounds ‘X’ andE‘Y’. 0
H+ (aq) H (g) = 0·00 V
23.Give reasons: 2 2
(i) The ∝-hydrogen
CZHo$ _mZH$ atoms
AnM`Z of aldehydes and (E
BboŠQ´>moS> {d^d ketones
0 are acidic
) Ho$ _mZm| in nature.
Ho$ AmYma na H¡$WmoS> na {H$g
(ii) Propanone is less reactive than ethanal towards
A{^{H«$`m H$s g§^mdZm (gwg§JVVm) h¡ Am¡a Š`m| ? addition of HCN.
(iii) Benzoic acid does not give Friedel-Crafts reaction.
24.How would you convert:
56/2/1/F
(i) Toluene to benzaldehyde 4
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(ii) Ethanoic acid to 2-chloroethanoic acid From: http://www.cbseportal.com
(iii) Acetone to propane
2017

25.Do the following conversions in not more than two steps:

(a) Propene to acetone
(b) Propanoic acid to 2-hydroxypropanoic acid
26.Write the reaction involved in the following
(a) Etard reaction
(b) Wolff-Kishner reduction
27.Give reasons:
(a) Propanone is less reactive than ethanal towards nucleophilic addition reactions.
(b) O2N-CH2-COOH has lower pKa value than CH3COOH.
(c) (CH3)2CH-CHO undergoes aldol condensation whereas (CH3)3C-CHO does not.

2018

28.How do you convert the following:

(a) Ethanal to propanone
(b) Toluene to benzoic acid
29.Account for the following:
(a) Aromatic carboxylic acids do not undergo Friedel-Crafts reaction.
(b) pKa value of 4-nitrobenzoic acid is lower than that of benzoic acid.
30.‘A’, ‘B’ and ‘C’ are three non-cyclic functional isomers of a carbonyl compound with
molecular formula C4H8O. Isomers ‘A’ and ‘C’ give positive Tollens’ test whereas
isomer ‘B’ does not give Tollens’ test but gives positive iodoform test. Isomers ‘A’ and
‘B’ on reduction with Zn(Hg) / Conc.HCl give the same product ‘D’.
(a) Write the structures of ‘A’, ‘B’, ‘C’ and ‘D’
(b) Out of ‘A’, ‘B’ and ‘C’ isomers, which one is least reactive towards addition of
HCN.

2019

31.(a) Carry out the following conversions:

(i) p-Nitrotoluene to 2-bromobenzoic acid
(ii) Propanoic acid to acetic acid
(b) An alkene with molecular formula C5H10 on ozonolysis gives a mixture of two
compounds ‘B’ and ‘C’. Compound ‘B’ gives positive Fehling test and also reacts
with iodine and NaOH solution. Compound ‘C’ does not give Fehling solution test but
forms iodoform. Identify the compounds ‘A’, ‘B’ and ‘C’.
32.(a) Carry out the following conversions:
(i) Benzoic acid to aniline
(ii) Bromomethane to ethanol
(b) Write the structure of major product(s) in the following:
a)H2N - NH2
(i) CH3 – CH2 – C – H b)KOH, Glycol/heat

‖
O
 CH3
I
conc. NaOH
(ii) CH3 – C – CHO
I
CH3
COOH
(iii) NaOH

2020

33.(a) An organic compound ‘A’ having molecular formula C5H10O gives negative Tollens’
test, forms n-pentane, on Clemmensen reduction but doesn’t gives iodoform test.
Identify ‘A’ and give all the reactions involved.
(b) Carry out the following conversions:
(i) Propanoic acid to 2-bromopropanoic acid
(ii) Benzoyl chloride to benzaldehyde
(c) How will you distinguish between benzaldehyde and acetaldehyde ?
34.(a) Complete the following sequence of reactions:
Ba(OH)2 △ NaOH + I2
CH3 CO CH3 ⇌ A ⇌ B C + D
-H2O
(i) Identify ‘A’ to ‘D’
(ii) Give the IUPAC name of ‘A’.
(b) How can you distinguish between
(i) Ethanol and propanone
(ii) Benzoic acid and phenol

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