ONLINE NEET OBJECTIVE EXAMINATION

CHEMISTRY
10 - 09 - 2020

21K/TP/NEET/ ALDEHYDES AND KETONES BATCH : All residential

1. The major product(s) obtained in the following reaction is/are

(i) KOBu
 
(ii)O3 / Me2S


1) 2)

3) 4)

2. In the following reaction,


HCl
Carbonyl compound + MeOH   acetal
Rate of the reaction is the highest for :
1) Acetone as substrate and methanol in excess
2) Propanal as substrate and methanol in stoichiometric amount
3) Acetone as substrate and methanol in stoichiometric amount
4) Propanal as substrate and methanol in excess
3. The major product obtained in the following reaction is


NaOH
D


1) 2) 3) 4)

4. The major product of the following reaction is

(1)t  BuOK

(2)Conc.H 2SO4 / 


1) 2) 3) 4)
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5. An organic compound neither reacts with neutral ferric chloride solution nor with Fehling solution. It however,
reacts with Grignard reagent and gives positive iodoform test. The compound is

1) 2) 3) 4)

6. In the following reactions, products A and B are


Dil.NaOH
 A

 A     B

H O
3


1) A = ;B=

2) A = ;B=

3) A = ;B=

4) A = ;B=

7. The major product obtained in the following reaction is

LiAlH 4
 
excess


1) 2) 3) 4)
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8. The correct match between item ‘I’ and item ‘II’ is

Item ‘I’ (Compound) Item ‘II’ (Reagent)
A) Lysine P) 1-naphthol
B) Furfural Q) Ninhydrin
C) Benzyl alcohol R) KMnO4
D) Styrene S) Ceric ammonium nitrate
Codes
A B C D
1) Q R S P
2) R P Q S
3) Q P S R
4) Q P R S
9. The major product ‘X’ formed in the following reaction is


NaBH4
MeOH
X

1) 2)

3) 4)

10. The correct sequence of reagents for the following conversion will be


1)  Ag  NH3 2  OH  , H  / CH3OH, CH 3 MgBr


2) CH 3 MgBr, H  / CH 3OH,  Ag  NH 3  2  OH 


3) CH 3MgBr,  Ag  NH3 2  OH  , H  / CH3OH


4)  Ag  NH3 2  OH  , CH 3 MgBr, H  / CH 3OH
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11. The major product of the following reaction sequence is


(i)HCHO (excess) / NaOH,Heat
(ii)HCHO / H   catalytic amount 


1) 2)

3) 4)

12. Which compound would give 5-keto-2-methyl hexanal upon ozonolysis ?

CH3 CH3 CH3

CH3
CH3 H3C
1) 2) 3) 4)
CH3 H3C

13. The major product in the following reaction is

0

(i)CH3MgBr,dryether,0 C
(ii) Aqueous acid


1) 2)

3) 4)

14. The most suitable reagent for the conversion of R  CH 2  OH  R  CHO is

1) KMnO4 2) K2Cr2O7
3) CrO3 4) PCC (pyridinium chlorochromate)
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15. The major product H in the given reaction sequence is

CN G 
95% H 2SO 4
H
CH 3  CH 2  CO  CH 3

1) 2)

3) 4)

16. The number of aldol reaction(s) that occurs in the given transformation is

CH3CHO + 4HCHO 

Conc.aq.NaOH


1) 1 2) 2 3) 3 4) 4
17. 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

1) 2) 3) 4)

18. The smallest ketone and its next homologue are reacted with NH2OH to form oxime
1) two different oximes are formed 2) three different oximes are formed
3) two oximes are optically active 4) all oximes are optically active
19. Butan-2-one can be converted to propanoic acid by which of the following ?
1) NaOH, NaI/H+ 2) Fehling’s solution 3) NaOH, I2/H+ 4) Tollen’s reagent

20. + (X) 

CH 3COONa

What is X ?
1) CH3COOH 3) BrCH2COOH 3) (CH3CO)2O 4) HOC  COOH
21. The order of reactivity of phenyl magnesium bromide with the following compounds is

1) (II) > (III) > (I) 2) (I) > (III) > (II) 3) (II) > (I) > (III) 4) All of these
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22. A mixture of benzaldehyde and formaldehyde on heating with aqueous NaOH solution gives
1) benzyl alcohol and sodium formate 2) sodium benzoate and methyl alcohol
3) sodium benzoate and sodium formate 4) benzyl alcohol and methyl alcohol
23. The appropriate reagent for the following transformation :

1) Zn(Hg), HCl 2) NH 2NH2, OH- 3) H2/Ni 4) NaBH4

24. Which of the following has the most acidic hydrogen ?
1) 3-hexanone 2) 2,4-hexanedione 3) 2,5-hexanedione 4) 2,3-hexanedione
25. The enol form of acetone, after treatment with D2O, gives

1) 2) 3) 4)

26. Which of the following will react with water ?

1) CHCl3 2) Cl3CCHO 3) CCl4 4) ClCH2CH2Cl
27. Which of the following compounds is oxidised to prepare methyl ethyl ketone ?
1) 2-propanol 2) 1-butanol 3) 2-butanol 4) t-butyl alcohol
28. The compound that will not give iodoform on treatment with alkali and iodine is
1) acetone 2) ethanol 3) diethyl ketone 4) isopropyl alcohol
29. The Cannizzaro’s reaction is not given by
1) trimethyl acetaldehyde 2) acetaldehyde
3) benzaldehyde 4) formaldehyde
30. When acetaldehyde is treated with Fehling’s solution, it gives a precipitate of
1) Cu 2) CuO 3) Cu2O 4) Cu + Cu2O + CuO
31. A compound that gives a positive iodoform test is
1) 1-pentanol 2) 3-pentanone 3) 2-pentanone 4) pentanal
32. The reagent with which both acetaldehyde and acetone react easily is
1) Tollen’s reagent 2) Schiff’s reagent 3) Grignard’s reagent 4) Fehling’s reagent
33. Reagent(s) which can be used to bring about the following transformation is (are)

1) LiAlH4 in (C2H5)2O 2) BH3 in THF

3) NaBH4 in C2H5OH 4) Raney Ni/H2 in THF
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34. The major product of the following reaction is


(i) KOH, H 2 O
(ii) H  , Heat


1) 2)

3) 4)

35. After completion of the reaction (I and II), the organic compound(s) in the reaction mixtures is/are

2 
Br 1.0 mol
Reaction I 
Aqueous / NaOH


2 
Br 1.0mol
Reaction II 
CH 3COOH


1) reaction I : P and reaction II : P

2) reaction I : U, acetone and reaction II : Q, acetone
3) reaction I : T, U, acetone and reaction II : P
4) reaction I : R, acetone and reaction II : S, acetone
36. In Cannizzaro reaction given below
 
Ph  CHO 
OH
Ph  CH 2  OH  PhCO O
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 carboxylic acid.
4) the deprotonation of Ph  COOH
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37. Which of the following will be most readily dehydrated in acidic conditions ?

1) 2)

3) 4)

38. The appropriate reagent for the transformation is

1) Zn (Hg)/HCl 2) NH 2  NH 2 / OH 

3) Both 1 and 2 4) None of these

39. Benzaldehyde on reaction with CH 2  CH  CHPPh 3 forms

1) 2)

3) 4)

40.

Which one of the following reagents is used in the above reaction ?

1) aq. NaOH + CH3Cl 2) aq. NaOH + CH2Cl2
3) alc. NaOH + CHCl3 4) alc. NaOH + CCl4
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41. Predict the product of the following reaction :

Me
H2SO4
Me
OH OH

Me Me

1) Me 2) Me
O
O

Me
Me Me

3) 4)
O O
Me
42. 1,3 - dithiane is obtained from which of the following reactions
1) 1,3 - propanedithiol + H2CO 2) 1,3 - propanedithiol + CO
3) 1,3 - propanedithiol + CH3CHO 4) 1,3 - propanedithiol + CO2

O
1
2
O
43. Ninhydrin exists as hydrate. Which C = O is hydrated ?
3 O

1) 1 2) 2 3) 3 4) All
44. Chloral hydrate (Cl3CCH(OH)2) is a hypnotic drug. It was used to force sailors to continue service on
ships. Which among the given statements is true ?
1) Its hydrate form is more stable than aldehyde form
2) Its aldehyde form is more stable than hydrate form
3) Both are equally stable
4) All are false
OH
45. N H2SO4
A

What is A

O
1) N SO3H 2) NH

O O

3) 4)
NH N SO3H
 ONLINE NEET OBJECTIVE EXAMINATION
CHEMISTRY
10 - 09 - 2020

21K/TP/NEET/ ALDEHYDES AND KETONES BATCH : All residential

1. 1

In step - 1 dehydrohalogenation reaction takes place. Here, hydrogen is eliminated from  -

carbon and the halogen is lost from  - carbon atom. As a result diene is formed.

Cyclohex- 1, 3 - diene on ozonolysis gives butane-1, 4- dial and ethane 1, 2 - dial

2. 4 Key Idea Aldehydes are more reactive than ketones in nucleophilic addition reaction

For the reaction,

Rate of reaction is the highest for propanal as substrate and methanol in excess. Propanal is an
aldehyde and more reactive than ketones. When MeOH is taken in excess then reaction moves
in the forward direction that results in the formation of acetal. Reaction involved is as follows:
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3. 3 It is an intramolecular aldol condensation reaction

4. 4
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5. 4 According to the given conditions, compound (d) neither reacts with neutral ferric chloride solu-
tion nor with Fehling solution. It however reacts with grignard reagent and gives positive iodo-
form test.
As the compound does not contain any phenolic –OH group. Hence, it gives negative neutral
FeCl3 test.

Compound gives reaction with RMgX as it contains

Compound with CH3CH – group undergoes iodoform test in presence of NaOH and I2.

OH

6. 2 The reactant in presence of dil. NaOH undergoes intramolecular aldol condensation reaction.
As a result of this,  - hydroxyketone (A) is obtained which on hydrolysis followed by heating
produces  .  - unsaturated ketone (B)
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7. 2 LiA IH 4 acts as a nucleophilic reducing agent that can reduce

8. 3

1)

2)

3)

4)

9. 2 NaBH4 is a selective reducing agent. It reduces carbonyl group into an alcohol but cannot
reduce an isolated C=C and an ester group too
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10. 1

Before final product is formed, intermediate is

11. 1
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12. 2 1)

2)

3)

4)
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13. 4 This problem indudes concept of nucleophilic addition reaction to carbonyl compound (ketone
here) and intramolecular nucleophilic substitution reaction.
Complete reaction sequence is as shown below:

14. 4

Pyridinium chlorochromate is the mild oxidising agent which causes conversion of alcohol to
aldehyde stage . While others causes conversion of alcohol to acid
15. 1 The first step is cyanohydrin reaction

In the second step the –CN of intermediate (I) is first hydrolysed and then dehydrated on heating
in the presence of conc. H2SO4.
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16. 3 The given reaction is an example of repeated aldol condensation followed by Cannizzaro reac-
tion.

In the last step, formaldehyde is oxidised and the other aldehyde is reduced giving the desired
products.
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17. 1

18. 2 Three different oximes are formed out of which two are optically active i.e. exists as a pair of
enantiomers while other is optically inactive.

19. 3

20. 3 and it is an example of Perkin’s reaction.

21. 3 The reactivity of carbonyl compound towards nucleophilic addition of Grignard’s reagent de-
pends on extent of steric hindrance at  - carbon. Greater the steric hindrance smaller the
reactivity. Hence, reactivity order is

22. 1

This is an example of cross Cannizzaro reaction in which formaldehyde is always oxidised.

23. 2

24. 2
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25. 2

26. 2

27. 3

28. 3

Above three compounds has the desired group for iodoform test. Diethyl ketone does not has
the required group for iodoform test.
29. 2 Aldehydes lacking presence of  - H undergo Cannizzaro reaction. When treated with aqueous
base CH3CHO does not undergo Cannizzaro reaction because it has  - H and in the presence
of aqueous base it undergoes aldol condensation.

30. 3

31. 3

32. 3 Grignard’s reagent reacts with both aldehydes and ketones while other three reagents reacts only
with aldehydes, not with ketones.
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33. 3

34. 1

35. 3

When CH3COCH and Br2 are in equimolar quantity, all the Br2 (limiting reactant) is converted
into desired products and 2/3 mole of CH3COCH3 remains unreacted, being in excess. When
acetone reacts with Br2 in acidic medium, there is monobromination of acetone.
Reactions II

CH3COCH3 and Br2 react in 1 :1 mole ratio and (P) is formed. In reaction I, (U) and (T)
are formed and acetone (reactant) remains unreacted. In reaction II, (P) is formed.
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36. 2 The transfer of hydride ion to the carbonyl group is the slowest or the rate determining step.

37. 1 Aldols, i.e,  -hydroxyaldehydes or  -hydroxyketones readily undergo dehydration to form ,  -

unsaturated aldehydes or ketones.

38. 2 Both Zn(Hg)/HCl and NH 2  NH 2 / OH  can reduce COCH3 group to CH 2  CH 3 but HCl will
also bring about replacement of OH group by Cl. Therefore, the most appropriate reagent is
NH 2  NH 2 / OH 
39. 4 Witting reaction

40. 3
41. 2 Pinacol-pinacolone rearrangement

Me Me Me
Me H+
Me Me
OH OH2 OH O

O
42. 1
HSCH2CH2CH2SH C
S S
H H H H
1,3-propanedithiol 1,3-dithiane
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O O
  OH
43. 2  

O H2O
OH
  
O O

Non hydrated
ninhydrin

  on either side of central C O make it C more electrophilic.

44. 1 Cl Cl OH

  
Cl C C O Cl C C OH

Cl H Cl H

(aldehyde form) (hydrate form)

Adjacent positive. More stable form
charges repel each other,
destabilising the system

45. 2 Beckmann rearrangement

O
OH
H2SO4
N NH

Cyclic amide