neet 2024 SPeciAL

CHAP TE R

LEVEL - I 12
Aldehydes, Ketones and
Carboxylic acids
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Chemistry
Chemistry

CONTENTS
COMMON CARBONYL COMPOUNDS
Aldehydes, Ketones and Carboxylic acids

COMMON NAMES

STRUCTURE OF CARBONYL COMPOUNDS

ALDEHYDES AND KETONES

CARBOXYLIC ACIDS

“Organic chemistry gives me the most remarkable things, a

monstrous and boundless thicket, with no way to escape, into
which one may well dread to enter.”
— Friedrich Wohler
Aldehydes, Ketones and Carboxylic acids

12.1 COMMON CARBONYL COMPOUNDS

‹ Compounds containing carbon doubly bonded to oxygen atoms are known as carbonyl
compounds.
‹ Carbonyl compounds find extensive usage in our daily life, and most of them go unnoticed.

CHO
CHO CH = CHCHO
OH

OCH3
OH
Vanillin Salicylaldehyde Cinnamaldehyde

Vanillin is the ingredient that imparts flavour to the “vanilla” ice-cream and many other
delicacies; it is found in vanilla beans. Salicylaldehyde (salicylic acid, which is derived from
this compound and is taken as a painkiller) and cinnamaldehyde (found in cinnamon) have
been very pleasant.
Aldehydes such as camphor, vanillin and butyraldehyde are used for their pleasant fragrance.

Formalin is a solution of 40% solution of formaldehyde in

water. It is used for the preservation of animal specimens
and also as a starting material for Bakelite.

12.2 COMMON NAMES OF CARBONYL COMPOUNDS

When we look at the reactions of the carbonyl compounds, the reactions are mostly taken
at the carbonyl carbon, α-C, β-C and so on. Therefore, it is crucial to know by what name
the reaction centres are called.
CH3
H2
CH β C H
γ α
H 3C C C
H2
O

01
 Chemistry

Some other carbonyl compounds with their commonly used names:

O

H
C
O
H 3C O
acetaldehyde Benzaldehyde acetophenone

Benzophenone γ-methylcyclohexanecarbaldehyde

O O

O C CH3
H2
CH3
-Methylcyclohexanone Acetoacetaldehyde

12.3 STRUCTURE OF CARBONYL COMPOUNDS

The carbonyl carbon atom is sp2 hybridised. C=O bond is partially polarized due to the
higher electronegativity of oxygen relative to carbon. The presence of a double bond also
renders planar nature to >C=O.

120⁰

bond C O
120⁰ C O

120⁰

σ bond

The carbonyl C has a partial positive charge, and the oxygen has a partial negative
charge; therefore, the former act as an electrophile and the latter act as a nucleophile.

02
Aldehydes, Ketones and Carboxylic acids

The group R-C=O is generally known as an acyl group

in common chemistry jargon. There are compound
names which are derived if this group is present in the
compound.
O

H 3C C O
H2

aceto acetaldehyde

12.4 PREPARATION OF ALDEHYDES & KETONES

Some chemical reactions involving alcohols and hydrocarbons, also lead to the formation of
aldehydes and ketones. Some of the reactions are listed below:

Dehydrogenation of primary &

Oxidation of alcohols
secondary alcohols

Ozonolysis of alkenes Hydration of alkynes

Note: All the above reactions have been covered in previous chapters.

12.4.1 PREPARATION OF ALDEHYDES

From acyl chlorides
The reaction which is used to synthesise benzaldehyde from benzoyl chloride using
Pd and BaSO4 (Lindlar's catalyst) catalysts for hydrogenation(AIPMT 2002, 2013)

O
C CHO
H2
Cl
Pd-BaSO4

Benzoyl chloride Benzaldehyde

Rosenmund Reduction

03
 Chemistry

From Nitriles and esters

If we take the nitriles and esters as substrate, and use SnCl2 and HCl as the
attacking reagents, imine is formed in the process and work up leads to the
formation of an aldehyde.
+
H3 O
RCN + SnCl2 + HCl → RCH
= NH → RCHO

Stephen Reaction
O O
1. DIBAL-H
CH3(CH2)9 C OC2H5 2. H2O
CH3(CH2)9 C H

Nitriles are also reduced by DIBAL-H to imines which gives an aldehyde on hydrolysis.

From hydrocarbons
Oxidation of methylbenzene (AIPMT 1996)

Oxidation of methylbenzene (Etard Reaction) (AIPMT 1996)

Oxidation of Toluene by chromyl chloride followed by hydrolysis give benzaldehyde.
CH3 CH(OCrOHCl2)2 H3O+
CHO
CS2
CrO2Cl2

Toluene Chromium complex Benzaldehyde

Use of chromic oxide

Chromium oxide gives benzylidene diacetate from toluene, which on aqueous acid
treatment gives benzaldehyde.
CH3 CH(OCOCH3)2 CHO
273-283K H3O+
CrO3 /(CH3CO)2O

Benzaldehyde

Side chain chlorination (NEET 2020)


Benzal chloride prepared by chlorination of toluene in the presence of hν/sunlight
gives benzaldehyde on hydrolysis.
CH3 CHCl2 CHO
Cl2/hv H 2O
373 K

Toluene Benzal chloride Benzaldehyde

04
Aldehydes, Ketones and Carboxylic acids

Treatment of benzene and its derivatives with CO and HCl

Benzene gives benzaldehyde when treated with carbon monoxide and HCl in
presence of anhydrous AlCl3 or cuprous chloride.
CHO
CO, HCl
Anhyd. AlCl3/CuCl

Benzene Benzaldehyde
Gatterman Koch Reaction

-
DIBAL-H stands for Diisobutylaluminium H
NCERT
hydrides and it acts as a strong reducing Al
+ Highlights

agent.

12.4.2 PREPARATION OF KETONES

From acyl chlorides
Dialkyl cadmium converts acylchlorides to ketones.
2R Mg X CdCl2 R2Cd 2Mg(X)Cl

2 R′ C Cl R2Cd 2R′ C R + CdCl2

O O

From nitriles
Nitriles, when treated with Grignard reagent forms imine intermediate, which on
hydrolysis gives corresponding ketone.
NMgBr O
ether H3O+
CH3 C≡N CH3 C CH3 C
C6H5MgBr
C 6H 5 C6H5
Acetophenone

From benzene/substituted benzenes

Friedel-crafts acylation of benzene or substitutes benzene gives ketones.
O
O
Anhyd. AlCl3 C
Ar/R
Ar/R – C – Cl

Friedel-Crafts acylation

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 Chemistry

12.4.3 PHYSICAL PROPERTIES

Except for As the length of Solubility in water Due to
methanal, all the the alkyl chain is only limited to dipole-dipole
other aldehydes increases, the lower members interactions, the
and ketones smell changes of aldehydes and boiling point of
are liquid or from pungent to ketones. aldehydes and
solid at room pleasant. All the non- ketones are
temperature. polar solvents higher than other
solubilize carbonyl hydrocarbons
compounds. but lower than
alcohols.

H O H
C H H C
R O O R

NCERT
The lower members of the carbonyl compounds, such as methanal, Highlights

ethanal and propanone, are soluble in water due to hydrogen bonding.

As the chain length increases, the non-polar component of the chain
increases which leads to a decrease in the solubility for higher aldehydes
and ketones.

How can you do the following conversion?

(i) Butyne to Butan-2-one
(ii) Butene to Ethanal
SOLUTION

(i) CH3 − C ≡ C − CH3 

(i) dil H2SO4
HgSO4
→ CH3CH2 − CO − CH3

(i)O3
(ii) CH3CH
= CH − CH3 →
(ii) Zn/H2O
2CH3 − CHO

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Aldehydes, Ketones and Carboxylic acids

12.4.4 CHEMICAL PROPERTIES

1. Nucleophilic Addition Reactions
-
Nu
The carbon acts as an electrophilic
center and acts as a site of attack R Nu
-
for the nucleophile. The hybridisation O O
R
changes from sp2 to sp3; this also leads R
R
to the change from a trigonal planar
structure to tetrahedral. sp²
(Trigonal planar)
sp³
(Tetrahedral)

Generally, aldehydes are more reactive than ketones.

There are two prime reasons for this:
‹ Presence of the two bulky groups attached to the
carbonyl centers leads to a hindrance in the attack.
‹ The alkyl groups also reduce the electrophilicity of
the carbonyl carbon.

Addition of hydrogen cyanide (AIPMT 2003, 2006)


Nucleophilic addition of HCN on carbonyl group gives cyanohydrin.
–
δ+ δ– O CN
– H+
C O : CN C C
CN OH
Cyanohydrin
Tetrahedral
intermediate

Addition of sodium hydrogensulphite

Aldehydes and ketones give water-soluble bisulphite addition product when
treated with sodium bisulphite.
OSO2H proton transfer OSO2Na
C O NaHSO3 C C
ONa OH
Bisulphite addition
compound
(crystalline)

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 Chemistry

Addition of Grignard reagent (AIPMT 1989)


Grignard reagent gives sec. alcohol and tert. alcohol with aldehydes (except
formaldehyde) and ketones, respectively.

C O Mg–X H 2O
C O R Mg – X C OH Mg(OH)X
R R
Adduct

Addition of ammonia/ammonia derivatives (AIPMT 2000, 2005)


Acid catalysed nucleophilic addition of ammonia, and its derivatives on
aldehydes and ketones gives C = N – Z as the final product

OH
C O H2N – Z C C N–Z H2O
NHZ

Z Reagent name Carbonyl derivative Product name

–H Ammonia C = NH Imine

Substituted imine
–R Amine C = NR
(Schiff’s base)

—OH Hydroxylamine C = N– OH Oxime

—NH2 Hydrazine C = N– NH2 Hydrazone

HN Phenylhydrazine C=N-NH Phenylhydrazone

O2N O2N
2,4-Dinitrophenyl- 2,4-Dinitrophenyl
HN NO2 hydrazine C=N-NH NO2 hydrazone

O O
Semicarbazide C=N-NH C NH2 Semicarbazone
NH C NH2

Table 12.4.1 Some N-Substituted Derivatives of Aldehydes and Ketones (>C=N–Z)

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Aldehydes, Ketones and Carboxylic acids

Addition of alcohols
Aldehyde and ketones with dihydric alcohol gives hemiacetals and hemiketals
respectively, which on further treatment with monohydric alcohol converts to
acetals and ketals, respectively.
R CH2OH HCl gas R O CH2
C O C H2 O
R CH2OH dil. HCl
R O CH2
Ethylene glycol ketal

ROH OR OR

HCl gas ROH
R–CHO R–CH R–CH H 2O
H+
OH OR

Hemiacetal Acetal

2. Reduction
Reduction to alcohols
Aldehydes and ketones are reduced by NaBH4 or LiAlH4 to give primary and
secondary alcohols, respectively.
NaBH4
RCOR′ LiAlH4
R–CH–R′

Reduction to hydrocarbons
(i) Reduction of C = O group by hydrazine followed by heating with KOH in

ethylene glycol is wolff-kishner reduction. (AIPMT 2007, 2011, 2012)

NH2NH2 KOH/ethylene glycol
C O –H2O
C NNH2 heat
CH2 N2

(ii) Zinc-amalgam and conc. HCl converts C = O group into CH 2 group.


(Clemmensen reduction)
Zn-Hg
C=O CH2 H 2O
HCl

3. Oxidation
Aldehydes oxidise to carboxylic acid yielding only one carboxylic acid per molecule, whereas oxidation
of ketones leads to the formation of two carboxylic acids per molecule due to C-C bond cleavage.
[O]
R-CHO  → R-COOH

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 Chemistry

TRAIN YOUR BRAIN

Question: You are given four chemicals: ethanal, ethanol,
2-pentanone and formaldehyde. Which of these will give a
positive test for Iodoform test? (AIPMT 1998)
Sol. We only need to see which of the following has a methyl
ketone group present. The Presence of this group will make
it certain that the compound will give a positive iodoform test.
‹ Ethanol on oxidation gives acetaldehyde which is having
methyl carbonyl ketone, and it gives a positive Iodoform
test.
‹ Ethanal: Contains a methyl ketone group.
‹ 2-pentanone: Contains a methyl ketone group.
‹ Formaldehyde: Contains carbonyl group, but methyl group
is absent.
Thus, ethanol, ethanal and 2-pentanone will give a positive
iodoform test.

As the aldehydes are easily oxidisable as compared to ketones, mild

oxidising agents are employed as a test for distinguishing the aldehydes
from ketones.
1. Tollen’s Test: When aldehyde is treated with freshly prepared

ammoniacal silver nitrate solution (Tollen’s reagent), a bright silver
mirror forms at the side of the test tube. This test comes out to be
negative with ketones. (AIPMT 1994, 2001, NEET 2017)

RCHO + 2 [Ag(NH3 )2 ]+ + 3 OH- 
→ RCOO- + 2Ag + 2 H2O + 4 NH3
NCERT
2. Fehling’s Test: When aqueous copper sulphate (Fehling solution A) Highlights

and alkaline sodium potassium tartrate (Fehling solution B) are mixed in
equal amounts, Fehling’s solution is formed. Upon heating an aldehyde
with Fehling’s reagent, red-brown ppt is formed. (AIPMT 2012)

RCHO + 2 Cu2+ + 5 OH- 
→ RCOO- + Cu2O + 2 H2O
3. Haloform Test: Ethanal and ketones that have a methyl group attached

to the carbonyl carbon give a positive result for this test.
O O
NaOX
R C CH3 C ONa CHX3 (X = Cl, Br, I)

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Aldehydes, Ketones and Carboxylic acids

4. Reactions due to α-hydrogen

The α-hydrogen being acidic in nature gets deprotonated by the base.
O O O

C C C C C C

H B
Aldol Condensation (AIPMT 2007, 2008)

In the presence of dilute NaOH, aldehydes form β-hydroxy aldehydes (aldols), and ketones
form β-hydroxy ketones (ketols).
dil. NaOH
2 CH3–CHO CH3–CH–CH2–CHO –H2O
CH3–CH=CH–CHO
Ethanal But-2-enal
OH
(Aldol condensation
3–Hydroxybutanal product)
(Aldol)
CH3 CH3
Ba(OH)2
2CH3–CO–CH3 CH3–C–CH2CO–CH3 CH3–C=CH–CO–CH3
–H2O
Propanone
OH
(Ketol) 4-Methylpent-3-en-2-one
4-Hydroxy-4-methylpentan-2-one (Aldol condensation product)

The α, β-unsaturated carbonyl compounds are formed as a result of the ability of the aldols
and ketols to readily lose water.
Cross aldol condensation (NEET 2020)

When the starting materials are two different aldehydes and/or ketones, several products are formed.
Take, for example, a reaction in which ethanal and propanone are used as a starting material.
OH O

CH3 CH CH2 C H

+
OH O
O
CH3 C CH2 C CH3
CH3 C H
CH3
Dilute NaOH or KOH +
+

O OH O
CH3 C CH3 CH3 CH CH2 C CH3

OH O
CH3 CH CH2 C H

CH3

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 Chemistry

5. Cannizzaro Reaction (AIPMT 2007)

For the carbonyl compounds which do not possess α-hydrogen, disproportionate on heating
with conc. alkali.

2 CHO + Conc. NaOH CH2OH COONa

Benzaldehyde Benzyl alcohol Sodium benzoate

6. Electrophilic Substitution reaction

The resonating structures of benzaldehyde show that the carbonyl group acts as -meta directing
in nature. This leads to ease of electrophilic substitution at the -meta position.
- - -
H H O H O H O
C O C C C

+ +

Example: Benzaldehyde on nitration gives meta-nitro benzaldehyde.

O2N

CHO CHO

Benzaldehyde m-Nitrobenzaldehyde

What is the increasing order of reactivity of the

following towards HCN addition?
(a) PhCOCH3 < CH3COCH3 < HCHO
(b) PhCOCH3 < HCHO < CH3COCH3
(c) HCHO < CH3COCH3 < PhCOCH3
SOLUTION

(d) HCHO < PhCOCH3 < CH3COCH3

Option (a) is correct.

The addition of HCN is nucleophilic addition. Greater the electron deficiency
of the carbonyl group higher the rate of reaction.
Hence,
HCHO > CH3COCH3 > PhCOCH3 is the correct order.

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Aldehydes, Ketones and Carboxylic acids

12.5 CARBOXYLIC ACIDS

The compounds containing one carboxy acid (-COOH) group are identified as carboxylic acids.
Carboxylic acids with higher aliphatic chains (C12-C18) are known as fatty acids that naturally
occur in fats.

12.5.1 COMMON CARBOXYLIC ACIDS

O

O OH
O

HO OH

H OH
H 3C OH
C
Acetic
HO O acid O O
Formic acid (Vinegar) Adipic acid phthalic acid

Sodium benzoate is a common food preservative. Ethanoic acid is used to prepare vinegar
(4-8% aqueous solution). Esters derived from benzoic acid are used as perfumes.

12.5.2 STRUCTURE OF CARBOXYL GROUP

The electrophilicity of the carbonyl carbon in carboxylic acid is less than that of carbonyl carbon
of aldehyde and ketones because of the resonance.

O O O
O C C
O H O H O H
+

12.5.3 PREPARATION OF CARBOXYLIC ACIDS

From primary alcohols and aldehydes

Oxidation of primary alcohols and aldehydes using potassium permanganate in a

neutral, acidic or alkaline media CrO3-H2SO4 (Jones reagent) gives carboxylic acid.

CrO3–H2SO4
CH3(CH2)8CH2OH CH3(CH2)8COOH
1-Decanol Decanoic acid

13
 Chemistry

From alkyl benzenes

Aromatic carboxylic acids can be prepared using aromatic alkanes by vigorous
oxidation with chromic acid or acidic or alkaline KMnO4.
CH3 COOK COOH
KMnO4–KOH H3O+
Heat

Benzoic Acid

NCERT
Oxidation of alkylbenzene containing tertiary carbon does not take place. Highlights

From nitriles and amides

Hydrolysis of nitriles to carboxylic acid takes place in the presence of acidic or
basic catalyst.
H3O
CH3CONH2 ∆
CH3COOH NH3
Ethanamide Ethanoic acid
+
H3 O
CH3 CN ∆
→ CH3 COOH + NH3

From Grignard’s reagents

The reaction of CO2 (dry ice) with Grignard’s reagents and then a subsequent
hydrolysis leads to the formation of carboxylic acid.
O
Dry ether H3O+
R–Mg–X O=C=O R C RCOOH
– +
O MgX

The method employed to prepare carboxylic acid using

Grignard’s reagent and nitriles actually uses alkyl halides as
the starting material and hence adds up one more carbon
to the alkyl halides. This is called “ascent of the series”.

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Aldehydes, Ketones and Carboxylic acids

From acyl halides and anhydrides

Anhydrides and acyl chlorides get hydrolysed to form carboxylic acids.

H2
C COOH
H3C C
O O H2
H / H2O
⊕
+
H3C
H2
C O C3H7 C
H2
H3C COOH

From esters
Hydrolysis of esters leads to the formation of carboxylic acid.(AIPMT 1996, 2015)

COOC2H5 COOH
H3O+
C2H5OH

Ethyl benzoate Benzoic acid

Which of the following methods results in the

synthesis of carboxylic acids?
(a) Substitution reaction of the carbonyl compound
with NaCN
(b) Reduction of alcohols and aldehydes
(c) Carbonation of organometallic reagents
SOLUTION

(d) None of the above

Carbonation of organometallic reagents:

CO2 O O
HO
R MgBr C C
R OMgBr - MgBrOH R OH

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 Chemistry

12.5.4 PHYSICAL PROPERTIES

1 2 3 4

Carboxylic acids Carboxylic acid Aliphatic carboxylic As the length of

upto nine carbon exists as a dimer in acids (only upto 4 the alkyl chain
atoms are liquids, the vapour phase. carbon atoms) are increases, the smell
whereas higher soluble in water due of the compound
carboxylic acids to H-bonding. changes from foul
are practically to pleasant.
solids, just like
hydrocarbons.

(NEET 2018)

TRAIN YOUR BRAIN

Question: Carboxylic acids generally have a higher boiling point
when compared to corresponding aldehydes. Can you think of a
valid reason for this?
Sol. Carboxylic acids have the tendency to form an “intermolecular
hydrogen bond”, which results in an increase in the boiling point.
Carboxylic acid, in fact, prefers to stay in a dimeric vapour phase
as well as in an aprotic solvent.
O H O

R C C R

O H O

12.5.5 CHEMICAL REACTIONS

1. Acidity (Cleavage of O-H bond)
Carboxylic acids dissociate in water to give resonance stabilised carboxylate anions and the
hydronium ion. The conjugate base here is the carboxylate ion which is resonance stabilised,
and hence in aqueous solutions, carboxylic acid gets easily converted to carboxylates and
prefers to remain in this state. This reason is accredited to the higher acidity of carboxylic
acids (higher than phenols and alcohols also). (AIPMT 2003, 2007, NEET 2012, 2016)

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Aldehydes, Ketones and Carboxylic acids

Carboxylic acids also react with metals and alkalies, where they behave NCERT
as strong acids and therefore react with carbonates to release CO2 and Highlights

water. This is used as a test to confirm the presence of carboxyl groups.

O O O O
R C H2O H3O+ R C R C R C
OH O O O

The electron donating group (EDG) destabilises the anion, whereas the electron-withdrawing
group (EWG) stabilises the anion. Therefore, we can conclude that the EDG groups increase
the pKa and EWG groups decreases the pKa.

O O

EDG C EWG C

O O

Direct attachment of an sp2 hybridised carbon to the carboxylate anion leads to an increase
in acidity due to the electronegative character of an sp2 hybridised carbon.

Beyond NCERT
Ortho Effect
O OH O OH

CH3 steric CH3

hinderance

Due to the presence of the methyl substituent at the ortho- position, the carboxylic acid
group, which would undergo resonance in normal circumstances, changes its plane with
respect to that of the phenyl ring. This does not allow for the resonance to take place and
hence increases the acidity of the carboxylic acid. This makes it much more acidic than
the meta- and para- counterparts.

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 Chemistry

2. Cleavage of C-OH bond

Formation of acetic anhydride

O O OO
H,∆
+

H3C C C CH3 or P2O5, ∆ CH3 C C CH3

OH HO O
Ethanoic acid Ethanoic anhydride

Reactions with PCl5, PCl3 and SOCl2

In the given reactions with different reagents, SOCl2 is preferred over others as
SO2 and HCl are formed and are gaseous. (AIPMT 2005)


RCOOH PCl5 RCOCl POCl3 HCl
3RCOOH PCl3 3RCOCl H3PO3
RCOOH SOCl2 RCOCl SO2 ↑ HCl ↑

These reactions are similar to what we saw for alcohols.

Reaction with ammonia (NEET 2019)


COOH COONH4 CONH2
∆
NH3 –H2O

Ammonium benzoate Benzamide

Esterification Reaction (Nucleophilic Acyl Substitution)

:

This reaction involves the breaking of -C-OH bond via the water removal.
+
O OH OH
H+ R′–OH
R C R C R C O R
OH OH OH H
Tetrahedral intermediate NCERT
Carboxylic acid Highlights
Proton
transfer

+
O OH OH
–HOH
R C R C R C O R′
O–R′ O–R′ OH2
Ester Protonated ester

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Aldehydes, Ketones and Carboxylic acids

3. Reactions involving -COOH group

Reduction Decarboxylation

Sodium salts of carboxylic acids when

Reduction of carboxylic acids yields
heated with soda-lime loses CO2 to give
primary alcohols.
(i)LiAlH /ether or B H
hydrocarbon.
R − COOH 
4
+
2 6
→ R − CH2OH NaOH & CaO
(ii) H 3O R − COONa 
Heat
→ R − H + Na2CO3
(AIPMT 2000)
(AIPMT 1992)

4. Substitution Reactions

Hell-Volhard-Zelinsky Reaction (Halogenation)

This reaction is only possible with the carboxylic acid containing α-hydrogen. where
Cl2 or Br2 with red phosphorous followed by hydrolysis produces -Halo carboxylic

a
acid. (AIPMT 2009)

(i) X2/Red phosphorus
R–CH2–COOH R–CH–COOH
(ii) H2O

X
X = Cl, Br
α – Halocarboxylic acid

Ring Substitution
Aromatic carboxylic acids via electrophilic ring substitution gives meta substituted
product.
COOH COOH

Br2/FeBr3

Br
m-Bromobenzoic acid

Aromatic carboxylic acids fail to undergo Friedel Crafts reaction as the

NCERT
–COOH group is a deactivating group. AlCl3 acts as Lewis acid and Highlights
reacts with the oxygen bonded with carbonyl carbon of the carboxyl
group making the overall reaction less effective.

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 Chemistry

The correct order of decreasing acid strength

of trichloroacetic acid (A), trifluoroacetic acid
(B), acetic acid (C) and formic acid (D) is
(a) B > A > D > C (b) B > D > C > A
SOLUTION

(c) A > B > C > D (d) A > C > B > D

Option (a) is the correct
As –I effect increases, –COOH group becomes more electron-deficient and the
tendency to lose H+ ions increases, i.e., acid strength increases. As +I effect
increases, acid strength decreases.
Thus, the correct order of acid strength is
CF3COOH > CCl3COOH > HCOOH > CH3COOH
(B) (A) (D) (C)



TRAIN YOUR BRAIN
Question:
Which one of the following compounds will react with NaHCO3
solution to give sodium salt and carbon dioxide?
(a) Acetic acid
(b) n-Hexanol
(c) Phenol
(d) Both (b) and (c)
Solution: (a)
Only acetic acid is more acidic than carbonic acid (conjugate acid
of NaHCO3); hence it dissolves in NaHCO3,
CH3COOH + NaHCO3 → CH3COONa + H2CO3(CO2 + H2O)
Stronger acid Weaker acid

while phenol and n-hexanol are less acidic than carbonic acid,
and hence they do not react with NaHCO3.

20
 LEVEL - II
Aldehydes, Ketones &Carboxylic acids
Introduction
A carbonyl group is a functional group that comprises carbon atom double-bonded to an oxygen atom
(C = O). Compounds that have the carbonyl group are called carbonyl compounds. In aldehydes, the
carbonyl group is attached to a C and H while in ketones, it is bonded to two C atoms. The general
formulae of these compounds are given below:
R R
C=O C=O
H R'
Aldehyde Ketone

Polarity and Boiling Point of Carbonyl Compounds:

The (C = O) bond is polarised due to high EN of O atom relative to C atom, as shown below:
..
C=O . .: C–O . . : (Dipolar ion)
Thus the C atom acts as electrophile (Lewis acid) and O atom as nucleophile (Lewis base). Therefore,
carbonyl compounds have some dipole moment and are more polar than ether.
There is an interaction among bond dipoles. These interactions are called as dipole-dipole interaction
and due to these interactions molecules are held quite strongly.

C–O C–O

Comparison of Polarities of (C = O) and (C = C) Bonds:

The (C = C) group has no significant polar character, but (C = O) group has polar character since O
atom is more electronegative than C atom. Further, (C = O) group is polarised with C + and O–, in
−
which O acts as nucleophilic site and C+ acts as electrophilic site. On the contrary, the -bond of (C
= C) bond in an source and acts as nucleophilic site.

Test of Carbonyl Compounds:

Both aldehydes and ketones give coloured precipitates with 2, 4-DNP (Brady’s reagent). Positive DNP
test shows the presence of (C = O) group. Aldehydes are distinguished from ketones with Tollens or
Fehling’s or Benedict’s or Schiff’s reagent.

Preparation of Aldehydes and Ketones:

1. By Oxidation of Alcohols: 1° and 2° alcohols on oxidation under different conditions give aldehydes
and ketones, respectively.
1° alcohols are easily oxidised first to aldehydes and then to acids, 2° alcohols are easily oxidised
to ketones, and 3° alcohols are difficult to oxidise

2. By Dehydrogenation of Alcohols: This method is suitable for volatile alcohols. Alcohol vapours are
passed over heavy metal catalysts (Ag or Cu). 1°, 2° and 3° alcohols give aldehydes, ketones and
alkenes, respectively.

21
3. From Hydrocarbons:
(i) By Ozonolysis of Alkenes: ozonolysis of alkenes followed by reduction with (Zn dust + acetic
acid) gives aldehydes or ketones or a mixture of both depending on the substitution pattern of
alkene.
(ii) By Catalytic Hydration of Alkynes: Addition of dil. H2SO4 in the presence of HgSO4 to alkyne
gives aldehydes or ketones, depending on the nature of alkyne. Ethyne or acetylene gives
acetaldehyde, while propyne gives acetone.

4. Partial Oxidation of Alkyl Benzene (Etard Reaction):

Toluene Benzaldehyde
5. By Side-Chain Chlorination Followed by Hydrolysis:

6. Gattermann Aldehyde Reaction: Benzene or its derivative on reaction with HCN + HCl + AlCl3 gives
benzaldehyde or substituted benzaldehyde. Solid Zn(CN)2 is also used as an in situ source of HCN,
e.g.,
CH=NH2]Cl
CH = O
H2O
I. + H – C  N + HCl + AlCl3 → NH4Cl +
Imine hydrochloride
(Intermediate compound)
H2O
II. Me + HC  N + HCl + AlCl3 → Me CH=NH2]Cl Me CHO+NH4Cl
Toluene

7. Gattermann-Koch Aldehyde Synthesis: Benzene or its derivative on reaction with (CO + HCl + AlCl3
or CuCl) gives benzaldehyde or substituted benzaldehyde.
CH = O

+ CO + HCl + Anhyd. AlCl3 or CuCl →

8. Rosenmund Reduction:

i.

ii

22
9. Stephen Reduction (Partial Reduction of Nitriles):
Nitriles (alkyl cyanides) are partially reduced to corresponding imine with SnCl2 (stannous chloride)
in the presence of HCl, which on hydrolysis gives corresponding aldehyde. It does not reduce (C =
C) or (C  C) bond. This reaction is called Stephen reduction.

10. By Passing The Vapours of Fatty Acids Over Manganous Oxide (MnO) AT 573 K:
This method is analogous to the above method. Formic acid alone gives formaldehyde; other acids
give ketones. Two different acids give mixture of three compounds as in the above case, e.g.,

HCO OH + H COO H ⎯⎯⎯ → HCHO + CO2 + H2O

MnO
i. 

CH3CO OH + H COO H ⎯⎯⎯ → CH3CHO (Major) + HCHO (Minor) + CH3COCH3(Minor) + CO2 + H2O
MnO
ii. 

iii. CH3CO OH + H COO CH3 CH3COCH3 + CO2 + H2O.

Chemical Properties:
Nucleophilic Addition Reaction: Due to strong electronegativity of oxygen, the mobile  electrons pulled
strongly towards oxygen, leaving the carbon atom deficient of electrons. Carbon is thus readily attacked
by Nu. The negatively charged oxygen is attacked by electron deficient (electrophile) E +.

Reactivity  Magnitudeof  + vecharg e

of carbonyl g roup  − I effect
1

+I effect

Example:1 Arrange the following for reactivity in decreasing order

(a) (i) (ii) (iii)

(b) (i) ClCH2CHO (ii) NO2CH2CHO (iii) CH3CHO

(iv) CH3CH2CHO
(c) (i) CH3CHO (ii) ClCH2CHO (iii) HCCl2CHO (iv) CCl3CHO

(d) (i) (ii) (iii)

(iv)

Solution. (a) I > II > III (b) II > I > III > IV
(c) IV > III > II > I (d) IV > I > II > III

23
 CH3 – is +I group, decreases the intensity of +ve charge on C-atom of group.

Cl – is –I group increases the intensity of +ve charge on C-atom of group.

(1) Addition of HCN:

propanol

(2) Addition of NaHSO3: This reaction is utilized for the separation of carbonyl compounds from non-
carbonyl compounds.

(3) With Alcohol:

(4) Reaction with sodium alkynide:

(5) Reaction with Grignard reagent:

24
(6) Reaction with glycol:

(7) Reaction with H2O: It is a reversible reaction.

Note: Chloral (Cl3C – CH = O) forms stable hydrate [CCl3 – CH(OH)2 (chloral hydrate)]

(8) Reaction with Ammonia Derivatives: These are condensation or addition elimination reaction.
These proceeds well in weakly acidic medium.
NH3 ⎯→ NH2Z (Ammonia derivative)

Ammonia Derivatives (NH2Z):

–Z H2N–Z C=N–Z
1. –H H2N–H (NH3) C=NH (Imine)
Ammonia
2. –R H2N–R (P-amine) C=N–R
(Substituted Imine)
(Schiff's base)
3. –OH H2N–OH C=N–OH (oxime)
(Hydroxyl amine)
4. –NH2 H2N–NH2 (Hydrazine) C=N–NH2 (Hydrazone)
5. –NHPh H2N–N HPh C=N–NH–Ph
(Phenyl Hydrazine) (Phenyl Hydrazone)
6. NO2 O2N NO2

–NH NO2 H2N–NH NO2 C=N–NH NO2

2,4-Dinitrophenyl 2,4-Dinitrophenyl
Hydrazine (2,4- DNP) hydrazine
(Brady's Reagent) Red, orange, yellow ppt
(solid)
(Test of carbonyl comp.)

25
 7. O O O
–NH–C–NH2 H2N–NH–C–NH2 C=N–NH–C–NH2
(Semicarbazide)
(Semicarbazone)

Reaction with PCl5:

Aldehydes or ketones react with PCl5 to give gem-dihalides.
Cl
i. CH3CHO + PCl5 → CH3CH + POCl3
Cl
Ethylidene
chloride
Cl
ii. (CH3)2C = O + PCl5 → (CH3)2C + POCl3
Cl
2,2-Dichloropropane

Concept Builder-1

1. The increasing order of the rate of HCN addition to compounds a to d is:

(a) HCHO (b) CH3COCH3
(c) PhCOCH3 (d) PhCOPh
(1) a < b < c < d (2) d < b < c < a
(3) d < c < b < a (4) d < a < c < b

2. When two mole of alcohol reacts with 1 mole of ketone, it gives:-

(1) Hemiacetal (2) Acetal (3) Hemiketal (4) Ketal

3. The product 'P' in the following reaction is

O
||
NaHSO
H ⎯⎯⎯⎯→
3
(P)
SO3Na OSO2Na

(1) H , Non-crystalline (2) OH , Crystalline

OSO2Na SO3Na
(3) OH , Non-crystalline (4) OH , Crystalline

4. Which of the following will form stable hydrate ?

CO
(1) CCl3CHO (Chloral) (2) CO (Ninhydrin)
CO
(3) (CF3)2CO (4) All of these

H O
+ CH3MgBr ⎯⎯⎯→ (A)
3
5.
14

Product (A) is:

26
 O O
|| ||
(1) C–CH 3 (2) C–CH 3
14

O
||
(3) C–CH 3 (4) CH2–CHO
14 14

Aldol Condensation
Reactions Due to -H Atom: The aldehydes and ketones undergo a number of reactions due to the
acidic nature of -H, which in turn is due to the strong e -withdrawing effect of the (C = O) group and
resonance stabilisation of the conjugate base.

O O O
|| || |
OH
H3C – C – CH2 – H H3C – C – CH2 H3C – C = CH2

Base-Catalysed Aldol Condensation: When two molecules of the same aldehyde or ketone containing
-H atom condense together in the presence of dilute alkali, such as NaOH, KOH, K 2CO3, Na2CO3, or at
least 2 -H atom, to give a molecule of aldol or ketol (-hydroxy aldehyde or ketone), it is called aldol
reaction. On heating, it loses a molecule of H2O to give a molecule of , -unsaturated aldehyde or
ketone, it is called aldol condensation.

i.

ii.

Crossed Aldol Condensation:

It is the condensation taking place when two different aldehydes or two different ketones or one
aldehyde and one molecule of ketone both containing -H atoms. A number of products due to self-
condensation and cross condensation are obtained, for example,
O
||
i. CH3 – CH + CH2 – C – CH3 CH3 – CH – CH2 – COCH3
|| | |
O H OH
(1) (2) (Cross condensation)
Acetaldehyde Acetone (A)
CH3 CH3
| |
ii. CH3 – C ..... CH2 – CHO CH3 – C – CH2 – CHO
|| | |
O H (1) OH
(2)
Acetaldehyde (Cross condensation)
Acetone
(B)

27
iii. CH3 – CH....CH2 – CHO CH3 – CH – CH2 – CHO
|| | |
O H OH
(1) (1) (Self condensation)
Acetaldehyde Acetaldehyde (C)
CH3 CH3
| |
iv. CH3 – C ..... CH2COCH3 CH3 – C – CH2 – COCH3
|| | |
O H OH
(2) (2)
(Self condensation)
Acetone Acetone
(D)
The ease and percentage of formation: A > C > B > D (since reactivity of aldehydes is more than that
of ketones). In (A), ketones are better carbanion sources and aldehydes are good acceptors. In other
words, ketone carbanions are better nucleophiles than aldehyde carbanions.
Reverse Problem:
If the cyclised product of intra-molecular aldol condensation is given, for obtaining the starting
reactant, break ,  (C = C) bond by adding H2O, i.e., H2 at -C atom and O at -C atom, e.g.,
O O
|| ||
H2 (i) OH CH3
i. O (ii) or H
O
Me |
Me
Aldol product Starting reactant

ii.

iii.

Cannizzaro Reaction:
Two molecules of the same aldehyde lacking -H atom undergo disproportionation or redox reaction
in the presence of strong base to give a molecule of alcohol and a molecule of the salt of an acid, e.g.,
HCHO + HCHO ⎯⎯⎯→ H − CH2OH + HCOONa
NaOH
i.
Methanol Sod. formate

Ph – CHO + Ph – CHO ⎯⎯⎯ → Ph − CH OH + Ph − COOK

KOH
ii. 2
Benzyl alcohol Pot. benzoate

iii. 2Me3C – CHO ⎯⎯⎯→ Me3C – CH2OH + Me3C – COONa

NaOH

CHO ⎯⎯⎯→
NaOH
iv. 2 CH2OH + COONa
O O O
Furaldehyde

Mechanism :
[Takes place by (hydride ion transfer) when the concentration of the base is low.]

28
 Step 2
H H H Hydride ion H H
| Step 1
| | transfer
| |
OH C = O H–O–C–O C=O slow
HO – C = O + H – C – O
| (fast) | | |
(R.D.S.)
H H H H
[A ]
Step 3
H H
| |
Proton
exchange
H – C – OH + O – C = O
| Formate
H ion
Methyl
alcohol
Hence the Cannizzaro reaction is low concentration of a strong base is bimolecular with third-order

kinetics, second order w.r.t. aldehyde, and first-order w.r.t. OH ions.

Crossed Cannizzaro Reaction:

HCH = O + PhCH = O ⎯⎯⎯

OH
→HCOO + PhCH2OH
(I) (II)

( )(
More reactive Less reactive
than (II) than I )
  
 OH attack

at (I) 
 and H transferred 
 from adduct ion of (I) 
  CH3OH + PhCOO

Test to Distinguish Aldehyde and Ketone

Tollens, Fehling’s, Benedict’s, and Schiff’s Reagents
Aldehydes are easily oxidised to acids containing the same number of C atoms. Hence, they are oxidised
not only by strong O.A. such as KMnO4 and K2Cr2O7 but also by weak O.A. such as Br2 water, Ag+, Cu2+
ions, etc. As a result, aldehydes act as strong reducing agents. They reduce (i) Tollens reagent to
metallic silver (silver mirror), and (ii) Fehling’s or Benedict’s solution (F.S. or B.S.) to a red precipitate
of cuprous oxide (Cu2O).
(a) Reduction of Tollens reagent: T.R. is an ammoniacal solution of AgNO3, When an aldehyde is heated
with T.R., the latter is reduced to metallic Ag and aldehydes are oxidised to acids. Thus, T.R. is
called an oxidising agent.
AgNO3 + NH4OH ⎯→ AgOH + NH4NO3
Grey ppt.

AgOH + 2NH4OH ⎯→ [Ag(NH3)2]

Tollens reagent
RCHO + 2 [Ag(NH3)2] + 2 Ag  + 4 NH3 + 2H2O
Silver mirror
The silver, thus deposited, shines like a mirror. Hence, this test is known as silver mirror test. For
example,
RCH = CH – CHO ⎯⎯⎯ → RCH = CH – COOH
T.R.

29
(b) Reduction of Fehling’s solution: It is an alkaline solution of CuSO4 containing some Rochelle salt,
i.e., sodium potassium tartrate (NaOOC – CH (OH) – CH (OH)– COOK). When an aldehyde is heated
with F.S., the latter is reduced to give a red precipitate of cuprous oxide.

RCHO + 2Cu2+ + 5OH ⎯→ RCOO + Cu2O  3H2O
F.S.
Red ppt.
F.S. ‘A’ contains aqueous solution of CuSO4, while F.S. ‘B’ contains ammoniacal solution of Rochelle
salt. For testing aldehydes, F.S. A and B are mixed in equal amounts.
(c) Reduction of Benedict’s solution: It is an alkaline solution of CuSO4 containing some sodium citrate
(NaOOC – CH2 – C(OH) (COONa) – CH2COONa). It reacts in the same way as Fehling’s solution.
(d) Reduction of Schiff’s reagent: It is dilute solution of rosanaline hydrochloride in H 2O, whose red
(magenta) colour has been discharged by passing SO2. When this reagent is added to aldehyde,
magenta colour is restored.
1. All Aldehydes give positive test with these reagents.
2. Aromatic aldehyde doesn’t give positive test with Fehling solution and benedict’s solution
3. Tollens reagent test is also given by  hydroxy ketones (like fructose)
4. Formic acid also give positive test with these reagent.

Concept Builder-2

1. In the Cannizzaro reaction

OH–
2PhCHO ⎯⎯⎯→ PhCH2OH + PHCOO–
the slowest step is:
(1) The attack of OH– at the carbonyl group
(2) The transfer of hydride to the carbonyl group
(3) The abstraction of proton from the carboxylic acid
(4) The deprotonation of PhCH2OH

CHO
2. ⎯⎯⎯⎯⎯⎯
(i) conc. NaOH
→ ?
(ii) H O/H+ / 
CHO 2

COOH COOH CH2OH

(1) (2) (3) (4)
COOH CH2OH CHO
3. An aromatic compound ‘X’ with molecular formula C9H10O gives the following chemical tests:-
(i) Forms 2, 4-DNP derivative
(ii) Reduce Tollens reagent
(iii) Undergoes Cannizzaro reaction and
(iv) On vigorous oxidation, 1, 2-benzenedi-carboxylic acid is obtained
The compound
CHO CHO
C2H5 CHO
(1) (2) (3) (4)
C2H5
C2H5
4. Fehling’s solution can make distinction between:
(1) MeCHO and PhCHO (2) MeCHO and

30
 (3) MeCHO and HCHO (4) All of these
5. The diketone

on intramolecular aldol condensation gives the final product:

O O O O
OH
(1) (2) (3) (4)
CH3 CH3 CH3
Carboxylic Acid

31
Alkanoyl halide (Acyl halide)

Reactions of ester

32
Acid anhydrides

Acid amide (alkanamide)

Concept Builder-3

(1) Br /P NH
1. CH3CH2COOH ⎯⎯⎯⎯⎯ 2
(2) H O
→ A ⎯⎯⎯→
3
Y.
2

The product Y is :
(1) Lactic acid (2) n-propyl amine (3) Ethylamine (4) Alanine

2. Carboxylic acid group can be detected by :

(1) Sodium bisulphite test (2) Fehling’s solution test
(3) Tollen’s reagent (4) With NaHCO3

33
 
3. CH3COOH ⎯⎯⎯
PO
→ X. Identify X
2 5

(1) CH3COCH3 (2) CH3CHO (3) (CH3CO)2O (4) CH4

4. Identify Z in the sequence

 +
H2 O(H )
CH3COONH4 ⎯⎯⎯
Heat
→ Y ⎯⎯⎯⎯ → Z:
(1) CH3CH2CONH2 (2) CH3CN (3) CH3COOH (4) (CH3CO)2O

ANSWER KEY

Concept Builder (1)

1. (3) 2. (4) 3. (4) 4. (4) 5. (3)

Concept Builder (2)

1. (2) 2. (3) 3. (1) 4. (1) 5. (3)

Concept Builder (3)

1. (4) 2. (4) 3. (3) 4. (3)

34
 Exercise-I
1. Which of the following forces is correctly 5. Cannizzaro reaction does not take place
described about boiling point of Aldehydes
with:
& ketones :
(1) Hydrogen bond (1) (CH3)3CCHO
(2) Vander wall force
(3) Dipole-dipole attraction (2) CH O
(4) None of these

2. In Cannizzaro reaction :
(3) CHO
(1) Aldehyde is converted into alcohol
(2) Alcohol is converted into aldehyde
(4) CH3CHO
(3) Primary amine is converted into isocyanide
(4) Acid is converted into amine
6. Predict the product when given compound
–
OH
3. CH3–CHO ⎯⎯⎯→ CH3CH(OH)CH2CHO reacts with LiAlH4 :
In the aldol condensation of acetaldehyde
represented above, which of the following
intermediate species are obtained ?
O
(1) CH 2=C–H
O
(2) : CH2 –C–H
(1)
O O
(3) CH3 –C–CH2 –C–H
H
(4) All of the above

(2)
4. Which of the following is an example of
aldol reaction ?
(1)C6H5CHO+HCHO C6H5–CH2–CH2–OH

(3)
(2) CH3–CH=O

O OH
NaOH
(3) H–C–H H–C–O¯Na++CH3OH


(4)
(4)

C2H5O¯Na+

35
7. Predict the product when given compound 10. Which factors will increase the reactivity of
reacts with NaBH4. C = O group?
(i) Presence of a group with positive
inductive effect
(ii) Presence of a group with (–ve)
inductive effect
(iii) Acidic medium
(1) Only (i) (2) Only (ii)
(1) (3) Both (i) & (iii) (4) Both (ii) & (iii)

11.

(2) The products (A) and (B) are :

(1)

(3)
(2)

(3)
(4)

(4)
8. In the following reaction product P is
O
⎯⎯⎯⎯ H2
⎯→P
R – C – Cl Pd-BaSO4

(1) RCH2OH (2) RCOOH H O+

12. (CH3 )2 CO ⎯⎯⎯⎯
NaCN
(HCl)
→ A ⎯⎯⎯
3
⎯
→B
(3) RCHO (4) RCH3
In the above sequence of reactions A and
B are:
9. (1) (CH3)2C(OH)CN, (CH3)2C(OH)COOH
(2) (CH3)2C(OH)CNH2, (CH3)2C(OH)2
(3) (CH3)2C(OH)CN, (CH3)2CHCOOH
(4) (CH3)2C(OH)CNH2, (CH3)2C = O
The reagents (A), (B), and (C) are :
O
(1) in all cases
13.
(–)
OH
CHO + 'X' 293K
CH = CH – C

Identify ‘X’ :
(2) in all cases
(1) CH2 – CHO
(3) in all cases
(2) CH2 – CH2 – OH
(4) A  ,B , O
(3) C – CH3
C
(4) CH = CH3

36
14. Acetic acid exists as dimer in C6H6 due to: 20. Which of the following compound has the
(1) Condensation reaction largest equilibrium constant for the
(2) Hydrogen bonding
addition of water ?
(3) Presence of a carboxyl group
O
(4) Presence of hydrogen at -carbon ||
(1) CH3O C
15. The Hell-Volhard Zelinsky reaction is used
O
for preparing a/an : ||
(1) -Haloacid (2) -Haloacid (2) O2N C NO2
(3) Acid halide (4) -Haloacid
O
||
Alc.KOH (3) C–Ph
→ (A) ⎯⎯⎯⎯→ (B)
Cl2
16. CH3CH2COOH ⎯⎯⎯
red P

The compound (B) is : O

||
(1) CH3CH2OH (4) CH3O C NO2
(2) CH3CH2COCl
(3) CH2=CHCOOH
(4) CH3–CHCl–COOH Br
21. ⎯⎯⎯⎯
CH3MgBr
→ (A)
1 (eq.)
17. In esterification CH=O
(1) –OH of acid is replaced by C6H5OH
(2) H+ of acid is replaced by alkyl group (1) (2) O
O
(3) – OH of alcohol is replaced by chlorine
(4) – OH of acid is replaced by RO– group CH3

O
COOH (3) CH3 (4)
18. ⎯⎯⎯
NH3
→ A. Identify ‘A’ O CH3

COOH
(1) Benzene (2) Phthalimide 22. Which of the following will be the product
(3) Benzamide (4) Acetaldehyde of following reactions ?
CH3
19. In a set of reactions acetic acid yielded a |
product D. O + HO – CH2 − C − CH2 − OH ⎯⎯⎯
acid
→
|
CH3COOH ⎯⎯⎯→ A ⎯⎯⎯⎯⎯ →B ⎯⎯⎯ →
SOCl2 benzene HCN
anhy.AlCl3
CH3
(excess)

C ⎯⎯⎯
HOH
→D O O
The structure of D would be (1) (2)
O O
O O
(1) (3) (4)
O O

(2) 23. An organic compound C3H6O does not give

a precipitate with 2,4-dinitrophenyl
hydrazine reagent also does not react with
(3) metallic sodium. It could be :
(1) CH3–CH2–CHO
(2) CH3=CH–OCH3
(4) (3) CH3–COCH3
(4) CH2=CH–CH2–OH

37
 OH 27. The amino ketone shown below undergoes a
spontaneous cyclization on standing. What is
OH ⎯⎯⎯⎯⎯
PCC(excess)
→
24. (A)
the major product of this intramolecular
OH reaction?
OH
→ (C) ⎯⎯⎯→ (D)
NaBH4 O
1 equivalent
H
+ (B) ⎯⎯⎯⎯
CH3MgBr
+
||
H3O CCH3
Product (D) will be :
CH2CHNH2
OH OH
OH
CH–CH3 CH3
(1) (2) OH
O CH3
||
OH OH N
OH (1) (2)
(3) OH (4) CH3 CH3
CH3 CH3
N
25. Rank the following in order of increasing (3) (4)
NH2 CH3
value of the equilibrium constant for
hydration, Khyd. (smallest value first) :
O 28. End product (C) of the reaction is:
1. 2. O O O
|| || HO OH
+ (A) ⎯⎯⎯⎯⎯
2PhMgBr
→
OEt H
O 
|| (B) ⎯⎯⎯→
H3O
(C)
3. (CH3 )3 CCC(CH3 )3 O
|| Ph Ph O OH
(1) 1 < 2 < 3 (2) 3 < 1 < 2 (1) (2) || Ph
(3) 2 < 1 < 3 (4) 2 < 3 < 1 OH Ph
OH O
(3) || (4) OH O
26. Consider the following sequence of ||
OEt
Ph Ph
reactions :
Ketone A ⎯⎯⎯⎯⎯ → B ⎯⎯⎯⎯⎯ → C
1. C2H5MgBr H2 SO 4 , heat
2. H2 O − H2 O 29. Acetaldehyde reacts with semi carbazide,
H product will be:
⎯⎯⎯→ 1. O3
|| + (1) CH3CH = NNH – CO – NH2
2. Zn, H2 O
O O
(2) CH3CH = NCONHNH2
The ketone (A) is :
(3) CH3CH = NHNH2
(1) || O
O ||
(4) CH3 – C– NH – CONH2
(2) ||
O

(3) || 30. Cyanohydrin of the following compound on

O hydrolysis gives compound that can show
(4) || optical isomerism:
O
(1) HCHO (2) CH3CHO
(3) CH3COCH3 (4) All the above

38
31. The reagent most suitable for converting a 37. Which of the following products is formed
primary alcohol into an aldehyde is: in good yield by the reduction of methyl-
(1) K2Cr2O7 and H2SO4 4-oxo-hexanoate (A) with NaBH4?
(2) KMnO4 and NaOH

(3) , ClCrO3–, CH2Cl2

(1) Methyl-4-hydroxyhexanoate
(4) HNO3
(2) 6-Hydroxy-3-hexanone
(3) 1,4-Hexanediol
32. Stephen reaction is the reaction involving:
(4) 4-Hydroxyhexanal
(1) Reduction of alkanoyl chloride with
Pd/BaSO4. 38.
(2) Reduction of alkyl isocyanide with
sodium and alcohol.
Which statement(s) is/are correct?
(3) Reduction of alkyl cyanide with SnCl2
(1) The compounds (A) and (C) are
and HCl and hydrolysing the
and ,
intermediate aldimine.
respectively.
(4) Reduction of carbonyl compound with (2) The compounds (A) and (B) are
zinc amalgam and HCl and ,
respectively.
33. Acetone gives test with : (3) The compounds (C) and (B) are
(1) 2,4 Dinitro phenyl hydrazine and ,
(2) Fehling solution respectively.
(3) Schiff’s reagent (4) The compounds (B) and (C) are
(4) All
.
39. The reaction
34. Which is most difficult to oxidise :
CHO heat
(1) HCHO (2) CH3CHO + conc. NaOH ⎯⎯⎯ ⎯
→
CHO
(3) CH3COCH3 (4) CH3CH2CHO
produces
CH (OH)2
35. Aldehydes and ketones can be reduced to
(1) (2) O
corresponding hydrocarbons by : CH(OH)2
CH 2OH COO –
(1) Refluxing with strong acids
(3) –
(4) –
(2) Passing the vapours over SeO2 CO O COO

(3) Refluxing with zinc amalgam

40. Consider the following sequence of
(4) Refluxing with strong base
reactions.
NaOH LiAlH
36. Which of the following can be used to CH3COCH3 ⎯⎯⎯⎯
heat
→ A ⎯⎯⎯⎯
4
→B

differentiate between ethanal and The final product (B) is :

propanal- (1) (CH3)2C(OH)CH2COCH3
(1) Ammoniacal AgNO3 (2) (CH3)2C=CHCOCH3
(3) (CH3)2CHCH2CHOHCH3
(2) NaHSO3
(4) (CH3)2C=CHCHOHCH3
(3) I2 in presence of base
(4) 2,4-DNP

39
 Heat NH
46. In a reaction, (A) ⎯⎯⎯
3
→ (B) ⎯⎯⎯→ (C)
41. Major; product PO
⎯⎯⎯
2 5
→ C2H5CN (A), (B) and (C) are :
(1) CH3COOH, CH3COONH4 and CH3CONH2
(A) is : (2) CH3COCl, CH3CONH2 and CH3COONH4
(3) C2H5COOH, C2H5COONH4 and C2H5CONH2
(4) C2H5CONH4, C2H5CONH2 and C2H5COOH
(1) (2)

47. Let us consider an esterification of

isotopically labelled carboxylic acid :

(3) (4) 18
H+
+ CH3 + CH2OH ⎯⎯⎯
→ (X) and
(Y),
(X) and (Y) respectively are :

42. + R ⎯→ Aspirin ; R is
(1) ; H2O

(1) CH3 – OH (2) C6H5 – OH (2)

(3) CH3 – COCl (4) C6H5COCl (3) ; H2 O

(4) both (1) and (2)

48. The rate of esterfication of HCOOH (I),

43. + Carbolic acid ⎯→ CH3COOH (II), (CH3)2CHCOOH (III) and
(CH3)3CCOOH (IV) with ethanol follows in
The above reaction is the order :
(1) Friedel craft reaction (1) IV > III > II > I (2) I > II > III > IV
(2) Schotten Baumann reaction (3) II > I > IV > III (4) III > IV > I > II
(3) Benzoylation
(4) 2 & 3 both 49. Ethanol on heating with acetic acid in the
presence of a few drops of sulphuric acid
gives:
NH3  PCl5
44. ⎯⎯⎯ → X ⎯⎯ → Y ⎯⎯⎯ → Z; (1) Oil of wintergreen
Z is (2) Oil of mustard
(3) Fruity smell
(1) CH3 – CN (2) (4) Oil of bitter almonds

(3) CH3 – CCl3 (4) 50. By which of the following sequence of

steps can the alcohol RCH2CH2OH(X) be
converted into RCH2CH2COOH(Y)?
PBr
KCN H O+
45. Esterification is fastest in case of : (1) X ⎯⎯⎯
3
→ ⎯⎯⎯ → ⎯⎯⎯→
3
Y
(1) CH3COOH (2) HCOOH PBr
KCN H /Pt
(2) X ⎯⎯⎯
3
→ ⎯⎯⎯ → ⎯⎯⎯⎯
2
→ Y
(3) CH3CH2COOH (4) (CH3)2CHCOOH
KCN H O+
(3) X ⎯⎯⎯→ ⎯⎯⎯→
3
Y

40
 HCN PBr H O+
(4) X ⎯⎯⎯→ ⎯⎯⎯
3
→ ⎯⎯⎯→
3
Y
51. Consider the following reaction. 54. Consider the following sequence of
reactions
O
|| H+ H O+1. CH3MgI
CH3 -C -O18 -C2H5 +H2O16 ⎯⎯⎯ → CH3CCH ⎯⎯⎯
3
2+ → A ⎯⎯⎯⎯
2. H O
⎯→B
Hg 2

The products formed in the reaction are The final product (B) is :

O (1) CH3CCCH3
||
(2) CH3COCH2CH3
(1) CH3 − C − O16H and C2H5O18 H
(3) CH3CH2CHOHCH3
O
|| (4) (CH3)3 C – OH
(2) CH3 − C − O16H and C2H5O16H

O 55. Reaction of ethyl formate with excess of

||
(3) CH3 − C − O18H and C2H5O16 H CH3MgI followed by hydrolysis gives:

(1) n-Propyl alcohol

O
|| (2) Ethanal
(4) CH3 − C − O18H and C2H5O18 H
(3) Propanal

(4) Isopropyl alcohol

52.
56. When CH3MgI reacts with CH3CN and the

In the above sequence of reactions the end product is hydrolysed, we get-

(1) Propanal
product (C) is :
(2) Acetone
(1) (2)
(3) Formaldehyde
(4) Acetaldehyde
(3) (4)

57. Consider the following reaction sequence.

CH3C  CH ⎯⎯⎯⎯
aq.H2SO4
HgSO
→ A ⎯⎯⎯
PCl5
heat
→B
4

53. The acid formed when propyl magnesium The product (A) and (B) are, respectively :
bromide is treated with CO2 is : (1) CH3COCH3 and CH3CCl2CH3

(1) CH3CH2COOH (2) CH3CH2CHO and CH3CH2CHCl2

(3) CH3CHOHCH3 and CH3CHClCH3

(2) C3H7COOH
(4) CH3CH2CH2OH and CH3CH2CH2Cl
(3) CH3CH2CH2CH2COOH

(4) None of these

41
 59. The final product S in the following
+
H3O
58. + ⎯⎯⎯
THF
→ A ⎯⎯⎯
CO2
→ B ⎯⎯⎯ → reaction sequence is

CH3Cl NBS KCN

Anhy.AlCl3
P Q R S
C. End product C is :
CH3
(1)
COOH

(1) (2) CH3

(2)
COOH

CH2–COOH
(3)

(3) (4) CH3

(4)
COOH

ANSWER KEY
Que. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25
Ans. 3 1 4 2 4 3 1 3 4 4 3 1 3 2 4 3 4 2 1 2 2 4 2 2 2
Que. 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50
Ans. 2 4 2 1 2 3 3 1 3 3 3 1 1 3 4 3 3 4 1 2 3 1 2 3 1
Que. 51 52 53 54 55 56 57 58 59
Ans. 1 3 2 4 4 2 1 2 3

42
 Exercise-II
1. Which of the following pairs of carbonyl H3 C CH3

compounds and Grignard reagent should (4)

O
be chosen as reactants to prepare 2, 4- H3C

dimethyl-3-pentanol ?
(1) CH3CH2CH2CHO and CH3CH2CH2MgBr
(2) (CH3)2CHCHO and (CH3)2 CHMgBr H O+ HBr
4. CH3MgBr + ⎯⎯⎯⎯
3
→ (A) ⎯⎯⎯ → (B)
(3) CH3CH2COCH3 and (CH3)2 CHMgBr O
(4) (CH3)2CHCHO and CH3CH2CH2MgBr Mg/ether
⎯⎯⎯⎯⎯ → (C) ⎯⎯⎯⎯
HCHO
+
→ (D)
H3O

2. Among the given compounds, the most

The end product (D) is :
susceptible to nucleophilic attack at the
carbonyl group is :
(1) (2) CH2 OH
(1) MeCOOCOMe (2) MeCHO
CH 3 CH 2OH CH3
(3) MeCOOMe (4) MeCOCl
OH

3. CH3 − C − CH2 − CH2 − CH2Cl ⎯⎯⎯⎯⎯

CH3MgBr
→ A,
|| (3) CH3 (4)
O CH3 CH2 OH

product A is :
CH3 5. Methyl acetate on treating with excess of
|
CH3 CCH2 CH2 CH2 Cl C2H5MgBr produces :
(1) |
OH CH3 C 2H 5
(2) CH3 ||
CCH2 CH2 CH2 CH3
(1) CH3 –C–OH (2) CH 3–C –OH
O
CH3 C 2H 5
CH3
(3) C 2H 5 CH3
O CH3 C 2H 5–C –OH CH3 –C–OH
(3) (4)
C 2H 5 C 2H5

ANSWER KEY
Que. 1 2 3 4 5
Ans. 2 4 3 1 2

43
 Exercise – III (Previous Year Question)
1. Consider the following compounds : 5. A strong base can abstract an -hydrogen
from [AIPMT-2008]
(i) (ii)
(1) Ketone (2) Alkane
(iii) (iv) (3) Alkene (4) Amine
The correct order of reactivity towards
6. H2COH.CH2OH on heating with periodic
hydrolysis is: [AIPMT-2007]
(1) i > ii > iii > iv (2) iv > ii > i > iii
acid gives :- [AIPMT-2009]

(3) ii > iv > i > iii (4) ii > iv > iii > i
(1) (2) 2CO2

2. Which one of the following on treatment with CHO

(3) 2HCOOH (4)
50% aq. NaOH yields the corresponding CHO

alcohol and acid [AIPMT-2007]

7. Propionic acid with Br2/P yields a dibromo
(1) C6H5CHO
product. Its structure would be :
(2) CH3CH2CH2CHO
[AIPMT-2009]
(3) CH3COCH3
Br
(4) CH3CHO
CH3–C–COOH
(1)
Br
3. The product formed in aldol reaction is : (2) CH2Br–CHBr–COOH
[AIPMT-2007] Br
(1) a -hydroxy aldehyde or ketone H–C–CH2COOH
(3)
(2) an -hydroxy aldehyde or ketone Br
(4) CH2Br–CH2–COBr
(3) an  - unsaturated ester
(4) a -hydroxy acid 8. In a set of reactions, ethyl benzene
yielded a product D
4. Acetophenone when reacted with a base,
C2H5ONa, yields a stable compound which
‘D’ would be: [AIPMT-2009]
has the structure :- [AIPMT-2008]

(1)
(1)
(2)
(2)

(3) (3)

(4)
(4)

44
9. Which of the following reactions will not 14. An organic compound ‘A’ on treatment
result in the formation of carbon-carbon with NH3 gives ‘B’ which on heating gives ‘C’.
bonds? [AIPMT-2010] ‘C’ when treated with Br2 in the presence of
(1) Friedel-Crafts acylation KOH produces ethylamine. Compound ‘A’ is:
(2) Reimer-Tieman reaction
[AIPMT Mains-2011]
(1) CH3CH2COOH (2) CH3COOH
(3) Cannizzaro reaction
(3) CH3CH2CH2COOH (4)
(4) Wurtz reaction

10. The suitable reagent to convert

15. Decarboxylation occurs with maximum
CH3CH=CH–CHO into CH3–CH2CH2–CH2–OH
rate in : [AIIMS-2011]
is : [AIIMS-2010]
(1) NaBH4 (2) LiAlH4 (1) CH3COOH

(3) Zn – Hg/HCl (4) H2/Pd (2) C6H5–COOH

(3) C6H5–CH2COOH
11. : (4) CH3COCH2COOH

[AIIMS-2010] 16. In the following sequence of reactions

(1) KCN H O+ LiAlH
CH3 − Br ⎯⎯⎯→ A ⎯⎯⎯⎯
3
→ B ⎯⎯⎯⎯ 4
ether
→ C,

(2) the end product (C) is :

[AIPMT Pre. 2012]
(3)
(1) Acetaldehyde (2) Ethyl alcohol
(3) Acetone (4) Methane
(4)
17. Predict the products in the given reaction.
12. In a set of reactions m-bromobenzoic [AIPMT Pre. 2012]
acid gave a product D. Identify the CHO
product D [AIPMT Pre.-2011] 50% KOH

Cl
CH2OH COO¯
(1) +

(1) (2) Cl Cl
CH2OH COO¯
(2) +
(3) (4) OH OH
CH2OH CH2COO¯
(3) +
13. Clemmensen reduction of a ketone is
Cl Cl
carried out in the presence of which of
CH2OH OH
the following? [AIPMT Pre.-2011] (4) +
(1) Glycol with KOH
(2) Zn-Hg with HCl OH OH
(3) LiAlH4
(4) H2 and Pt as catalyst

45
18. CH3CHO and C6H5CH2CHO can be
distinguished chemically by : 23. products is
[AIPMT Pre. 2012]
(1) Tollen’s reagent test
(2) Fehling solution test [AIIMS-2015]
(3) Benedict test
(4) Iodoform test
(1) (2)
19. Consider the following reaction :

(3) (4)
The product ‘A’ is : [AIPMT Mains-2012]
(1) C6H5COCH3 (2) C6H5Cl
(3) C6H5CHO (4) C6H5OH

20. Reaction by which Benzaldehyde cannot

be prepared :- [NEET UG-2013] 24. product

(1) + Zn/Hg and conc. HCl Product of above reaction is

[AIIMS-2015]
(2) +CrO2Cl2 in CS2 followed by H3O

(3) + H2 in presence of Pd + BaSO4

(1) (2)
(4) +CO+HCl in presence of anhydrous

AlCl3

21. Which of the following reagents cannot be (3) (4)

used to prepare acetophenone:
[AIIMS-2014]
25. The correct structure of the product A
(1) C6H5COCl + (CH3)2Cd
formed in the reaction
(2) C6H5COCl + CH3MgBr
(3) C6H5CN + C2H5MgBr
(4) C6H6 + (CH3CO)2O/AlCl3 is :-

[NEET-II- 2016]
22. An organic compound ‘X’ having molecular
formula C5H10O yields phenyl hydrazone
and gives negative response to the
(1) (2)
iodoform test and Tollen’s test. It
produces n-pentane or reduction. ‘X’
could be :- [AIPMT-2015]
(1) 2-pentanone (2) 3-pentanone (3) (4)
(3) n-amyl alcohol (4) pentanal

46
26. The correct statement regarding a
carbonyl compound with a hydrogen atom
29.
on its alpha carbon, is :- [NEET-I- 2016]
P will be :-
(1) a carbonyl compound with a hydrogen
(1) Pd/BaSO4 + H2 (2) LiAlH4
atom on its alpha-carbon never
(3) NaBH4 (4) Pd + H2
equilibrates with its corresponding enol.
(2) a carbonyl compound with a hydrogen
atom on its alpha-carbon rapidly 30. Of the following, which is the product
equilibrates with its corresponding formed where cyclohexanone undergoes
enol and this process is known as aldol condensation followed by heating? :
aldehyde-ketone equilibration. [NEET-2017]
(3) a carbonyl compound with a hydrogen
atom on its alpha-carbon rapidly (1) (2)
equilibrates with its corresponding
enol and this process is known as
(3) (4)
carbonylation.
(4) a carbonyl compound with a hydrogen
atom on its alpha-carbon rapidly
equilibrates with its corresponding
31. Consider the reactions : [NEET-2017]
enol and this process is known as
keto-enol tautomerism. silver mirror observed

27. Which of the following reagents would

distinguish cis-cyclopentane-1,2-diol from
its trans-isomer? [NEET-I- 2016]
Identify A, X, Y and Z
(1) Acetone
(1) A-methoxymethane, X-Ethanoic acid,
(2) Ozone
Y-Acetate ion, Z-hydrazine
(3) MnO2
(2) A-methoxymethane, X-Ethanol,
(4) Aluminium isopropxide
Y-Ethanoic acid, Z-Semicarbzide.
(3) A-Ethanal, X-Ethanol, Y-But-2-enal,
Z-Semicarbazone.
28.
(4) A–Ethanol, X–Acetaldehyde,
P & Q respectively are : [AIIMS-2016] Y–Butanone, Z–Hydrazone.

(1) CrO3/H3O, 32. Carboxylic acid have higher boiling points

than aldehydes, ketones and even
(2) CrO2Cl2/H3O, alcohols of comparable molecular mass.
It is due to their [NEET(UG) 2018]
(1) formation of intramolecular H-bonding
(3) NaOCl/,
(2) formation of carboxylate ion
(4) KMnO4/H, (3) more extensive association of carboxylic
acid via van der Waals force of attraction
(4) formation of intermolecular H-bonding

47
33. Compound A, C8H10O, is found to react with
NaOI (Produced by reacting Y with NaOH) and
yields a yellow precipitate with characteristic
smell. A and Y are respectively:
[NEET(UG) 2018]
36. Which of the following acid will form an
(a) Anhydride on heating and (b) Acid
imide on strong heating with ammonia ?
[NEET(UG) (Covid-19) 2020]

(1) COOH
COOH

(2) (1) (2)

COOH COOH

CH3–OH and I2 COOH

(3) OH
OH
CH3
(3) (4)
COOH COOH
(4) CH3 OH and I2
37. Identify compound (A) in the following
reaction: [NEET(UG) (Covid-19) 2020]
34. The reaction that does not give benzoic
acid as the major product is:
A
[NEET(UG) (Odisha) 2019]
CH2OH (1) Benzoyl chloride
K2Cr2O7
(1) (2) Toluene
(3) Acetophenone
COCH3 (4) Benzoic acid
(i) NaOCl
(2) (ii) H2O+
38. The product formed in the following
CH2OH chemical reaction is : [NEET(UG) 2021]
PCC
O O
(3) (Pyridinium
chlorochromate) CH2–C–OCH3

CH2OH ?
CH3
KMnO4/H+
(4) O
OH
CH2–C–OCH3
(1) OH
35. Reaction between benzaldehyde and CH3
acetophenone in presence of dilute NaOH O
CH2–CH2–OH
is known as: [NEET(UG) 2020]
(2)
(1) Cross Aldol condensation CH3
(2) Aldol condensation OH O
CH2–C–CH3
(3) Cannizzaro’s reaction
(3) OH
(4) Cross Cannizzaro’s reaction CH3
OH O
CH2–C–OCH3
(4)
CH3

48
39. Match List - I with List - II. 41. Match List-I with List-II. [NEET(UG) 2022]
[NEET(UG) 2021] List-I List - II
List-I List - II a Cyanohydrin i NH2OH
a i Hell-Volhard b Acetal ii RNH2
CO, HCl
Anhyd, Zelinsky c Schiff’s base iii alcohol
AlCl3/CuCl
reaction d Oxime iv HCN
b O ii Gattermann- Choose the correct answer from the
R–C–CH3 + NaOX ⎯→ Koch reaction options given below:
c R–CH2–OH + RCOOH iii Haloform (1) (a)-(iii), (b)-(iv), (c)-(ii), (d)-(i)
Conc.H SO
⎯⎯⎯⎯⎯⎯
2 4
→ reaction (2) (a)-(ii), (b)-(iii), (c)-(iv), (d)-(i)
(3) (a)-(i), (b)-(iii), (c)-(ii), (d)-(iv)
d R–CH2–COOH iv Esterification
(i) X /Red P
(4) (a)-(iv), (b)-(iii), (c)-(ii), (d)-(i)
⎯⎯⎯⎯⎯⎯
2
(ii) H O
→
2
dry H3O+
42. RMgX + CO2 Y ⎯⎯⎯⎯ → RCOOH
ether
Choose the correct answer from the What is Y in the above reaction?
options given below. [NEET(UG) 2022]
(1) (a)-(iv), (b)-(i), (c)-(ii), (d)-(iii) (1) RCOO–Mg+X
(2) (a)-(iii), (b)-(ii), (c)-(i), (d)-(iv) (2) R3CO–Mg+X
(3) (a)-(i), (b)-(iv), (c)-(iii), (d)-(ii) (3) RCOO–X+
(4) (a)-(ii), (b)-(iii), (c)-(iv), (d)-(i) (4) (RCOO)2Mg

40. The intermediate compound ‘X’ in the 43. Which one of the following is not formed
following chemical reaction is: when acetone reacts with 2-pentanone in
[NEET(UG) 2021] the presence of dilute NaOH followed by
heating? [NEET(UG) 2022]
O CH3

H3C CH3
(1)
CH3

CH3 CH3
(1) O CH3
(2)
CH3 O

(2) CH3 CH3

(3)
CH3
CH3 CH3
(3)
CH3 O
(4)

(4)

49
44. Compound X on reaction with O3 followed 46 . Weight (g) of two moles of the organic
by Zn/H2O gives formaldehyde and 2- compound , which is obtained by heating
sodium ethanoate with sodium hydroxide
methyl propanal as products. The
in the presence of calcium oxide is:
compound X is: [NEET(UG) 2022]
[NEET(UG) 2023]
(1) 3-Methylbut-1-ene
(1) 18
(2) 2-Methylbut-1-ene
(2) 16
(3) 2-Methylbut-2-ene
(3) 32
(4) Pent-2-ene
(4) 30

47. Identify the major product obtained in the

45. The products A and B in the following
following reaction:
reaction sequence are :
[Re-NEET (UG) 2022] [NEET(UG) 2023]

(i) HBr (i) SOCl2

Ph A B
(ii) Mg, dry ether (ii) CH3–NH2
(iii) CO2, H3O+
O

(1) A= OH ;

O
CH3
B= N
H
48. Given is a reaction of your reference:
OH
[NEET(UG) 2023]
(2) A= O ;

H
N
B= CH3
O
OH
(3) A= ;

H
N
B= CH3

(4) 49. Consider the given reaction:

A= OH
;
The functional groups present in the
compound " X" are:
CH3
N [NEET(UG) 2023]
B= H
(1) Ketone and double bond
(2) Double bond and aldehyde
(3) Alcohol and aldehyde
(4) Alcohol and ketone

50
50. Identify the product (A) in the following 52 . Identify the product in the following
reaction: reaction:
[NEET(UG) 2023] [NEET(UG) 2023]

53. Identify the final product [D] obtained in

the following sequence reaction:
[NEET(UG) 2023]

51. The following conversion is known as:

[NEET(UG) 2023]

(1) Stephen reaction

ANSWER KEY
(2) Gattermann-Koch reaction
Que. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25
Ans. 3
(3)
1
Etard
1
reaction
3 1 1 1 1 3 4 1 3 2 1 4 2 1 4 3 1 3 2 4 1 4
Que. 26 (4)
27 Rosenmund
28 29 30 reaction
31 32 33 34 35 36 37 38 39 40 41 42 43 44 45
Ans. 4 1 2 1 2 3 4 3 3 1 1 1 4 4 1 4 1 2 1 2

51