BENZALDEHYDE

Total No.of questions in Benzaldehyde are -

Level # 1 .................................................................................... 25
Level # 2 ........................................ ......................................... 25
Level # 3 ........................................ ......................................... 09
Level # 4 ........................................ ......................................... 05

Total No. of questions .............................................................. 64

 LEVEL # 1
Questions general method of preparation Questions Chemical reaction
based on based on

Q.1 By treating toluene with chromyl chloride in Q.8 In connection with benzaldehyde which of the
CCl4 and decomposing the complex with water, following statement is incorrect –
the reaction is named as – (A) –CHO group of benzaldehyde is meta
(A) Etard reaction directing
(B) Sandmeyer’s reaction (B) Benzaldehyde undergoes Claisen
(C) Schotten Baumann reaction condensation
(D) Stephen’s reaction (C) Benzaldehyde on oxidation gives phenyl
acetic acid
Q.2 In the preparation of benzaldehyde by (D) Benzaldehyde on reduction gives benzyl
Stephen’s reaction the main reactant cannot alcohol
be named as –
(A) Phenyl cyanide (B) Benzonitrile
PdBaSO
4
(C) Benzene carbonitrile (D) Benzal cyanide Q.9 C 6 H 5 COCl  
 Intermediate
H2

Q.3 Oxidation of toluene to benzaldehyde has to Oxidation Ca Salt

   Intermediate   A
be easily done with – Dry distillation
(A) Acidic K2Cr2O 7 (B) CrO2Cl 2
Compound (A) in above reaction sequence is –
(C) Acidic KMnO4 (D) Alkaline KMnO4
(A) Benzophenone (B) Benzaldehyde
(C) Acetophenone (D) Benzoquinone
Q.4 Benzaldehyde will be formed in the reaction –
(A) Hydrolysis of C6H5CHCl 2
(B) Ozonolysis of C6H5CH = CH2 NH OH
Q.10 C6H5CHO   2  A H 2O  B

(C) Both the above
(D) None of the above What is not true for the compound B –
(A) Gives cannizaro’s reaction
(i) SnCl /HCl
(B) Acts as strong reducing agent
Pd/BaSO 4 2 
Q.5 A    –CHO  B (C) Gives phenol on reduction
H2 (ii) H2O
(D) Gives optical active compound with HCN
A and B respectively are –
(A) Benzoyl chloride, benzonitrile
(B) Benzyl chloride, benzylnitrile Q.11 An organic aromatic compound containing C,
(C) Benzal chloride, benzonitrile H & O has a characteristic smell of bitter
(D) Benzotrichloride, benzonitrile almonds. This on oxidation with potassium
permanganate gives a monobasic acid. The
sodium salt of which on distillation with
Questions
based on
structure sodalime gives benzene. What is the original
compound –
Q.6 Benzo radical in the following is – (A) C6H5CH2CHO (B) C6H5CHO
(A) C6H5CH2– (B) C6H4< (C) C6H5OH (D) None of the above
(C) C6H5– (D) C6H5 – C
Q.12 Benzaldehyde is oxidised and reduced
Q.7 –CHO group in benzene nucleus – simultaneously in the presence of –
(A) Activates the ring (A) NaHCO3 (B) NaOH
(B) Deactivates the ring (C) Na2CO3 (D) HCl
(C) Does not affect the ring
(D) None of these
 O NH
Q.13 I 
2  Benzaldehyde  
3  II , CN
Q.20 ? EtOH
 Benzoin.
I, II are – ,H O2
(A) Benzoic acid, Benzaldehyde ammonia The reactant is obtained by dry distillation of
(B) Benzoic acid, Hydrobenzamide the calcium salts of the following pairs –
(C) Phenyl acetic acid, Benzaldehyde ammonia (A) C6H5CH2COOH, HCOOH
(D) Benzoic acid, Aniline (B) C6H5COOH, HCOOH
(C) C6H4 (OH)COOH, HCOOH
Q.14 C6H5CHO + PCl5, the product is – (D) C6H4 (NH2)COOH, HCOOH
(A) Benzyl chloride Q.21 Hydrobenzamide is formed in the reaction –
(B) Benzotrichloride (A) C6H5COOH +NH3
(C) Benzal chloride (B) C6H5CHO + NH3
(D)Triphenyl phosphate (C) HCHO + NH3
(D) CH3COCH3 + NH3
Q.15 Benzaldehyde is heated with a conc. solution
of KOH to form – Cl
Q.22 C6H5CHO  
2  A + HCl
(A) C6H5CH2OH
(B) C6H5COOH The product A when reacts with the following
compounds the reaction is known as
(C) C6H5COOK
Schotten Baumann reaction –
(D)C6H5COOK + C6H5CH2OH
(A) C6H5NH2 (B) C6H5CH2OH
Q.16 Benzaldehyde and formaldehyde give a (C) C6H5OH (D) All of these
common reaction –
Q.23 Benzaldehyde shows different reaction than
(A) Cannizzaro’s reaction aliphatic aldehyde with the following reagent –
(B) Benzoin condensation
(A) Tollen’s reagent (B) Schiff’s reagent
(C) Claisen condensation (C) Fehling’s reagent (D) Hydroxylamine
(D) Perkin’s reaction
Q.24 HCHO and C6H5CHO can be distinguished
Q.17 Benzaldehyde can be converted to benzyl by –
alcohol by –
(A) Fehling solution (B) Tollen’s reagent
(A) HCl (C) KMnO4 (D) All of these
(B) NaOH
(C) LiAlH4 Q.25 Which statement is true about benzaldehyde –
(D) B and C are correct (A) It does not react with Tollen’s reagent
(B) It does not react with Fehling’s solution
Q18 Benzyl alcohol from benzaldehyde is obtained (C) It does not react with HCN
in the following reaction – (D) It does not react with NaHSO3
(A) Cannizzaro’s reaction (B) Kolbe’s reaction
(C) Wurtz reaction (D) Fitting’s reaction

Q.19 Benzaldehyde condenses with acetic

anhydride to give cinnamic acid in presence
of –
(A) Sodium acetate (B) Sodium chloride
(C) Sodium benzoate (D) Sodium metal
 LEVEL # 2
Q.1 Benzaldehyde reacts with ammonia to form – Q.9 Replacement of carbonylic oxygen is
(A) Aniline (B) Benzamide observed in the reaction –
(C) Hydrobenzamide (D) Phenyl cyanide (A) C6H5CHO/2H
(B) C6H5CHO/H2N – NH2
Q.2 Which one of the following reactant can be (C) C6H5COOH/PCl5
used to distinguish between benzaldehyde (D) C6H5CHO/HCN
and benzyl alcohol –
Q.10 Use is made of the following reagent to
(A) KMnO4 / oxidation (B) CrO3 / oxidation convert benzaldehyde to benzoyl chloride –
(C) Sodium metal (D) Flame test
(A) Phosphorus pentachloride
(B) Thionyl chloride
Q.3 What are the products formed when a mixture (C) Reaction with chlorine in presence of AlCl3
of benzaldehyde and formaldehyde is heated (D) Reaction with Cl 2
with conc. alkali –
Q.11 Benzyl phenyl ketone is –
(A) Benzyl alcohol and formic acid
(A) C6H5COC6H5
(B) Only benzyl alcohol
(B) C6H5 – CO – CO – C6H5
(C) Methyl alcohol and benzoic acid
(C) C6H5CH2 – CO – C6H5
(D) Only methyl alcohol
(D) C6H5CH2 – CO – CH2 – C6H5

Q.4 Which of the following compounds will react Q.12 The following compound is obtained on refluxing
with ethanolic KCN – benzaldehyde with aqueos ethanolic potassium
cyanide –
(A) C6H5OH (B) CH3COCl
(C) C6H5CHO (D) C6H5COOH (A) Benzoic acid (B) Benzyl acetate
(C) Cinnamic acid (D) Benzoin

Q.5 Benzaldehyde is used in all except – Q.13 An organic compound contains 40% C and
(A) In the manufacture of perfuming agents 6.66% H. Its empirical formula is –
(B) As an oxidising agent (A) CH2 (B) CH2O
(C) CHO (D) CHO2
(C) In the manufacture of dyes
(D) In the manufacture of cosmetics Q.14 Choose the wrong statement –
Q.6 Benzylidene acetone is the product of the (A) Smell of benzaldehyde and mirbane oil is
not different
reaction of an organic compound (A) with
acetone in the presence of ethanolic sodium (B) Benzaldehyde undergoes Tischenko
hydroxide. The organic compounds (A) is – reaction
(A) Benzylalcohol (B) Benzaldehyde (C) Benzaldehyde reduces Fehling’s solution
(C) Benzoic acid (D) Acetophenone (D) Dry distillation of calcium benzoate gives
a ketonic compound
Q.7 Which of the following is most stable –
Q.15 Etard reaction in the following is –
(A) C6H5COO– (B) CH3COO–
(C) C6H5COOH (D) CH3COOH (A) Oxidation of toluene to benzaldehyde by
chromylchloride
NH OH
2  An oxime H2O (B) Oxidation of toluene to benzaldehyde by
Q.8 C6H5CHO    A. alkaline KMnO4
The V. D. of A should be – (C) Dry distillation of calcium benzoate
(A) 53 (B) 52 (D) Reaction of benzene with Cl 2 in the
(C) 51 (D) 50 presence of ultra violet light.
 CH Cl
3 CrO2Cl2 Q.22 Benzaldehyde  CH3 COONa
  cinnamic acid
Q.16 C6H6  
Dry AlCl
C 6 H 5 C H 3    I
3

CH CHO
‘I’ in the above reaction is obtained by –
3 
C6H5CHO  C6H5CH = CHCOOH (A) CH3COOH + PCl 5
NaOH
(B) CH3CH2OH + K2Cr2O7/H2SO 4
The reactions involved in the above reaction
sequence are – (C) CH3COCl + CH3COONa
(D) CH3CONH2 + P2O 5
(A) Friedel Craft, Gattermann, Aldol
condensation
(B) Friedel Craft, Etard, Claisen condensation Q.23 Aromatic aldehydes undergo disproportionation
(C) Friedel Craf t, Sommlet, Claisen in presence of sodium or potassium hydroxide
condensation to give corresponding alcohol and acid. The
reaction is known as -
(D) Friedel Craft, Sommlet, Aldol
condensation (A) Wurtz reaction
(B) Cannizzaro reaction
Q.17 Replacement of carbonyl oxygen takes place
(C) Friedel-Craft reaction
in the reaction –
(D) Claisen reaction
(A) Benzaldehyde + Hydroxylamine
(B) Benzldehyde + Phenylhydrazine
(C)Benzaldehyde+ Phosphorus pentachloride Q.24 An example of Perkin's reaction is -
(D) In all the above reactions KOH
(A) C6H5CHO + CH3NO 2  
C6H5CH = CHNO2
Q.18 Aromatic aldehydes react with primary
(B) C6H5CHO + CH2(COOH)2
amines to form the following –
Alc.NH3
(A) Urea (B) Amide    C6H5CH=CHCOOH
(C) Schiff’s base (D) Oxime NaOH
(C) C6H5CHO + CH3CHO  
Q.19 Which aldehyde is used in the manufacture C6H5CH = CHCHO
of perfumes – (D) C6H5CHO + (CH3CO)2O
(A) Cinnamaldehyde (B) Benzaldehyde CH COONa
 3  C6H5CH=CHCOOH
(C) Propionaldehyde (D) Acryladehyde

Q.20 Reaction Q.25 The reaction

C6H5COCl + H2  C6H5CHO + HCl ( i) Piperdine
C6H5CHO + H2C(COOH)2   
( ii) H O / 
occurs in the presence of – 2

(A) Zn/HCl (B) AlCl 3 C6H5CH = CHCOOH, is commonly known as

(C) Pd/BaSO4 (D) Ni/Pt (A) Claisen-Schmidt condensation
(B) Perkin reaction
Q.21 Which of the following is not a correct (C) Knoevenagel condensation
statement –
(D) Aldol condensation
(A) Acetophenone does not give a red colour
precipitate with fehling’s solution
(B) Benzaldehyde gives a red coloured
precipitate with Fehling’s solution
(C) Benzaldehyde gives silver mirror with
Tollen’s reagent
(D) Benzaldehyde giv es a black grey
precipitate with mercuric chloride solution
 LEVEL # 3
Q.1 By which of the following sets of reagents can
benzene be formylated to benzaldehyde in the CH2OH CHO
presence of anhydrous AlCl3 ?
(A) HCHO and HCl (B) and
(B) HCOOCH3 and HCl NH2 NH2
(C) CO and HCl
(D) HCONH2 and HCl CHO CH2OH

Q.2 Benzaldehyde on being heated with

acetaldehyde in the presence of aqueous (C) and
NaOH forms– NH2 NH2
(A) crotonaldehyde (B) salicyldehyde
(C) cinnamialdehyde (D) furfuraldehyde CH2OH CHO

Q.3 When calcium benzoate is heated with calcium (D) and

formate, the major product formed is– NH2
NH2
(A) benzaldehyde (B) acetophenone
(C) benzophenone (D) acetaldehyde
Each of the questions given below consist of
Q.4 In the Cannizzaro reaction : Statement – I and Statement – II. Use the
2PhHO OH
– – following Key to choose the appropriate
 PhCH2OH + PhCOO
answer.
the slowest step is–
(A) If both Statement- I and Statement- II are
(A) the attack of the OH– at the carbonyl group
true, and Statement - II is the correct
(B) the transfer of the hydride ion to the carbonyl
group explanation of Statement– I.
(C) the abstraction of proton from the carboxylic (B) If both Statement - I and Statement - II
acid are true but Statement - II is not the
(D) the deprotonation of PhCH2OH correct explanation of Statement – I.
(C) If Statement - I is true but Statement - II
Q.5 Benzaldehyde reacts with an excess of is false.
anhydrous ethyl alochol in the presence of (D) If Statement - I is false but Statement - II
HCl to give– is true.
(A) C6H5COOC2H5 (B) C6H5COCl
(C) C6H5CH(OC2H5)2 (D) C6H5CH2Cl Q.7 Statement I : p-nitrobenzaldehyde is more
Q.6 Consider the following two reactions. reactive than benzaldehyde.
Statement II : Benzaldehyde is less reactive
CHO than acetone.
NaBH4 SnCl2-HCl
A B Q.8 Statement I : Both acetone and
<100ºC
NO2 benzaldehyde are less reactive to nucleophilic
attack as compared to acetaldehyde.
The two major products (A) and (B) are
Statement II : Both acetone and
respectively–
benzaldehyde are resonance stabilized.
CH2OH CHO
Q.9 Statement I : Aldehydes can be easily
(A) and prepared by the reduction of carboxylic acids
NO2 NH2 with LiAlH4.
Statement II : In going from —COOH to
—CHO group oxidation number of C
decreases.
 LEVEL # 4
(Question asked in previous AIEEE & IIT-JEE)

SECTION-A
Q.1 Which one of the following undergoes reaction Q.3 The structure of compound I is-
with 50% sodium hydroxide solution to give Ph CH3
the corresponding alcohol and acid ?
(A)
H Ph
(A) Phenol (B) Benzaldehyde
(C) Butanal (D) Benzoic acid H3C Ph
(B)
SECTION-B H Ph

Ph CH3
Q.1 + X
(C)
H CH2Ph
,
‘X’ is - H3C CH3
(D)
(A) CH3COOH (B) BrCH2  COOH Ph H
|
CHO Q.4 The structures of compounds J, K and L
(C) COOH (CH3CO)2O (D) (CH3CO)2O respectively, are -
(A) PhCOCH3, PhCH2COCH3 and PhCH2COO–K+
Q.2 Compound H is formed by the reaction of - (B) PhCHO, PhCH2CHO and PhCOO–K+
(C) PhCOCH3, PhCH2CHO and CH3COO–K+
O (D) PhCHO, PhCOCH3 and PhCOO–K+

(A) + PhMgBr
Ph CH3

(B) + PhCH2MgBr
Ph CH3

(C) + PhCH2MgBr
Ph H

O Me

(D) +
Ph H Ph MgBr
 ANSWER KEY
LEVEL # 1
Q.No. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20
Ans. A D B C A D B C A C B B B C D A D A A B
Q.No. 21 22 23 24 25
Ans. B D C A B

LEVEL # 2
Q.No. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20
Ans. C C A C B B A A B D C D B C A B D C B C
Q.No. 21 22 23 24 25
Ans. B C B D C

LEVEL # 3
Qus. 1 2 3 4 5 6 7 8 9
Ans. C C B B C A B C D

LEVEL # 4
SECTION-A
Qus. 1
Ans. B

SECTION-B
Qus. 1 2 3 4
Ans. D B A D