16
AtoZ CHEMISTRY Carbonyl Compounds (Aldehyde & Ketone) Rishi Sir [B.Tech. IIT Kanpur] www.atozchemistry.com Be Topper with Topper in Chemistry in JEE Main & JEE-ADV Contact No. +91 9852476717 21 Carbonyl Compounds (Aldehyde & Ketone) 1. Preparation of Carbonyl Compounds Q 1. The major product in the reaction (A) (B) (C) (D) None of these Q 2. The product in the reaction (A) (B) (C) (D) Q 3. The product in the reaction (A) (B) (C) (D) None of these Q 4. The reduction of R-COOH to RCHO is difficult because (A) RCHO is better reducing agent (B) RCOOH is better reducing agent (C) Attack of H on R-COOH is easier compare to RCHO (D) Attack of H on R-CHO is easier compare to R-COOH Q 5. To reduce 3 R COOCH into RCHO, Reducing agent is (A) 4 LiAlH (B) 3 Li t BuO AlH (C) 3 Li t BuO AlH (D) LiH Q 6. In which of the following molecule electrophile & Nucleophile Attack on same position (A) RCN (B) RNC (C) (D) RmgX Q 7. The product on the reaction (A) (B) (C) (D) Both B & C Q 8. In the reaction HO 3 3 CH NC Phli Product, is (A) 3 2 CH NH PhCN (B) (C) (D) Q 9. Among the following compounds, the one which will produce ethyl methyl ketone on oxidation is (A) isobutyl alcohol (B) s-butyl alcohol (C) t-butyl alcohol (D) isopropyl alcohol Q 10. Which of the following on hydrolysis with aqueous KOH gives acetaldehyde ? (A) Ethylene chloride (B) Ethylidene chloride (C) Ethyl chloride (D) Acethylene dichloride Q 11. Calcium acetate on strong heating produces (A) diethyl ketone (B) dimethyl ketone H – C – OH + Ph – C – OH O O CaO / H – C – H O Ph – C – Ph O Ph – C – H O O O OH HO 1. CaO 2. O O O O C – OH HO O CH 3 O 1. CaO 2. CH 3 O CH 3 O H 3 C O R – C – OH O CH – C – C H 3 2 5 NH H / HO + 2 CH – C – C H 3 2 5 O CH – C – NH 3 5 O CH 2 5 – C – NH 2 O CH NH +Ph – C – CH 3 2 3 O CH NH + Ph – C – C–H 3 2 O Ph – C – NH 2 O

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Page 1: Carbonyl Compounds (Aldehyde & Ketone) · 2020. 11. 3. · Carbonyl Compounds (Aldehyde & Ketone) 1. Preparation of Carbonyl Compounds Q 1. The major product in the reaction H (A)

AtoZ CHEMISTRY Carbonyl Compounds (Aldehyde & Ketone)

Rishi Sir [B.Tech. IIT Kanpur] www.atozchemistry.com Be Topper with Topper in Chemistry in JEE Main & JEE-ADV Contact No. +91 9852476717

21

Carbonyl Compounds (Aldehyde & Ketone)

1. Preparation of Carbonyl Compounds

Q 1. The major product in the reaction

(A) (B)

(C) (D) None of these

Q 2. The product in the reaction

(A) (B)

(C) (D)

Q 3. The product in the reaction

(A) (B)

(C) (D) None of these

Q 4. The reduction of R-COOH to R–CHO is difficult

because

(A) R–CHO is better reducing agent

(B) R–COOH is better reducing agent

(C) Attack of H on R-COOH is easier compare

to R–CHO

(D) Attack of H on R-CHO is easier compare

to R-COOH

Q 5. To reduce 3R COOCH into R–CHO,

Reducing agent is

(A) 4LiAlH

(B) 3Li t BuO AlH

(C) 3Li t BuO AlH (D) LiH

Q 6. In which of the following molecule electrophile

& Nucleophile Attack on same position

(A) R–CN (B) R–NC

(C) (D) RmgX

Q 7. The product on the reaction

(A) (B)

(C) (D) Both B & C

Q 8. In the reaction

H O3

3CH NC Phli

Product, is

(A) 3 2CH NH PhCN

(B)

(C)

(D)

Q 9. Among the following compounds, the one which

will produce ethyl methyl ketone on oxidation is

(A) isobutyl alcohol (B) s-butyl alcohol

(C) t-butyl alcohol (D) isopropyl alcohol

Q 10. Which of the following on hydrolysis with

aqueous KOH gives acetaldehyde ?

(A) Ethylene chloride

(B) Ethylidene chloride

(C) Ethyl chloride

(D) Acethylene dichloride

Q 11. Calcium acetate on strong heating produces

(A) diethyl ketone (B) dimethyl ketone

H – C – OH + Ph – C – OH

O O

CaO /

H – C – H

O

Ph – C – Ph

O

Ph – C – H

O

O

O

OH

HO1. CaO

2.

OO

OO

C – OH

HO

O CH3

O

1. CaO

2.

CH3

O CH3

O

H3C O

R – C – OH

O

CH – C – C H3 2 5

NHH / H O

+

2

CH – C – C H3 2 5

O

CH – C – NH3 5

O

C H2 5 – C – NH2

O

CH NH +Ph – C – CH3 2 3

O

CH NH + Ph – C – C–H3 2

O

Ph – C – NH2

O

Page 2: Carbonyl Compounds (Aldehyde & Ketone) · 2020. 11. 3. · Carbonyl Compounds (Aldehyde & Ketone) 1. Preparation of Carbonyl Compounds Q 1. The major product in the reaction H (A)

AtoZ CHEMISTRY Carbonyl Compounds (Aldehyde & Ketone)

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(C) acetaldehyde (D) formaldehyde

Q 12. Consider the following sequence of reactions

The product (B) is

(A) 3 3CH COOCH (B) 3 3CH CHOHCH

(C) 3 3CH COCH (D) 3CH COOH

Q 13. Consider the following reaction sequence

The final product (B) is

(A) 3 2 2 2CH CH CH NH

(B) 3 2 2CH CH CONH

(C) 3 2CH CH CHO

(D) 3 2CH CH COOH

Q 14. Identify the final product formed in the following

sequence of reactions ?

(A) (B)

(C) (D)

Q 15.

The principal organic product is

(A)

(B)

(C)

(D)

Q 16. In the following reacton,

A and B are

(A)

(B)

(C)

(D)

Q 17. In the given reaction

(A) and (B) respectively be

(A) 3CH CHO and 3CH CHO

(B) 3 3CH COCH and 3CH CHO

(C) 3 3CH COCH and 3 3CH COCH

(D) 3CH COOH and 3 3CH COCH

Q 18. An organic compound on treatment with 4HIO

gives cyclopentanone and formaldehyde. The

compound is

Page 3: Carbonyl Compounds (Aldehyde & Ketone) · 2020. 11. 3. · Carbonyl Compounds (Aldehyde & Ketone) 1. Preparation of Carbonyl Compounds Q 1. The major product in the reaction H (A)

AtoZ CHEMISTRY Carbonyl Compounds (Aldehyde & Ketone)

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(A)

(B)

(C)

(D)

Q 19. The product formed in the oxidation reaction

(A)

(B)

(C)

(D) None of these

Q 20. In above problem, mole of 4HIO required per

mole of reactant is

(A) 1 (B) 2 (C) 3 (D) 4

2. Physical & Chemical Properties of Carbonyl

Compounds, Beckman Rearragement

Q 1. B.P. of aldehyde & ketone is less than that of

(A) Alcohol (B) Acid

(C) Alkene (D) Both A & B

Q 2. The correct order of reactivity of PhMgBr with

(A) I II III (B) III II I

(C) II III I (D) I III II

Q 3. The formation of cyanohydrins from a ketone is

an example of

(A) nucleophilic substitution

(B) electrophilic substitution

(C) electrophilic addition

(D) nucleophilic addition

Q 4. A cyanohydrins of a compound (X) on hydrolysis

gives an hydroxyl acid which shows optical

activity after resolution. The compound (X) is

(A) Acetone (B) Formaldehyde

(C) Diethyl ketone (D) Acetaldehyde

Q 5.

D is

(A) (B)

(C) (D)

Q 6. The eqK . Values in HCN addition to following

aldehydes are in the order

(A) I II III (B) II III I

(C) III I II (D) II I III

Q 7. Consider the following sequence of reactions

CH OH2

C = O

CH2

CH – OH

CH OH2

HIO4

H – C – C – C – H, CH – C – H, H CHO3

OOOO

H – C – C – CH , 2CH = 03 2

O O

HCHO, H– C – CH – C – H , HCHO2

OO

Page 4: Carbonyl Compounds (Aldehyde & Ketone) · 2020. 11. 3. · Carbonyl Compounds (Aldehyde & Ketone) 1. Preparation of Carbonyl Compounds Q 1. The major product in the reaction H (A)

AtoZ CHEMISTRY Carbonyl Compounds (Aldehyde & Ketone)

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The products (A) and (B) are, respectively

(A)

(B)

(C)

(D)

Q 8. 2 2 2CH CHO NH OH CH CH N OH

The above reaction occurs satisfactorily at

(A) pH = 1 (B) pH = 4.5

(C) pH = 12 (D) Any value of pH

Q 9. Pentan -2-one

2 2

4

NH OH TsCl H O

NH ClA

Product

The final product(s) formed in the above reaction

(A) N-propyl ethanamide

(B) N-methyl propanamide

(C) Both

(D) None

Q 10. In the reaction sequence

2 52 2P O /NH OH/ H H O/ H

6 5C H CHO X Y Z

[X], [Y] and [Z] respectively be

(A) 6 5 5 6 5 6 5C H CH N OH,C H CN,C H COOH

(B) 6 5 5 6 5 2 6 5C H CH NOH,C H CONH ,C H COOH

(C) 6 5 2 6 5 6 5 2C H CH NHOH,C H COOH,C H COONH

(D) 6 5 2 6 5 6 5C H CH NHOH,C H COOH,C H CN

Q 11. An optically active compounds (X) reacts with

phenyl hydrazine to form phenylhydrazone

derivative. The compound X, gives a yellow

precipitate of iodoform with I2 and NaOH. The

compound x is

(A)

3 2 2 3CH CH CCH CH

O

(B)

(C)

(D)

Q 12. Predict the products of the following reactions

(i)

(ii)

(iii)

(iv)

Q 13. In the reaction

The product formed will be

(A) C6H5NHCOCH2CH3

O

HOCH . CH OH2 2

H+

COOCH3

A1. LiAlH . Et O4 2

2. H O2

+

OO

C – OCH3

O

and

OH

COOCH3

OO

COOCH3

and

O

CHO

OO

COOCH3

and

O

CH OH2

COOCH3

and

OCH = CH2

CH OH2

HO OCH CH OH2 2

O

3 2 3CH CCH CH CH

CH3

O CH3

3 2 3CH C CH CH CH

3 2

CH CH CCH

OCH3

O

+ HO – NH2

H+

O

+ NH – NH2

O N2

NO2

R – CH = CH – CHO + NH – C – NH – NH2 2

OH

+

C

O

CH3 + CH CH NH3 2 2

H+

Page 5: Carbonyl Compounds (Aldehyde & Ketone) · 2020. 11. 3. · Carbonyl Compounds (Aldehyde & Ketone) 1. Preparation of Carbonyl Compounds Q 1. The major product in the reaction H (A)

AtoZ CHEMISTRY Carbonyl Compounds (Aldehyde & Ketone)

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(B) C6H5CONHCH2CH3

(C) C6H5CN (D) CH3CH2CN

Q 14. In the reaction,

Q 15. In the reaction

H / H O2

Product, is

(A)

(B)

(C) Both A & B

(D) None of these

Q 16. In the reaction

H / H O2

3CH CH NH OH

product

is

(A) (B)

(C) 3CH CN (D) None of these

3. The witting Reaction, Schmidt Reaction,

Bayer – villigar oxidation

1. In the reaction

Product, is

(A)

(B)

(C)

(D) None of these

Q 2. Propose a suitable mechanism for these reaction.

(i)

CH3-CH-CH2-CH2-CH2-CHO

OH

CH3OH/H

O

OCH3

CH3

+

(ii) Ph Mg Br + 2Ph CHO

1.Et2O

2.H2OPh Ph + PhCH2

OH

O

Q 3. In the reaction

PhCH Br PPh2 3Ph CHO

Product, is

(A) Ph CH C O

(B) Ph CH CH Ph

(C) 2Ph CH CH

(D) 3 2Ph PBr

Q 4. The correct way to represent witting reagent is

(A) 3 2Ph P CH (B) 3 3Ph P CH I

(C) 3 2Ph P CH

(D) 3 2Ph P CH

Q 5. In the reaction,

CCH3

Ph

N

OH

O

CH – C – NH – Ph3

O

Ph – C – NHCH3

CH – C – NH3 2

O

H – C – NH – CH3

O

C = OCH3

C H2 5

1. Ph P, CH I3 3

C = CH2

CH3

C H2 5

C = C = O

CH3

C H2 5

CH – CH3

CH3

CH3

Page 6: Carbonyl Compounds (Aldehyde & Ketone) · 2020. 11. 3. · Carbonyl Compounds (Aldehyde & Ketone) 1. Preparation of Carbonyl Compounds Q 1. The major product in the reaction H (A)

AtoZ CHEMISTRY Carbonyl Compounds (Aldehyde & Ketone)

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Product, is

(A)

(B)

(C)

(D) None of thee

Q 6. In the reaction

Product, is

(A) (B)

(C) (D)

Q 7. In the reaction

Product is

(A) (B)

(C) (D)

Q 8. In the reaction

Product, is

(A) 3 2CH NH (B) 3CH CH

(C) (D) 3CH NC

Q 9. In the reaction

Product, is

(A) Ph CN (B) 2 2PhCH NH

(C) Ph N C O (D) None of these

Q 10. The major product of following reaction is

(A) (B)

(C) (D) None of these

Q 11. In the reaction

Product, is

(A) (B)

(C) (D)

Q 12. Consider the given reaction

The above reaction is known as

(A) Baeyer – villager oxidation

(B) Oppenaur oxidation

(C) Periodate oxidation

(D) Peroxide oxidation

Q 13. Product is

CH – C – C H3 2 3

OHN3

H+

CH – C – NH – C H 3 2 5

O

C H CH2 5 3 – C – NH –

O

CH – C – C H3 2 5

N

N+

N–

Ph – C – CH3

OHN3

H+

Ph – C – NH – CH3

O

CH – C – N3 3

O

Ph – C – N3

O

CH – C – NH – Ph3

O

Ph – C – H

OHN3

H+

Ph – C – NH2

O

H – C – NH – Ph

O

H – C – NH2

O

Ph – C N

CH – C – OH3

OHN /H3

+

Ag O, H O2 2

CH – C – N3 3

O

Ph – C – OH

OHN /H3

+

Ag O2

CH – C – Ph3

OCH CO H/H3 3

+

CH – C – OPh3

O

Ph – C – OCH3

O

Ph – C – OPh

O

CH – C – OCH3 3

O

Page 7: Carbonyl Compounds (Aldehyde & Ketone) · 2020. 11. 3. · Carbonyl Compounds (Aldehyde & Ketone) 1. Preparation of Carbonyl Compounds Q 1. The major product in the reaction H (A)

AtoZ CHEMISTRY Carbonyl Compounds (Aldehyde & Ketone)

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(A) (B)

(C) (D)

Q 14. In the reaction

O

CH311

18 183 /H

O

CH C O O H Product, is

(A) (B)

(C) (D)

Q 15. Write products in following sequence of

reactions

CH3O C-CH3 CH3O-CH=PPh3

?H3O+

H2O ?

O

+

4. Aldol Condensation Reaction

Q 1. In condensation reaction

(A) larger molecules combine together

(B) Smaller molecules combine together

(C) Larger molecules combine together with

elimination of smaller molecules

(D) smaller molecular combine together with

elimination of larger molecules

Q 2. Aldol condensation is possible under

(A) Acidic condition (B) Basic condition

(C) Both A & B (D) Strong acidic condition

Q 3. The product in the reaction

Product, is

(A)

(B)

(C)

(D) None of these

Q 4. The product in the reaction

Product, is

(A)

(B)

(C)

(D) None of these

Q 5. The product in the reaction

Product, is

(A) (B)

O

CH3

O

CH – CO – CH3 3

K CO2 3

C = CH – C – CH3

OCH3

CH3

CH – CH = CH – C – CH3 3

O

CH – C – CH – CH3 2

O

CH – CH – C – CH3 2 3

O1. H

+

2.

C = CH – C – C H2 5

C H2 5

CH3

O

CH – C – C = C 3

C H2 5

CH3

CH3

O

C H2 5

CH3

C = CH – C – CH3

O

O + HCHOK CO2 3

CH2

CH2

O

O CH 3

18O

O

CH 3

O18

O

CH 3

O

Page 8: Carbonyl Compounds (Aldehyde & Ketone) · 2020. 11. 3. · Carbonyl Compounds (Aldehyde & Ketone) 1. Preparation of Carbonyl Compounds Q 1. The major product in the reaction H (A)

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(C) (D)

Q 6. The product in the reaction

product, is

(A)

(B)

(C)

(D)

Q 7. Which one of the following compounds on

heating with a base gives as the

final product ?

(A)

(B)

(C)

(D)

Q 8. What is the product (A) of following reaction?

(A) (B)

(C) (D)

Q 9. NaOH,

aldol

A, A can be

(A) (B)

(C) (D)

Q 10. Write structures of the Products.

C

CH2-CH2-CHO

O

H Aq.NaOH?

Aq.K2CO3?

Q 11. Write the aldol product of the following reaction

(i) PhCHO with CH3NO2 in presence of OH–

(ii) PHCHO with CH3C≡N in presence of OH–

(iii) Me2CO with CHCl3 in presence of OH–

(iv) Me2CO with CH3C≡CH in presence of 2NH

(v) Me2CO with in presence of OH–

(vi) Ph2CO with Ph2CH2 in persnce of 2NH

(vii)

– 3 2

3 6 4 3 2 2

 

CH CH COO Na

P CH C H CHO CH CH CO O

CH2

O

CH2

O

CH3

O

K CO2 3

O

OCH3

OO

O O

O

OH/

Q

(A)

O

O

O

O

O

O

O

O

O

O

O

CH 3

O

Page 9: Carbonyl Compounds (Aldehyde & Ketone) · 2020. 11. 3. · Carbonyl Compounds (Aldehyde & Ketone) 1. Preparation of Carbonyl Compounds Q 1. The major product in the reaction H (A)

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(viii) –

6 5 6 5 2       OH

C H CHO C H CH C N

(ix) –

3 3 6 5        2     OH

CH COCH C H CHO

(x) =O + –

2 3  OH

N CCH COOCH

Q 12. PhCHO and CH3COCH2CH3 give

PhCH=CHCOCH2CH3 in basic Medium and

PhCH=C(CH3)COCH3 in acidic medium. Give a

mechanistic explanation.

Q 13.

Product, is

(A)

(B)

(C)

(D) None of these

5. Cannizaro Reaction

Q 1. Which of the following is a disproportionation

reaction ?

(A) Aldol condensation reaction

(B) Cannizaro reaction

(C) Witting reaction

(D) Bayer villegar oxidation

Q 2. In the Cannizzarro reaction given below,

2PhCHO PhCH2OH+PhCO2-,

the slowest step is

(A) the attack of –OH at the carbonyl group

(B) the transfer of hydride to the carbonyl group

(C) the abstraction of proton from carboxylic acid

(D) the deprotonation of PhCH2OH.

Q 3. The correct order of H donation by following

molecule is

(A) I II III (B) I II III

(C) II III I (D) III II I

Q 4. In the Cannizzaro reaction, the intermediate that

will be the best hydride donor is

(A)

(B)

(C)

(D)

Q 5. The product in the reaction

OHPhCHO HCHO

Products, are

(A) 2PhCH OH HCOO

(B) 3PhCOO CH OH

(C) Ph CH CH CH CHIO

(D) None of these

Q 6. At high constant of OH, connizaro reaction is a

(A) 3rd order reaction (B) 2nd order reaction

(C) 4th order reaction (D) can’t predict

Q 7. Which of the following molecules doesn’t

undergo cannizaro reaction ?

(A) Ph CHO (B) 3P Me N PhCHO

(C) 3CH CHO (D) Both B & C

O

OH / –

CH – C 3 C – CH3

O O

CH – C 3H

OO

C

OH

H

H

I

C

H

H

II

C

H

CH3

III

C

HO¯

CH O3

C

HO¯

C

HO¯

OH

C

HO¯

O N2

O OH

Page 10: Carbonyl Compounds (Aldehyde & Ketone) · 2020. 11. 3. · Carbonyl Compounds (Aldehyde & Ketone) 1. Preparation of Carbonyl Compounds Q 1. The major product in the reaction H (A)

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Q 8. The product in the reaction

3CH CHO 3HCHO Ca OH

2 A

HCHO NaOHA

Product, is

(A) 2 3HC CH OH (B) 2 4

C CH OH

(C) 4C CHO (D) 2 3C CH OH CH

Q 9. Phenylglyoxal, 6 5C H COCHO , on heating with

concentrated NaOH gives

(A) 6 5C H COONa and 3CH OH

(B) 6 5 2C H CH OH and HCOONa

(C) 6 5C H CHOHCOONa

(D) 5 5C H COONa and HCOONa

Q 10. The reaction heat

conc. NaOH produces

(A) (B)

(C) (D)

Q 11.

In the reaction

The product (X) is

(A)

(B)

(C)

(D)

Q 12. Predict the product in the following reaction

product

(A) (B)

(C) (D)

Q 13. Which of following will not undergo Cannizaro

Reaction?

(A) (B)

(C) (D) 3Cl C CHO

Q 14. Product (B)

is

(A) (B)

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(C) (D) 2H C C O

Q 15. X and Y

(Y is alcohol, D is deuterium)

X and Y will have structure

(A)

(B)

(C)

(D) None of these are correct.

Q 16. By Canninzzaro reaction A changes to B and C as

given

Thus, A is

(A) (B)

(C) (D)

Q 17.

CHO OHC

CHO OHC

(I) NaOH/1000C(II) H+/H2O

Major product is

Q 18. What are the products of the crossed-Cannizzaro

reaction of

(i) H2CO and PhCHO

(ii) H2CO and Me3CCHO?

(iii) PhCOCHO and PhCOCHCl2

6. Clasien condensation, Benzoin condensation,

Reformastky reaction

Q 1. In the reaction

Product is

(A)

(B)

(C)

(D) None of these

Q 2.

What is X ?

(A) 3CH COOH (B) 2BrCH COOH

(C) 3 2CH CO O (D) CHO COOH

Q 3. The product of the reaction:

2CH – C3

OC H2 5

O1. C H ONa2 5

2. H+

CH – C – C H3 2 5

O

CH – C – CH3 2 – C – OH

O O

CH – C – CH3 2 2 5– C – OC H

O O

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Will be

(A) 6 5C H CH CH COOH

(B)

(C)

(D)

Q 4.

The compound (X) is

(A) 3CH COOH (B) 2BrCH COOH

(C) 3 2CH CO O (D) CHO COOH

Q 5. The product in the reaction Product, is

(A) (B)

(C) (D) None of these

Q 6. In the reaction

Product,

is

(A) (B)

(C) (D)

Q 7. In the reaction

Product, is

(A)

(B)

(C)

(D) None of these

Q 8. In the reaction

Product, is

(A)

(B)

(C)

(D) None of these

Q 9. The given reaction

is known as

(A) Perkin reaction

(B) Knoevenagel reaction

O

+

COOC H2 5

COOC H2 5

1. C H ONa 2. H2 5

+

3.

OC – COOH

OO

COOC H2 5

OC – COOC H2 5

O

C – H

O

1. KCN, CH OH3

2. H O/HCl2

C – CN

O

CH – CN

OH

CH

OH

C – CH

O

OH

C – H

O

+ CH NO3 2

KOH

–H O2

CH = CH – NO2

CH – CH – NO2 2

OH

CH = CH – CHO

O+ (CH CO) O, ACONa3 2

OCH - CH2

OCH = CH – COOH

OCOOH

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(C) Reformatsky reaction

(D) Claisen – Schmidt reaction

Q 10. In the reaction

Product, is

(A)

(B)

(C)

(D)

Q 11. In the given reaction

[X] will be

(A) (B)

(C) (D)

Q 12. 2PhCOCH on reaction with 2SeO gives

(A) PhCOOH and 2PhCH COOH

(B) 2 2PhCH CH Ph

(C) PhCHOHCHOHPh

(D) PhCOCOPh

Q 13. In the reaction sequence

The product (B) is

(A) (B)

(C) (D)

7. Tests of Aldehyde & Ketone

Q 1. In DNP test, when ArCHO reacts with

the precipitate

obtained is

(A) Yellow (B) Blue

(C) Red (D) Orange

Q 2. Which of the following doesn’t respond to

fehling’s solution test

(A) (B) Ph – CHO

(C) 2H CHO (D) Both A & B

Q 3. Which of the following doesn’t respond to

tollen’s reagent test ?

(A) Ph CHO (B) 3 3H C CO CH

(C) 2H CHO (D) All of these

Q 4. The schiff’s reagent is

(A)

(B)

(C)

Ph – C – CH + CH – C – OC H3 2 2 5

O O1. Zn

2. H O2

Br

Ph – C – CH = CH – COOEt

O

C = CH – COOEtPh

CH3

Ph – C – CH - CH – COOH

O

C = CH – COOHPh

CH3

NO2

H N – NH2 NO2

CH – C – CH3 2 5

O

Cl¯ H N3+

C

NH2

NH2

Cl¯ H N3+

C

NH2

NH2

Cl¯ H N 3 +

C NH 2

CH 3

NH 2

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(D)

Q 5. Which of the following doesn’t respond to

schiff’s reagent test ?

(A) (B) 3CH CHO

(C) (D) All of these

Q 6. In schiff’s reagent test, colom change ocur as

(A) Red blue red

(B) Red colourless

(C) Red Colourless green

(D) Red Colourless Red

Q 7. Which of the following doesn’t respond to

sodium nitropruside test ?

(A) 3CH CHO (B) HCHO

(C) ArCHO (D)

Q 8. An organic compound A, C6H10O. On reaction

with CH3MgBr followed by acid treatment gives

compound B. The compound B on ozonolysis

gives compound C, which in the presence of a

base gives 1-acetyl cyclopentene D. The

compound B on reaction with HBr gives

compound E. Write the structures of A, B, C, and

E. Show how D is formed by C.

Q 9. An alkene (A) on ozonolysis yields acetone and

an aldehyde. The aldehyde is easily oxidized to

an acid (B). When B is treated with bromine in

presence of phosphorous it yields a compound

(C) which on hydrolysis gives a hydroxyl acid

(D). This acid can also be obtained from acetone

by the reaction with hydrogen cyanide followed

by hydrolysis. Identify the compounds A, B, C

and D. [IIT JEE 1982]

Q 10. A hydrocarbon A (M.F. C5H10) yields 2-

methylbutane on catalytic hydrogenation. A adds

HBr (in accordance with Markownkoff,s rule) to

form a compound B which on reaction with silver

hydroxide forms an alcohol C, C5H12O. Alcohol

C on oxidation gives a ketone D. Deduce the

structures of A, B, C and D and show the reaction

involved. [IIT JEE 1988]

Q 11. A ketone A which undergoes haloform reaction

gives compound B on reduction. B on heating

with sulphuric acid gives compound C, which

forms mon ozonide D. D on hydrolysis in

presence of zinc dust gives only acetaldehyde.

Identify A, B and C. Write down the reactions

involved. [IIT JEE 1989]

Q 12. An organic compound A, C8H6, on treatment with

dilute sulphuric acid containing mercuric

sulphate gives a compound B, which can also be

obtained from a reaction of benzene with an acid

chloride in the presence of anhydrous aluminium

chloride. The compound B, when treated with

iodine in aqueous KOH, yields C and a yellow

compound D. Identify A, B, C and D with

justification. Show how B is formed from A.

[IIT JEE 1994]

Q 13. An aldehyde A(C11H8O), which does not undergo

self aldol condensation, gives benzaldehyde and

two moles of B on ozonolysis. Compound B, on

oxidation with silver ion gives oxalic acid.

Identify the compounds A & B. [IIT JEE 1998]

H N2 C

Ph – NH2

Ph – CH3

CHO

OH

CHO

CH – C – CH3 2 5

O

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Answer Key

1. Preparation of Carbonyl Compounds

(1). C (2). A (3). C

(4). D (5). B (6). B

(7). A (8). C (9). B

(10). B (11). B (12). C

(13). C (14). D (15). B

(16). C (17). B (18). C

(19). C (20). B

2. Physical & Chemical Properties of Carbonyl

Compounds, Beckman Rearragement

(1). D (2). C (3). D

(4). D (5). A (6). D

(7). C (8). B (9). A

(10). A (11). C

(12).

(i)

(ii)

(iii)

(iv)

(13). B (14). C (15). B

(16). C

3. The witting Reaction, Schmidt Reaction,

Bayer – villigar oxidation

(1). A (2). See the Notes

(3). B (4). D (5). A

(6). D (7). D (8). B

(9). C (10). A (11). A

(12). A (13). D (14). C

(15).

4. Aldol Condensation Reaction

(1). C (2). C (3). A

(4). B (5). B (6). C

(7). A (8). B (9). A

(10).

(11).

(i) 2Ph CH CH NO

(ii) Ph CH CH CN

(iii) (iv)

(v) (vi)

(vii)

(viii)

(ix)

(x)

NH – OH

NH – NH

NO2

NO2

R – CH = CH – C = NH – NH – C – NH2

O

H C3

C = NH – CH – CH2 3

CH O3

C = CH – OCH3

CH3

CH O3

CH = CH = O

CH3

CHO O

C = CCl2

CH3

CH3

C = C = Cl2

CH3

CH3

Me C2

Ph C = CPh2 2

P – CH – C H – CH = C3 6 4

CH3

O – C – OH

O

C H – CH = C6 5

CN

C H6 5

C H – CH = CH – C – CH = CH – CH6 5 6 5

O

C

CN

COOH

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(12). See the Notes (13). B

5. Cannizaro Reaction

(1). B (2). B (3). C

(4). A (5). A (6). C

(7). D (8). B (9). C

(10). C (11). C (12). A

(13). D (14). B (15). A

(16). A (17). C

(18). (i)

(ii)

(iii)

6. Clasien condensation, Benzoin condensation,

Reformastky reaction

(1). C (2). C (3). D

(4). C (5). B (6). D

(7). A (8). B (9). C

(10). B (11). B (12). D

(13). B

7. Tests of Aldehyde & Ketone

(1). A (2). D (3). B

(4). B (5). C (6). D

(7). B, C

8.

9.

10.

11.

12.

13.

H – C – OH + PhCHOH2

O

H – C – OH + MeC – CHOH3

O

Ph – C – C – OH + Ph – CH – CHCl2

O O OH

O

(A)

CH3

(B)

C

CH3

O

H – C

O

(C)

C – CH3

O

(D)

CH3

Br

(E)

C = CH – CHCH3

CH3

CH3

CH3

(A)

CH3 – CH – COOH

CH3

(B)

CH – C – C – OH3

OBr

CH3

(C)

CH – C – COOH3

OH

CH3

(D)

CH – CH – CH = CH3 2

CH3 CH – CH – CH – CH

3 2

CH3

Br

CH – CH – CH – CH3 2

CH3

OH

CH – CH – C – CH3 2

CH3

O

CH – C – CH – CH3 2 3

O

(A)

CH – CH – CH – CH3 2 3

O

(B)

CH – CH – CH – CH3 3

(C)

CH – CH – CH – CH3 3

O O

O

(D)

C CH

(A)

C – CH3

O

(B)

C – O¯K+

O

(C)

CHI3

(D)

C = Ch – C C – CHO

(A)

CHO

COOH

(B)