Revisal Problems (Past 13 Year) JEE Advanced (Aliphatic Aldehydes And Ketones)


30 Questions MCQ Test Chemistry for JEE Advanced | Revisal Problems (Past 13 Year) JEE Advanced (Aliphatic Aldehydes And Ketones)


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QUESTION: 1

Only One Option Correct Type

Direction (Q. Nos. 1-8) This section contains 8 multiple choice questions. Each question has four choices (a), (b), (c) and (d), out of which ONLY ONE is correct.

Q. 

The best reagent that can bring about the following conversion is

Solution:

Clemmensen reduction is most suitable here. If Wolff-Kishner reduction is used, OH- may simultaneously bring about SN2 and E2 reaction with halide group.

QUESTION: 2

Which carbon-carbon bond could not be formed by an aldol condensation reaction?

Solution:

α, β-carbon-carbon bond is form ed in aldol condensation reaction.

QUESTION: 3

Arrange the following in the increasing order of hydrate content when dissolved in water.




Solution:

Hydrate formation involves nucleophilic addition at carbonyl carbon in the slow rate determining step. Therefore, electron withdrawing group increases reactivity while electron donating group decreases reactivity of carbonyls.

QUESTION: 4

What is the major product in the following sequence of reaction?

  

Solution:

QUESTION: 5

An organic compound A (C6H12O) neither decolourise bromine water nor changes the colour of acidic dichromate solution. A on heaing with H2SO4 produces an alkene which on oxidative ozonolysis gives B (C6H10O3) which gives a yellow precipitate with NaOH/I2. The most probable structure of A is 

Solution:

QUESTION: 6

Which of the following is not true regarding the reaction given below.

Solution:

Product is in conjugated system, more stable than non-conjugated reactant.

QUESTION: 7

Which of the following compounds exchanges the largest number of hydrogens from deuterium when treated with KOD in D2O ?

Solution:

It has eight α-H which can undergo exchange with deuterium.

QUESTION: 8

Treatment of cyclohexanone with an excess of produced 18O labelled cyclohexanone. Which of the following is a likely intermediate in this isotope exchange? (the isotope is not named)

Solution:

*Multiple options can be correct
QUESTION: 9

One or More than One Options Correct Type

Direction (Q. Nos. 9-14) This section contains 6 multiple choice questions. Each question has four choices (a), (b), (c) and (d), out of which ONE or MORE THAN ONE are correct.

Q. 

Which is/are the expected products in the following reaction ?

Solution:


The oxime above undergoes Beckmann rearrangement on treatment with concentrated H2SO4. Rearrangement by route (1) gives (a) while rearrangement by route (2) gives (d).

*Multiple options can be correct
QUESTION: 10

Treatment of A (C5H12O) with concentrated sulphuric acid results in the formation of three alkenes in differing yields. Also, A forms a yellow precipitate on treatment with NaOH/I2. A turns colour of acidified dichromate solution to blue green, forming a new organic compound B which also forms yellow precipitate on treatment with NaOH/I2. The most likely name of A is 

Solution:

A is a 2° alcohol with CH3H (OH)—group.

*Multiple options can be correct
QUESTION: 11

The carbonyl compound(s) that will undergo racemisation on treatment with aqueous KOH is(are)

Solution:



*Multiple options can be correct
QUESTION: 12

Which of the following reagants can bring about the transformation shown below ?

Solution:

All these reagents (a,b,c) can be used for selective oxidation of alcohol without affecting olefinic bond. However, KMn04 in acidic medium will attack olefinic bond too besides oxidising alcoholic group.

*Multiple options can be correct
QUESTION: 13

Which of the following reactions has/have equilibrium constant (Kc) greater than one?

Solution:

In both option (b) and option (c) cases, the product enol is more stable than reactant keto, hence Kc is greater than 1.

*Multiple options can be correct
QUESTION: 14

Which of the following, on treatment with NaHSO3(aq), will produce mixture of salts which can be separated by fractional crystallisation?

Solution:

All these will produce diastereomeric salts with NaHSO3, hence can be separated by fractional crystallisation.

QUESTION: 15

Statement Type

Direction(Q. Nos. 15 and 16) This section is based on Statement I and Statement II. Select the correct answer from the codes given below.

Q. 

Statement I : When benzaldehyde (C6H5CHO) is treated with concentrated NaOD solution in D2O , Cannizaro reaction occur but no C—D (bonds with deuterium) is formed.

Statement II : Cannizaro reaction involves hydride transfer mechanism.

Solution:

Cannizaro reaction involves hydride (H-) transfer from one aldehyde to another aldehyde m olecule, hence, C—D bond cannot be formed if D2O/NaOD is used.

QUESTION: 16

Statement I : Consider the reaction given below,

Statement II : Aldehydes and ketones react with semicarbazide to form semicarbazone.

Solution:

Nucleophilic attack occur from aminic nitrogen not from amidic nitrogen.

QUESTION: 17

Comprehension Type

Direction (Q. Nos. 17-22) This section contains 2 paragraphs, each describing theory, experiments, data, etc. Six questions related to the paragraphs have been given. Each question has only one correct answer among the four given options (a), (b), (c) and (d).  

Passage I

Q. 

Which of the follwing can not be B ?

Solution:

In aldol condensation reaction follow ed by dehydration of aldol gives α, β-unsaturated carbonyl compound not the β, γ-unsaturaied carbonyl as major product.

QUESTION: 18

Passage I

Q. 

Which of the following is most likely structure of C ?

Solution:

In first step, the more reactive aldehyde group is acetylated and then ketonic group is reduced with LiAIH4. In the final step, hemiacetal formation occur at aldehyde group.

QUESTION: 19

Passage I

Q. 

Which of the following most likely structure of D ?

Solution:

Dicarbonyl on heating with hydrazine forms cyclic hydrazone.

QUESTION: 20

Passage II

A chiral organic compound A (C9H12O2) does not give positive Tollen's test or iodoform test. However, A on treatment with 1.0 equivalent of CH3MgBr followed by acid hydrolysis gives B (C10H16O2) which gives positive iodoform test. B on refluxing with aqueous Na2CO3 solution gives the following compound as major product.

Q. 

 What is the most probable structure of A ?

Solution:

By carrying out the retro-aldol synthesis, the structure of B can be known as

QUESTION: 21

 

Q. 

B on treatment with hydrazine (N2H4) gives a cyclic hydrazone. What is the structure of hydrazone?

Solution:

Dicarbonyl B shown above on heating w ith N2H4 gives a cyclic hydrazone.

QUESTION: 22

Passage II

A chiral organic compound A (C9H12O2) does not give positive Tollen's test or iodoform test. However, A on treatment with 1.0 equivalent of CH3MgBr followed by acid hydrolysis gives B (C10H16O2) which gives positive iodoform test. B on refluxing with aqueous Na2CO3 solution gives the following compound as major product.

Q. 

If compound B is treated with excess of CH3MgBr followed by acid hydrolysis, how many different alcohols would be obtained?

Solution:

QUESTION: 23

Matching List Type

Direction (Q. Nos. 23-25) Choices for the correct combination of elements from Column I and Column II are given as options (a), (b), (c) and (d), out of which one is correct.

Q. 

Match the Column I with Column II and mark the correct option from the codes given below.

Solution:





QUESTION: 24

Match the Column I with Column II and mark the correct option from the codes given below.

Solution:






QUESTION: 25

Match the following reactions of Column I with products from the Column II.

Solution:





On hydride transfer with CH2OI gives DCOOH and DCH2OH while (II) on hydride transfer with CD2O gives D2CHOH.


*Answer can only contain numeric values
QUESTION: 26

One Integer Value Correct Type

Direction (Q. Nos. 26-30) This section contains 5 questions. When worked out will result in an integer from 0 to 9 (both inclusive).

Q. 

If propanal (CH3CH2CHO) is treated with DCI in D2O, keto-enol equilibria are established. At equilibrium, how many different enols would be existing?


Solution:

*Answer can only contain numeric values
QUESTION: 27

Butanone + Dil. NaOH → Aldol (C8H16O2

How many different aldol would be formed?


Solution:

*Answer can only contain numeric values
QUESTION: 28

How many different alcohols would be formed in the above reaction?


Solution:


After H- transfer, (i) gives CH3OH and CD2HOH and while (II) gives CD2OH and CDH2OH.

*Answer can only contain numeric values
QUESTION: 29

In the reaction given below, how many different oximes would be formed?


Solution:


Four stereoisomers exist for I, cis-cis, trans- trans and cis-trans with OH syn to cis and OH anti to cis.

*Answer can only contain numeric values
QUESTION: 30

Consider the following reactions,

Q. 

How many different amides are formed in the above reactions?


Solution:

Both products have one chiral carbon each, hence two pairs of enantiomers are formed.