294

wtG Objectiye NCERT

Thus. strongelectron
R
group and resonance
base are responsible for wistatthebh1ldriaswatiinogn etfecthe
of
oi

0:
R
atoms of carbonylcompoundsacidity of
Aldehydes and ketones
cconatgbn o
() () (1) atom undergo reactioncontaining atleast
a in
Resonancestabilisation of carboxvlate anion is more alkali as catalyst to he
(aldol) or ß-hydroxy ketoncs. presence ofonmedirHhte
forrm
than that ot undissociated carboxyic acid. Therefore.
greater stability of carboxylate ion is responsible tor
the acidic character of carboxylic acids.
5 Binthe f-hydroxy
following sequence is aldehvder
1. The strongest acid among the following is dil \aOtt,AZnHg
(a) salicylic acid HC>B
(b) m-hydroxvbenzoic acid (a)
(c) p-hydroxybenzoic acid (b)
(d) benzoic acid. OH OH
2. Arrange the following carboxylic acids in their
decreasing acidity : (c) (d)
(1) ÇOOH Oxalicacid
OH
COOH
OH
(2) HOOC-CH,-COOH Malonic acid 6. How many aldols are formed
when
(3) CH,-COoH Succinic acid
and
(a) 2
propanaldehyde undergo aldol
(b) 4 (c) 3 acetaldehvde cond(d)ensa8tion?
CH,-COOH 7. Astrong base can abstract
an
(a) 3> 2>1
(c) 2> 3>1
(b) 1> 2 >3
(d) 2>1>3
(a) ketone (b) a-hydrogen(d) tromamin.
alkane (c) alkene
8. A compound
3 In the anion HCOO, the two carbon-oxygen bonds possessing a-hydrogen atom, in the
presence of dilute
are found to be of equal length. What is the reason alkali
This product on heatingforms B-hydroxy aldehvàe
for it? with dilute acid forms an
(a) Electronic orbitals of carbon atom are unsaturated crotonaldehyde.
The compound is
(a) CH,CHO (b) CH,CH,CHO
hybridised. (c) CH, CH- CHO (d)
(b) The C-0 bond is weaker than the C-Cbond.
(c) The anion HCO0 has two resonating structures. 3. HCEC-CHO
Aldehydes differ from ketones in their oxidation
(d) The anion is obtained by removal of a proton reactions. Aldehydes are easily oxidised to
from the acid molecule. carboxylic acids containing the same number of
carbon atoms because aldehydes contain H-atom
4 Which of the following has the maximum acidic attached tocarbonyl group, which can be converted
strength? into -OH group without involving the cleavage of
(a) o-nitrobenzoic acid (b) m-nitrobenzoic acid
(c) any other bond. Thus, they are oxidised not only
p-nitrobenzoic acid (d) p-nitrophenol by strong oxidising agents like HNO, KMn0, and
The carbon atom next to carbonyl group is called K,Cr,0, but also by weak oxidising agents lie
0-carbon atom and hydrogens attached to -carbon Tollens' reagent, Fehling's solution and Benedits
atom are
-hydrogens. Due to strong electron reagent.
withdrawing effect of carbonyl group, the c-carbon R-CHO + [0] R-COOH
atom becomes electron deficient which in turn, Aldehyde Carboxylic acid
withdraws electrons from C-H bond. As a result, Unlikealdehydes, ketones do not contain H-alon
the electron density in Co-H bond decreases and cannot
hence, a-H atom becomes weakly held which can attached to C=0 group and hence, thhevTheseare
agents.
be oxidised by weak oxidising
be easily abstracted by strong bases agentslke
ion which is stabilised by resonance forming enolate
as given below: generally oxidised by strong oxidising
IK,CrO-athigh
HNO, acidified KMnO., , acidified
Ö: temperature. seleniumdioxide
9 Oxidation of acetaldehvde with
produces (b) oxalicacid
H :B (a) glyoxal (d) methanoicacid.
Resonance stabilised enolate anion
(c) ethanoicacid