Aldehydes Ketones and Carboxylic Acids

NEET
REVISION SERIES
ALDEHYDE, KETONE AND CARBOXYLIC ACID
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Q-1 - 12774774
An optically active compound molecular formalC5 H12 O(X). X
oxidation with CrO3 / H2 SO4 given an actiral C5 H10 O. Hence , X
could be
(A)
(B)
(C)
(D)
CORRECT ANSWER: A
SOLUTION:
oxidation of X giving ketone as well as X is chiral, it must
be a seconadary alcohol with α chiral carbon.
Watch Video Solution On Doubtnut App
Q-2 - 12774775
When CH2 = CHOOH is reduced with LiAIH4 ., the compound
obtained is
(A) CH3 CH2 CH2 OH
(B) CH3 CH2 CHO
(C) CH 3 CH2 COOH

(D) CH 2 = CHCH2 OH
CORRECT ANSWER: D
SOLUTION:
CH 2 = CHCOOH
LiAIH4
−−−−→ CH2
= CHCH2 OH
Double bond is not affected.
Q-3 - 12774776
Which regent below cannot reduced with an acid chloride to an
aldehyde?
(A) P d / BaSO4
(B) Na / C2 H5 OH
(C)
LiAlH[OC(CH3 )3 ]3 at
∘
− 80 C
(D)
[AlH{CH2 CH(CH3 )2
}2 ]at − 80 C ∘
CORRECT ANSWER: B
SOLUTION:
Na / C2 H5 OH further reduces to alcohols.
Q-4 - 12774780
Compound which gives acetone on ozonolysis
(A)
CH 3 − CH = CH
− CH3
(B) (CH3 )2 C = C(CH3 )2
(C) C6 H5 CH = CH2
(D) CH 3 CH = C = CH2
CORRECT ANSWER: B
SOLUTION:
O3
(CH3 )2 −−→ 2CH3
− CO − CH3
Q-5 - 12774781
A hydrocarbon X has molecular formula C5 H10 . X on tratement
with B2 H6 in H2 O2 / NaOH given an optically active C5 H12 O
which on tratment with CrO3 /HCL/ pyridine gives C5 H10 O

which is still chiral. Which of the following can be a produce of
reductive ozonolysis of X?
(A)
O
∣∣
CH 3 − CH2 − C
− CH3
O
∣∣
(B) CH3 − C − CH3
CH3
∣
(C) CH 3 − CH − CHO
(D)
CORRECT ANSWER: C
SOLUTION:
Q-6 - 12774782
The most suitable regent for the conversion of

R − CH2 − OH → R
− CHO
is
(A) KMnO4
(B) K2 Cr2 O7
(C) CrO3
(D) P CC [Pyridinium chlorochromate]

CORRECT ANSWER: B
SOLUTION:
Mild oxidizing agents like P CC [Pyridinium
chlorochromate] are particularly used for the conversion
of
R − CH2 OH → R
− CHO
.
Q-7 - 12774783
Predict the product 'B' in the sequence of reaction

30 % H 2SO4 N aOH
HC = CH −−−−−−→ A −−−→ B
HgSo4
(A) CH3 COONa
(B) CH3 COOH

(C) CH 3 CHO
(D)
CH 3 − CH = CH
− CHO
CORRECT ANSWER: D
Q-8 - 12774784
CH3 COCI
2H
−−−−−−→ CH3 CHO + HCI
Pd / BaSO4
The above reaction is called
(A) Reimer - Tiemann reaction
(B) Cannizaro reaction
(C) Rosenmund reaction

(D) Reformatsky reaction
CORRECT ANSWER: C
SOLUTION:
CH 3 COCI
2H
−−−−−−→ CH3 CHO
P d / BaSO4
+ HCI
Q-9 - 12774785
What is the final major product of the following reaction
CH3 − CH2 − C = C − H
NaN H2 CH3 CH2 CH2 − Br HgSO4
−−−−→ −−−−−−−−−−→ −−−→ ?
H 2SO4
(A)
(B)
(C)
(D)
CORRECT ANSWER: B
SOLUTION:
Q-10 - 12774787
Consider the following reaction sequence
KMnO4 ( dili . ) N aI O
−−−−−−−−−→ −−→ Final major product X
HO H 3O
The correct statement regarding X is
(A) It has an aldehyde functional group
(B) It has both aldehyde and ketone functional group
(C) It has a ketone functional group
(D) It has a ketone and an acid functional group
CORRECT ANSWER: B
SOLUTION:
Q-11 - 12774792
Banzaldehyde can be prepared by oxidation of toluene by
(A) Acidic KMnO4
(B) K2 Cr2 O7
(C) CrO2 CI2
(D) All of these
CORRECT ANSWER: C
SOLUTION:

This is Etard's reaction
Q-12 - 12774794
Which of the following compound gives a ketone with Grignard
reagent?
(A) Formaldehyde
(B) Ethyl alcohol
(C) Methyl cyanide
(D) Methyl iodide
CORRECT ANSWER: C
SOLUTION:
Q-13 - 12774802
The regent used in Gattermann -Koch aldehyde symthesis is
(A) P d / BaSO4
(B) alkaline KMnO4
(C) acidic KMnO4
(D) CO + HCI
CORRECT ANSWER: D

Q-14 - 12774804
On reductive
ozonolysis yields
(A) 2- oxoheptanal
(B) 6- oxoheptanoic acid
(C) 6- hydroxyheptanal
(D) 3- hydroxyheptanal
CORRECT ANSWER: A
SOLUTION:
Q-15 - 12774805
An alkene of molecular formula C9 H18 on ozonolysis gives 2.2
dimethyl propanal and 2- butanone, then the alkene is
(A) 2, 2, 4 - trimethyl - 3 - hexene
(B) 2, 2, 6 - trimethyl - 3 - hexene
(C) 2, 3, 4 - trimethyl - 2 - hexene
(D) 2, 2, 4 - trimethyl - 2 - hexene
CORRECT ANSWER: A
SOLUTION:
Q-16 - 12774812
The correct order of reactivity of Ph Mg Br with

O
∣∣
Ph − C − Ph
C
(I)
O
∣∣
CH3 − C − H
( II )
O
∣∣
CH3 − C − CH3
( III )
is
(A) (I) gt (II) gt (III)
(B) (III) gt (II) gt (I)
(C) (II) gt (III) gt (I)
(D) (I) gt (III) gt (II)
CORRECT ANSWER: C
SOLUTION:
Reaction of P hMgBr with carbonyl compoundis an
example of nucleophilie addition oncarbon-deficiency of

carbonyl carbon and less steric hindrence on carbonyl
carbon.
The acetaldehyde I is the most reactiove
C6 H3 COC6 H5 least
Q-17 - 12774814
The major product in the fgollowing reaction is

(A)
(B)
(C)
(D)
CORRECT ANSWER: D
SOLUTION:

Q-18 - 12774813
The major product H of the given reaction sequence is

CH3 − CH2 CO − CH3
ΘCN 95 % H2 SO4
−−→ G − −−−−−−→ H
Heat
(A)
CH 3 − CH = C
∣
CH3
− COOH
(B)
CH 3 − CH = C
∣
CH3
− CN
(C)
OH
∣
CH 3 − CH2 − C
∣
CH3
− COOH
(D)
CH 3 − CH = C
∣
CH3
− CO − NH2
CORRECT ANSWER: A
SOLUTION:
This is example of nucleophile addition on cathonyl
compounds
Q-19 - 12774816
P- cresol react with chloroform in alkaline medium to give

compound (A) which adds HCN to form (B). The latter on acidic
hydrolysis given chiral carboxylie acid. The structure of carboxylic
acid is :
(A)
(B)
(C)
(D)
CORRECT ANSWER: B
SOLUTION:
Q-20 - 12774833
In the following reactiona, the product S is
(A)
(B)
(C)
(D)
CORRECT ANSWER: A
SOLUTION:

Q-21 - 12774838
What would be the major product in the following reaction?
(A)
(B)
(C)
(D)
CORRECT ANSWER: A
SOLUTION:
LiAIH4 reduces both carbonyls and carboxylie group
but does not reduce olefinit bond
Q-22 - 12774840
Which one of the following pairs is not correctly matched ?

(A)
>C =O
Clemenson's reduction
−−−−−−−−−−−−→
> CH2
(B)
>C =O
Wolff -Kishner reduction
−−−−−−−−−−−−−−→
> CHOH
(C)
− COCI
Resenmund's reduction
−−−−−−−−−−−−−→
− CHO
(D)
Stephen reduction
− C ≡ N −−−−−−−−−−→
− CHO
CORRECT ANSWER: B
SOLUTION:
Wolff-Kishner reduction does not convert gt CO to

CHOH but conversis it to > CH2 .
Q-23 - 12774846
Which compound given below does not form red precipitate with
ammobniacal solution of Cu(II) tartarate?
(A) H2 CO
(B) CH3 − C ≡ CH
(C) CH 3 CHO
(D) C6 H5 CHO
CORRECT ANSWER: D
SOLUTION:
Fehling's test is not given by banzaldehyde (aromatic

aldehyde).
Q-24 - 12774847
Which reagent can differentiate between benzaldehyde and
distinguished by
2+
(A) [Cu(NH3 )4 ]
+
(B) [Ag(NH 3 )2 ]
(C) NaOH / I2
(D) Both (b) and ( c)
CORRECT ANSWER: D
SOLUTION:
Benzaldehyde gives Tollens test acetophenone does

not. On the other hand, acetophenone
(P h − COCH3 ) gives iodoform test but benzaldehyde
does not.
Q-25 - 12774861
When acetaldehyde is heated with Fehling's solution it gives a
precipitate of
(A) Cu
(B) CuO
(C) Cu2 O
(D) Cu + Cu2 O + CuO
CORRECT ANSWER: C
SOLUTION:
CH 3 CHO
2+ −
+ 2Cu + OH
(Fehling solution)
→ CH3 COOH
+ ) (Cu2 O ) −
(red
Q-26 - 12774862
In the following reaction sequence, the correct structures of (E ), (F)
and (G) are:
(*implies 13C-labelled carbon)
(A)
(B)
(C)
(D)
CORRECT ANSWER: C
SOLUTION:
β-keto acids undergo decarhonylation by simple heating
from that we get carbonyl compound of type

O
∣∣
CH 3 − C -which undergoes iodoform reaction.

Q-27 - 12774881
Consider the following reaction
A `"dicarbony"l overset (NaOH ("Dil"))underset ("Aldol") to
overset ((Ph_(3)P)_(3) RhCI) to
Which of the Iabeled C - C hond formation is not possible in the
above reaction?
(A) Only iv
(B) Only iii
(C) Only ii
(D) Only i
CORRECT ANSWER: D
SOLUTION:
An α − βC − C bond is always formed in aldol
reaction.
Q-28 - 12774882
In the following reaction

CH2 O + CH3 − N O2
DilN aOH ConeH2 SO4
−−−−−→ −−−−−−→
Heat
The major oranic product is

O
∣∣
(A) H − C − CH2 − NO2
(B) CH2 = CH − NO2
(C)
HO − CH2 − CH2
− NO2
(D)
CORRECT ANSWER: B
SOLUTION:
HO −
¯¯¯H 2
CH 3 NO2 −−→ C
− NO2
O
CH2 O ∣ ∣
CH 2 − NO2 −−
−→ C H2
Δ
− CH2 − NO2 −−→
product
Q-29 - 12774894
The major organic product in the following reaction is
O
∣∣
(A) C6 H 5 − C − COOH
OH
∣
(B) C6 H 5 − CH − COOH
OH
∣
(C) C6 H5 − CH − CHO
(D)
OH
∣
C6 H5 − CH
− CH2 OH
CORRECT ANSWER: B
SOLUTION:
Q-30 - 12774902
In a Cannizaro reaction the intermediate that will be the best
hydride donor is
(A)
(B)
(C)
(D)
CORRECT ANSWER: D
SOLUTION:
− NO2 is an electron withrowing nitro group.
Presence of electron withdrawing nitro group facilitates
the rease of hydride ion.
Q-31 - 12774903
Which m-pchlorobenzaldehyde is treated with 50 % KOH

solution, the product (s) obtained is (are)
(A)
(B)
(C)
(D)
CORRECT ANSWER: C
SOLUTION:
It is Cannizzaro reaction
Q-32 - 12774905
(A)
(B)
(C)
(D)
CORRECT ANSWER: C
SOLUTION:
Q-33 - 12774922
What is the correct about the following reaction

CH3 − C H2 − CH − CH3
∣
Br
Mg ( i ) CO2
−−−−−→ −−−−−→
+
( C2 H 5 ) 2 O ( ii ) H3O
(A) The major product is recemic mixture of 2- methyl
butanoic acid
(B) The major product is achiral 2-methyl butanoic acid
(C) If a pure enantiomer of starting compound is taken,
the major product would be a pure enaniomer of 2-
methyl butanoic acid
(D) The major product would be trans-2-butene
CORRECT ANSWER: A
SOLUTION:

Recemic Griganard reagent is formed which gives
recemic product.
Q-34 - 12774924
CL2
CH3 CH2 COOH −−→ (A)
RedP
Alc . KOH
−−−−−→ (B)
What is (B)?
(A) CH3 CH2 COCl
(B) CH3 CH2 CHO
(C) CH 2 = CHCOOH
(D) ClCHCH2 COOH
CORRECT ANSWER: C
SOLUTION:
CH 3 CH2 COOH
cl2
−−→ CH3 CHCICOOH
Red
Alc . KOH
−−−−−→ CH2
− HCI
= CHCOOH
Q-35 - 12774934
Which reaction sequence gives below 5-methyl hexanoic acid?
(A)
(B)
(C)
(D)
CORRECT ANSWER: D
SOLUTION:
Q-36 - 12774943
The acid which reduces Fehling sodium is
(A) Methanoic acid
(B) Ethanoic acid
(C) Butanoic acid
(D) Propanoic acid
CORRECT ANSWER: D
SOLUTION:
Methanoic acid resembles with aldehyde due to its
O
∣∣
structure So, it reduces Fetling reagent. H − C − OH
Aldehydic group
Q-37 - 12775016
Choose the best method that could performed the following
transformation.
(A)
EtOH EtON a C6 H5 CH2 Br
−−−−−→ −−−→ −−−−−−→
H + / Heat
( i ) HO −
−−−−−−−−→
( ii ) H ⊕ / Heat
(B)
LDA C6 H5 CH2 Br
−−→ −−−−−−→
( i ) HO −
−−−−−−−−→
( ii ) H + / Heat
HO − EtOH C6 H5 CH2 Br
(C) −−→ −−
−→ −−−−−−→
+ H
(D)
OH − C6 H5 CH2 Br
−−→ −−−−−−→
( i ) HO −
−−−−−−−−→
( ii ) H + / Heat
CORRECT ANSWER: A
SOLUTION:
Q-38 - 12775017
Arrange the following esters in the following order of reactivity in
base catalysed hydrolysis reaction.

(A) III < I < II < IV
(B) Iv < III < II < I
(C) I < II < III < IV
(D) IV < II < I < III
CORRECT ANSWER: A
SOLUTION:
Electron withrawing group increases electrophilic
character of ester, hence reactivity in hydrolysis reaction.
(IV) ismost reactive as it has the best leaving group.

Q-39 - 12775087
The major organic formed in the following reaction is
(A)
(B)
(C)
(D)
CORRECT ANSWER: D
SOLUTION:
Q-40 - 12775088
In a act of reactions, acid yielded a product D

SOCI2
CH3 COOH −−−→ A
Benzene HCN HOH
−−−−−−→ B −−→ C −−→ D
Anhy . AlCl3
.
(A)
(B)
(C)
(D)
CORRECT ANSWER: A
SOLUTION:
CH 3 COOH
O
SOCl2 ∣∣
−−−−−−−−→ CH3 − C
Thionylchloride
− Cl
Benzene
−−−−−−−−−−−→
AnhyAlCl3
Friedel−Craft
acylation
Q-41 - 12775098
Acetophenone when reacted with a base C2 H5 Ona yields a stable
compound which hasthe structure
(A)
(B)
(C)
(D)
CORRECT ANSWER: D
SOLUTION:
It is condensation reaction.

Q-42 - 12775100
Trichlorroacetaldehyde, CCI3 CHO. Reacts with chlorobenzene in
presence of sulphuric acid and produces.
(A)
(B)
(C)
(D)
CORRECT ANSWER: A
SOLUTION:
It is preparation of DDT.
Q-43 - 12775136
o − T oluic acid on reaction with Br2 + F e gives
(A)
(B)
(C)
(D)
CORRECT ANSWER: C
SOLUTION:
In o-toluic acid, − CH3 group is ortho-para directing
and − COOH group is meta-directing. So the resulting
product will be ( c) in which Br is attached at para to
− CH3 and meta to − COOH group.
Q-44 - 11485845
Compounds (B) and (C ), respectively, are:
(A)
(B)
(C)
(D)
CORRECT ANSWER: C
SOLUTION:
Q-45 - 11485847
NaNH 2 H3O ⊕
M e − ≡ − H −−−−−−→ (C ) −−−→ (D)
+ liq . N H3
the final product (D) is:
(A)
(B)
(C)
(D) All
CORRECT ANSWER: A
SOLUTION:
Q-46 - 11485848
Compound
(B) is:
(A)
(B)
(C)
(D) All
CORRECT ANSWER: A
SOLUTION:
This is an example of Benzil-Benzilic acid rearrangement

?
reaction. OH attacks at the more reactive (C = O)
group, (containing more EWG or less EDG). Et is more
EDG than Me (due to +I effect, here no H.C.). Therefore,

?
OH attacks (C = O) with (Me)group.
Q-47 - 11485854
Two moles of HCHO and 1 mol of PhCHO react with conc. NaOH.
What are the products quantitatively?
(A) 1 mol of HCOONa, 1 mol of P hCH2 OH , and 1 mol
of PhCOONa.
(B) 1 mol of HCOONa, 1 mol of P hCH2 OH , and 0.5
mol of PhCOONa.
(C) 1 mol of HCOONa, 1.5 mol of P hCH2 OH , and 0.5
mol of PhCOONa.
(D) 1 mol of HCOONa, 2 mol of P hCH2 OH , and 2 mol
of PhCOONa.
CORRECT ANSWER: C
Q-48 - 11485869
The final product (E ) in the following reaction is:

(A)
(B)
(C)
(D)
CORRECT ANSWER: D
SOLUTION:
Q-49 - 11486119
The compound (D) is :
(A) RCOOH
(B) RCH2 OH
(C) R − C ≡ N
(D) RCHO
CORRECT ANSWER: D
SOLUTION:
RCONH2 (B), R − C
≡ N (C), RCHO(D)
.
Q-50 - 11486122
Product (B) in the reaction is :
(A)
(B)
(C)
(D)
CORRECT ANSWER: C
SOLUTION:
Claisen ester condensation.
Q-51 - 11486124
Product (C) is :
(A)
(B)
(C)
(D)
CORRECT ANSWER: B
SOLUTION:
LDA abstract α − H atom to form a carbanion which

reacts with EtI to give product (b).
Q-52 - 11486131
The major product (C) in the reaction is :
(A)
(B)
(C)
(D) All
CORRECT ANSWER: A
SOLUTION:
− OH
Herem 2 group would be sterically more hindered
when ester with bulky (P hCO) group is formed. Hence

− OH
, 1 group reacts.
Q-53 - 11486138
P hCON H2 −−−→ (B) −−−→ (C)

(A) KOBr MeOH
Product is (C) is :
(A) P hNH2
(B) P hNHCOOMe
(C) P hNHCOOP h
(D) None
CORRECT ANSWER: B
SOLUTION:
Hofmann bromamide reactions. The product
(P h − N − C = O) reacts with MeOH to give
urethane
(P h − NH
− COOMe)
.
Q-54 - 11486144
Product (B) is :
(A)
(B)
(C)
(D)
CORRECT ANSWER: D
SOLUTION:
Favorskii reaction.
.
Q-55 - 11485878
Which of the following ketone will not give yellow precipitate with
NaOH / I2 ?
(A) 2-Pentanone
(B) Benzophenone
(C) Acetone
(D) 2-Hexanone
CORRECT ANSWER: B
SOLUTION:
a.
O
∣∣
b. P h − C − P h (No methyl ketone) (negative
iodoform test)
O
∣∣
Me − C − Me (Methyl ketone) (Positive iodoform
test)
d. (Methyl
ketone) (Positive iodoform test)
Q-56 - 11485898
C6 H5 − CH = CHCHO
(X)
−−→ C6 H5 = CHCH2 OH
In the above sequence (X) can be:
(A) H2 / Ni
(B) NaBH4
(C) K2 Cr2 O7 / H +
(D) Both (a) and(b)
CORRECT ANSWER: B
SOLUTION:
P h − CH = CH
− CHO
NaBH4
−−−→ P h − CH = CH
− CH2 OH
NaBH4 does reduce (C = C) and (C ≡ C) bonds.
Q-57 - 11485901
Which of the following will not reduce Fehiling's solution ?
(A) Formic acid
(B) Ethanal
(C) 2-Methyl Propanal
(D) All will reduce
CORRECT ANSWER: D
Q-58 - 11485883
The following reaction is an example of:

RCHOHR' + CH3 COCH3
A1-tert butoxide
−−−−−−−−−−−−→ RCOR'
( ( CH 3 ) 3 C − O ) 3 A1
+ CH3 CHOHCH3
(A) Oppenauer oxidation
(B) Etard oxidation
(C) Pinacol reduction
(D) Beta oxidation
CORRECT ANSWER: A
Q-59 - 11485876
Mild
(CH3 )2 CHOH −−−−−−→ (X)
oxidation[O]
( i ) CH 3Mgl
−−−−−−−−→ (Y )
( ii ) Hydrolysis
In the above sequence of reaction, (Y) is:

(A) Isobutyl alcohol
(B) n-Butyl alcohol
(C) Tertiary butyl alcohol
(D) Isobutylene
CORRECT ANSWER: C
SOLUTION:
Q-60 - 11485862
(C ) can also be obtained from (A) by:
(A) Claisen-Schmidt reaction with HCHO

(B) Cross Cannizzaro reaction with HCHO
(C) Aldol reaction with CH3 CHO
(D) None
CORRECT ANSWER: B
SOLUTION:

Aldehydes Ketones and Carboxylic Acids

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NEET

ALDEHYDE, KETONE AND CARBOXYLIC ACID

Revise Most Important Questions to Crack NEET 2020

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An optically active compound molecular formalC5 H12 O(X). X

oxidation with CrO3 / H2 SO4 given an actiral C5 H10 O. Hence , X

oxidation of X giving ketone as well as X is chiral, it must

be a seconadary alcohol with α chiral carbon.

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When CH2 = CHOOH is reduced with LiAIH4 ., the compound

(A) CH3 CH2 CH2 OH

(B) CH3 CH2 CHO

(C) CH 3 CH2 COOH

Double bond is not affected.

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Which regent below cannot reduced with an acid chloride to an

Na / C2 H5 OH further reduces to alcohols.

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Compound which gives acetone on ozonolysis

A hydrocarbon X has molecular formula C5 H10 . X on tratement

with B2 H6 in H2 O2 / NaOH given an optically active C5 H12 O

which on tratment with CrO3 /HCL/ pyridine gives C5 H10 O

The most suitable regent for the conversion of

(D) P CC [Pyridinium chlorochromate]

Mild oxidizing agents like P CC [Pyridinium

chlorochromate] are particularly used for the conversion

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Predict the product 'B' in the sequence of reaction

(A) CH3 COONa

(B) CH3 COOH

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The above reaction is called

(A) Reimer - Tiemann reaction

(B) Cannizaro reaction

(C) Rosenmund reaction

What is the final major product of the following reaction

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The correct statement regarding X is

(A) It has an aldehyde functional group

(B) It has both aldehyde and ketone functional group

(C) It has a ketone functional group

(D) It has a ketone and an acid functional group

Banzaldehyde can be prepared by oxidation of toluene by

(A) Acidic KMnO4

(C) CrO2 CI2

(D) All of these

This is Etard's reaction

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Which of the following compound gives a ketone with Grignard

(B) Ethyl alcohol

(C) Methyl cyanide

(D) Methyl iodide

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The regent used in Gattermann -Koch aldehyde symthesis is

(B) alkaline KMnO4

(C) acidic KMnO4

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(B) 6- oxoheptanoic acid