Carbonyl Compound I
Carbonyl Compound I
Carbonyl Compound I
EXERCISE-I
O
–
1.
OH
(P) major product
H O 2
O
Structure of (P) is
OH OH
(A) (B) OH (C) (D)
|| O
O O O
(x) OH
2. dil . NaOH (x) is
C – CH3
O
O O O
(A) O (B)
O O
(C) (D)
O O
–
(x) can't be
O
O
(A) (B) O
O
O
O O ||
(C) (D) H – C – H
O
4. O (P) major product
dil . KOH
OH
OH
OH
(A) (B) C – CH3 (C) H3C (D) None
||
O OHC
O
dil .KOH
5. (x) major product
O O
structure of (x) is
O O OH
OH CHO CHO CHO
(A) (B) (C) (D)
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O
15. Total number of intramolecular aldol condensation products possible from given compound is (excluding
stereoisomer).
O O
H
(A) 1 (B) 2 (C) 3 (D) 4
O O
16. Product
(i ) Dil NaOH
(ii)
Compound (A) is :
O OCH3
O
(A) (B) CH3 – C – C – CH3
CH3 – C – CH2 – CH3
OCH3
O O
(C) CH3 – C – CH2 – CH – OCH3 (D) H – C – CH2 – CH2 – CH – OCH3
OCH3 OCH3
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OH
Ph – CH = O
(B)
KOH,
(C) (D)
Ph
Positive
(A)
tollen's test
24.
Ph – CH = O
(B)
Product (B) is
O
CH 3
CH – Ph
(A) Ph – CH = C – CH3 (B) (C) Ph – C = CH – Ph (D) Ph–CH=CH–CH=O
CH3
27. Arrange these compounds in decreasing order of reactivity for the nucleophilic addition reaction :
(I) Acid chloride (II) Aldehyde (III) Ketone (IV) Ester
Select the correct answer from the codes given below:
(A) I > II > III > IV (B) IV > III > II > I (C) III > II > I > IV (D) I > IV > II > III
28. Acetal or ketal is:
(A) Vic dialkoxy compound (B) , -dialkoxy compound
(C) -alkoxy alcohol (D) Gem dialkoxy compound
O
29. P2O5
Ph – C – NH2 ( A )
Product (A) is
(A) Ph – N C (B) Ph – C N (C) Ph – CH2 – NH2 (D) Ph – CH = NH
NH OH / H
30. In the given reaction: C 6H5 C H 2 [X] , [X] will be:
||
O
(A) Only syn oxime (B) Only anti oxime
(C) Mixture of syn and anti oxime (D) Secondary amide
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O
||
50% KOH
38. D – C – D Order of the reaction is :
(A) 2 (B) 3 (C) 4 (D) 1
OH
|
X+Y NaOH
CH3 CH CH CHO
5C |
CH3
CH3
|
(C) CH3–CHO and CH3–CHO (D) CH3–CHO and CH3 C CHO
|
CH3
40. Total number of products in the given reaction :(excluding stereoisomers)
OCH3 OCH3
CO2H H3O
41. (A)
(B)
Product (B) is
OH O OH OH
O
(A) (B) (C) (D)
[X]
will be :
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O NaH, CH3I (P)
53.
LDA, CH3I
(Q)
Product (P) and (Q) respectively is :
O O O O
(A) (B)
O O O O
(C) (D)
Cl
O=S=O
18 –
55. CH3 OH + (A)
CH3O
(B)
CH3
Product (B) is
O O
18
(A) CH3–O–S CH3 (B) CH3–O–S CH3
O O
18
(C) CH3–O–CH3 (D) CH3–O–CH3
O
KOH ||
56. A
KOH – +
B Ph–CH2OH + Ph – CO2K
When A reacts with B in presence of KOH / product C is formed.
Product C is?
O
||
(A) Ph – CH = CH – CHO (B) Ph – CH2 – CH2 – C – CH 3
O
||
(C) Ph – CH = CH – C – CH3 (D) None
57. H
Ph – CH = O + NH2 – NH2 (A). Product (A) is known as :
(A) Aldo-Oxime (B) Hydrazone (C) Hydrate (D) Phenyl hydrazone
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Comprehansion : (Q.64 to Q.66) :
0
Aldehydes and ketones react with one molecule of an alcohol to form compounds called hemiacetals, in
which there is one hydroxyl group and one ether-like group. Reaction of a hemiacetal with a second molecule
of alcohol gives an acetal and a molecule of water. We study this reaction
ROH OH ROH OR
O + +
H OR H OR
Draw structural formulas for the hemiacetal and acetal formed from these reagents. The stoichiometry of
each reaction is given in the problem.
H H
(A) O + 2 CH3CH2OH
(P) (B) O + HOCH2CH2OH
(R)
OH O
H
(C) +
(Q)
OH Acetone
cis-1,2-Cyclohexanediol
O O
(A) (B) (C) (D)
O O
O
O
(A) (B) O (C) (D)
O
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12. Which of the following compounds can undergoes haloform reaction?
O
O
|| ||
O C
|| C–CH2–CH3
(A) CH3–C–CH2–CH2–CH3 (B) (C) (D) CH3 – CH2 – CHO
13. The increasing order of the rate of HCN addition to compounds A – D is [AIEEE-2006]
(I) HCHO (II) CH3COCH3 (III) PhCOCH3 (IV) PhCOPh
(A) I > II > III > IV (B) II > I > III > IV (C) III > IV > I > II (D) IV < III < II < I
14. Among the following the one that gives positive iodoform test upon reaction with I2 and NaOH is
[AIEEE-2006]
CH3
(A) CH3CH2CH(OH)CH2CH3 (B) C6H5CH2CH2OH (C) H3C (D) PhCHOHCH3
OH
..
In Cannizzaro reaction given below , 2 Ph CHO Ph CH2OH + Ph CO
:OH
15. 2 the slowest step is :
16. Trichloroacetaldehyde was subjected to Cannizzaro's reaction by using NaOH. The mixture of the products
contains sodium trichloroacetate ion and another compound. The other compound is : [AIEEE-2011]
(A) 2,2,2-Trichloroethanol (B) Trichloromethanol
(C) 2,2,2-Trichloropropanol (D) Chloroform
17. Sodium ethoxide has reacted with ethanoyl chloride. The compound that is produced in the above reaction is:
[AIEEE-2011]
(A) Diethyl ether (B) 2-Butanone (C) Ethyl chloride (D) Ethyl ethanoate
18. Silver Mirror test is given by which one of the following compounds ? [AIEEE-2011]
(A) Acetaldehyde (B) Acetone (C) Formaldehyde (D) Benzophenone
(A) Ethyl methyl ketone (B) Isopropyl alcohol (C) 3-Methyl-2-butanone (D) Isobutyl alcohol
20. In the given transformation, which the following is the most appropriate reagent ? [AIEEE-2012]
CH = CHCOCH3
Re agent
HO
CH = CHCH2CH3
HO
(A) NH 2NH 2, OH (B) Zn–Hg/HCl (C) Na, Liq, NH3 (D) NaBH4
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32. Which one of the following reactions will not result in the formation of carbon bond ?
[IIT Mains Online 2014]
(A) Reimer-Tieman reaction (B) Friedel Craft's acylation
(C) Wurtz reaction (D) Cannizzaro reaction
33. Which is the major product formed when acetone is heated with iodine and potassium hydroxide ?
[IIT Mains Online 2014]
(A) Iodoacetone (B) Acetic acid (C) Iodoform (D) Acetophenone
Cl O
H2SO4
2 + H – C – CCl 3 [IIT Mains Online 2014]
Cl Cl
(A) Cl C Cl (B) Cl C Cl
Cl CH2Cl
(C) Cl CH Cl (D) Cl CH Cl
CCl3 Cl
36. A compound A with molecular formula C10H13Cl gives a white precipitate on adding silver nitrate solution. A on
reacting with alcoholic KOH gives compound B as the main product. B on ozonolysis gives C and D. C gives
Cannizaro reaction but not aldol and D gives aldol but not Cannizaro reaction. A is :
[IIT Mains Online 2015]
CH3
C6H5–CH2–CH2–CH–CH3
(A) C6H5–CH2–C (B)
CH3 Cl
Cl
CH2–CH2–CH3
CH2–Cl
(C) C6H5–CH2–CH2–CH2–CH2–Cl (D)
OCOCH3
COOH
37. is used as [IIT Mains Online 2015]
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JEE ADVANCE
EXERCISE-I
1. Which one of the following is mixed ketone (Aliphatic & aromatic) :
O O O O
||
(A) CH 3 – C – CH 3 (B) CH3 – CH2 – C – CH3 (C) Ph – C – CH3 (D) CH3 C 6H4 C CH2Ph
O O O
|| || ||
(A) CH3 – C – H (B) CH3 – C – CH3 (C) CH3 – C – OH (D) CH3 – CH2 – OH
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EXERCISE-II
Single Choice Questions :
1. The reagent with which both acetaldehyde and acetone react easily is [IIT 1982]
(A) Tollen reagent (B) Schiff reagent (C) Grignard reagent (D) Fehling reagent
2. The Cannizzaro reaction is not given by
(A) trimethyl acetaldehyde (B) acetaldehyde [IIT 1983]
(C) benzaldehyde (D) formaldehyde
3. When acetaldehyde is heated with Fehling solution, it gives a precipitate of [IIT 1983]
(A) Cu (B) CuO (C) Cu2O (D) Cu + Cu2O + CuO
4. The formation of cyanohydrin from a ketone is an example of: [IIT 1990]
(A) Electrophilic addition (B) Nucleophilic addition
(C) Nucleophilic substitution (D) Electrophilic substitution
5. m-chlorobenzaldehyde on reaction with conc. KOH at room temperature gives: [IIT 1991]
(A) Potassium m-chlorobenzoate and m-hydroxybenzaldehyde
(B) m-hydroxybenzaldehyde and m-chlorobenzyl alcohol
(C) m-chlorobenzyl and m-hydroxybenzyl alcohol
(D) Potassium m-chlorobenzoate and m-chlorobenzyl alcohol
6. Hydrogenation of benzoyl chloride in the presence of Pd and BaSO4 gives: [IIT 1992]
(A) Benzyl alcohol (B) Benzaldehyde (C) Benzoic acid (D) Phenol
7. An organic compound C3H6O does not give a precipitate with 2,4-Dinitrophenyl hydrazine reagent and does
not react with metallic sodium. It could be: [IIT 1993]
(A) CH3CH2CHO (B) CH3COCH3 (C) CH2=CH–CH2OH (D)CH2=CH–O–CH3
8. Under Wolff Kishner reduction conditions, the conversions which may be brought about is? [IIT 1995]
(A) Benzaldehyde into Benzyl alcohol (B) Cyclohexanol into Cyclohexane
(C) Cyclohexanone into Cyclohexanol (D) Benzophenone into Diphenylmethane
9. In the reaction, P is [IIT 1995]
SeO
CO 2
P + Se + H2O
10. OH
In the Cannizzaro reaction given below, 2Ph–CHO Ph–CH2OH + PhCO 2 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 the carboxylic acid
(D) the deprotonation of Ph–CH2OH [IIT 1996]
11. Among the given compounds, the most susceptible to nucleophilic attack at the carbonyl group is
(A) MeCOCl (B) MeCHO (C) MeCOOMe (D) MeCOOCOMe [IIT 1996]
12. In a Cannizzaro reaction the intermediate which is the best hydride donor is: [IIT 1997]
H H
| |
C H
(A) 6 5 C O C H
(B) 6 5 C O (C) (D)
| |
OH O
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2
21. Ph – C C – CH3 A
Hg / H
[IIT 2003]
A is
O O
Ph Ph Ph Ph
O OH
(A) (B) (C) (D)
CH3 CH3 CH3 CH3
CH COONa
22. + X 3 [IIT 2005]
What is X?
(A) CH3COOH (B) BrCH2, COOH (C) (CH3CO)2O (D) CHO–COOH
23. How will you convert butane-2-one to propanoic acid? [IIT 2005]
(A) Tollen reagent (B) Fehling solution (C) NaOH / I2 / H+ (D) NaOH / NaI /H+
24. The smallest ketone and its next homologue are reacted with NH2OH to form oxime. [IIT 2006]
(A) Two different oximes are formed (B) Three different oximes are formed
(C) Two oximes are optically active (D) All oximes are optically active
25. Which of the following reactants on reaction with conc. NaOH followed by acidification gives the following
lactone as the only product? [IIT 2006]
26. Cyclohexene on ozonolysis followed by reaction with zinc dust and water gives compound E. Compound E
on further treatment with aqueous KOH yields compound F. Compound F is [IIT 2007]
27. Statement-1 : Glucose gives a reddish-brown precipitate with Fehling’s solution. [IIT 2007]
because
Statement-2 : Reaction of glucose with Fehling’s solution gives CuO and gluconic acid.
(A) Statement-1 is True, Statement-2 is True; Statement-2 is a correct explanation for Statement-1.
(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for Statement-1.
(C) Statement-1 is True, Statement-2 is False.
(D) Statement-1 is False, Statement-2 is True.
28. The number of aldol reaction (s) that occurs in the given transformation is : [IIT 2012]
OH OH
HO
OH
+ -
NH3I
(B) HO (Q) gives positive FeCl3 test
COOH
+ -
(C) HO NH3Cl (R) gives white precipitate with AgNO3
+ -
(D) O2N NH – NH3Br (S) reacts with aldehydes to form the corresponding
hydrazone derivative
NO2
Paragraph for Question No. 34 to 36 [IIT 2008]
A tertiary alcohol H upon acid catalysed dehydration gives a product I. Ozonolysis of I leads to compounds
J and K. Compound J upon reaction with KOH gives benzyl alcohol and a compound L, whereas K on
reaction with KOH gives only M.
O
H3C
Ph
M=
Ph H
O O
|| ||
(A) + PhMgBr (B) + PhCH2MgBr
Ph CH3 Ph CH3
O O Me
(C)
|| + PhCH2MgBr (D)
|| +
Ph H Ph H Ph MgBr
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40. The compound R is
O O O CH3 O
|| CH3 | ||
|| | ||
C H3C C C CH CH
H3C CH
C H C H H3C CH H H3C CH H
(A) H3C | (B) H3C | (C) | (D) |
H2C CH H2C CH
OH H3C OH OH H3C OH
CH3 O O CH3 CN CN
| || || | | |
CH C H3C C CH CH H3C CH
H3C CH H C H H3C CH OH C OH
(A) | (B) H3C | (C) | (D) H3C |
H2C H2C H2C H2C
CN CN OH OH
42. Amongst the following, the total number of compounds soluble in aqueous NaOH is [IIT 2010]
H3C CH3
N COOH OCH2CH3 OH
CH2OH
OH
NO2 CH2CH3 COOH
CH2CH3
N
H3C CH3
43. After completion of the reactions (I and II), the organic compound(s) in the reaction mixtures is(are)
O
Br2(1.0 mol)
Reaction I : H3C CH3 aqueous/NaOH [JEE ADVANCE : 2013]
(1.0 mol)
O O O O O
H3C CH2Br H3C CBr3 Br3C CBr3 BrH2C CH2Br H3C ONa CHBr3
P Q R S T U
(A) Reaction I : P and Reaction II : P
(B) Reaction I : U, acetone and Reaction II : Q, acetone
(C) Reaction I : T, U, acetone and Reaction II : P
(D) Reaction I : R, acetone and Reaction II : S, acetone
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46. Different possible thermal decomposition pathways for peroxyesters are shown below. Match each pathway
from List-I with an appropriate structure from List - II and select the correct answer using the code given
below the lists. [JEE Advance 2014]
P
R• + RO•
– CO2
O Q
|| R• + RO• R• + X• + carbonyl compound
R O
O
R – CO2
(Peroxyester)
R
RCO2• + RO• R• + X• + carbonyl compound
– CO2
S RCO2• RO• R• + RO•
– CO2
List - I List - II
(P) Pathway P 1.
(Q) Pathway Q 2.
(R) Pathway R 3.
(S) Pathway S 4.
Codes :
P Q R S
(A) 1 3 4 2
(B) 2 4 3 1
(C) 4 1 2 3
(D) 3 2 1 4
H3C
i. O3 NH3
R S
ii. Zn, H2O
H3C H3C N
N
(A) (B)
N N
(C) (D)
H3C H3C
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Paragraph (Q.53 to Q.54) [JEE ADVANCE 2016]
Treatment of compound O with KMnO4/H+ gave P, which on heating with ammonia gave Q. The compound
Q on treatment with Br2/NaOH produced R. On strong heating, Q gave S, which on further treatment with
ethyl 2-bromopropanoate in the presence of KOH followed by acidification, gave a compound T.
(O)
O O O
NH2
Br NHBr
(A) (B) (C) (D) NBr
Br NHBr
NH2
O O O
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ANSWER KEY
JEE MAINS
EXERCISE-I
1. B 2. C 3. D 4. B 5. D 6. D 7. B
8. C 9. D 10. C 11. B 12. C 13. C 14. B
15. C 16. B 17. D 18. C 19. D 20. A 21. B
22. B 23. B 24. D 25. C 26. B 27. A 28. D
29. B 30. C 31. A 32. B 33. A 34. D 35. A
36. B 37. A 38. B 39. B 40. C 41. B 42. C
43. D 44. A 45. C 46. D 47. C 48. C 49. B
50. D 51. C 52. D 53. C 54. D 55. D 56. C
57. B 58. A 59. D 60. B 61. C 62. C 63. D
64. B 65. B 66. B
EXERCISE-II
1. C 2. A 3. A 4. C 5. A 6. D 7. C
JEE ADVANCE
EXERCISE-I
1. C, D 2. B, C 3. A, B 4. A, B, C, D 5. A, B
6. B, D 7. A, B, C, D 8. B, C 9. A 10. A, B, C
11. A, D 12. A, B, C, D 13. A 14. D 15. C
16. A P, S ; B Q, S ; C Q, S ; D R, S
EXERCISE-II
1. C 2. B 3. C 4. B 5. D 6. B 7. D
8. D 9. A 10. B 11. A 12. D 13. B 14. A
15. B 16. A 17. C 18. A 19. C 20. A,B 21. A
22. C 23. C 24. B 25. C 26. A 27. C 28. C
29. A 30. A 31. ABD 32. A P, S ; B Q,R ; C Q, R, S ; D Q,R
33. A – R,S ; B – P,Q ; C – P,Q,R ; D – P,S (OR) A – R ; B – P,Q ; C – P,Q,R ; D – P
34. B 35. A 36. D 37. D 38. B 39. B
40. A 41. D 42. 4 [(ii), (iv), (vi), (viii)] 43. C 44. A 45. ABCD
46. A 47. A 48. A 49. BC or BCD 50. ABC 51. A
52. A 53. A 54. B
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