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Test: Reaction of Alcohols - II - NEET MCQ


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Test: Reaction of Alcohols - II - Question 1

Only One Option Correct Type

Direction (O. 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. 

Arrange the following alcohols in the increasing order of reactivity with HBr.
I. benzyl alcohol
II. p-methyl benzyl alcohol
III. p-nitrobenzyl alcohol
IV. p-chlorobenzyl alcohol

Detailed Solution for Test: Reaction of Alcohols - II - Question 1

Reactive intermediate carbocation is involved, hence greater the stability of carbocation, greater the reactivity of corresponding alcohols. Methyl group gives electron donating + I-effect, increases stability of carbocation, nitro group and chloro have both - I-effect, decreases stability of carbocation. Nitro group has stronger electron withdrawing power than chloro, nitro derivative is further less reactive than chloro derivative.

Test: Reaction of Alcohols - II - Question 2

 Which is the most appropriate reagent for the following oxidation reaction?

CH3 —CH = CH — CH2OH → CH3 —CH =CH — COOH 

Detailed Solution for Test: Reaction of Alcohols - II - Question 2

It is Jone's reagent which does not affect the olefinic bonds.

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Test: Reaction of Alcohols - II - Question 3

What is the major product of the following reaction ?

Detailed Solution for Test: Reaction of Alcohols - II - Question 3

Test: Reaction of Alcohols - II - Question 4

Which of the following is true statem ent regarding reaction of c/s and trans 2-hexene with CH3OH/H+ ?

Detailed Solution for Test: Reaction of Alcohols - II - Question 4

Both cis and trans 2-hexene form s the same carbocation, hence react at same rate.

Test: Reaction of Alcohols - II - Question 5

The major product formed in the following reaction is 

Detailed Solution for Test: Reaction of Alcohols - II - Question 5

Test: Reaction of Alcohols - II - Question 6

The relative rate of reaction of the following with H2SO4

Detailed Solution for Test: Reaction of Alcohols - II - Question 6

Reaction proceeds via carbocation intermediates. Hence, greater the stability of carbocation, greater the reactivity.

Test: Reaction of Alcohols - II - Question 7

The major product in the following reaction is

Detailed Solution for Test: Reaction of Alcohols - II - Question 7


Test: Reaction of Alcohols - II - Question 8

What is the major product of the following reaction?

Detailed Solution for Test: Reaction of Alcohols - II - Question 8

*Multiple options can be correct
Test: Reaction of Alcohols - II - Question 9

One or More than One Options Correct Type

Direction (0 . 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. 

What is/are the expected product(s) in the following reaction?

Detailed Solution for Test: Reaction of Alcohols - II - Question 9

Reaction proceeds via carbocation intermediates.


*Multiple options can be correct
Test: Reaction of Alcohols - II - Question 10

What is/are the possible dehydration product(s) in the following reaction?

Detailed Solution for Test: Reaction of Alcohols - II - Question 10


*Multiple options can be correct
Test: Reaction of Alcohols - II - Question 11

What is/are the possible dehydration product(s) in the following reaction?

Detailed Solution for Test: Reaction of Alcohols - II - Question 11





 

*Multiple options can be correct
Test: Reaction of Alcohols - II - Question 12

In which of the following reaction(s), reactant and product(s) are correctly matched ? 

Detailed Solution for Test: Reaction of Alcohols - II - Question 12




(d) No SN2 reaction on C6H5Br.

*Multiple options can be correct
Test: Reaction of Alcohols - II - Question 13

In the following dehydration reaction, expected product(s) is/are

Detailed Solution for Test: Reaction of Alcohols - II - Question 13


*Multiple options can be correct
Test: Reaction of Alcohols - II - Question 14

Upon treatment with bromine water, allyl bromide gives chiefly primary alcohol BrCH2CHBrCH2OH. What are the expected primary alcohols in the following reaction ?

Detailed Solution for Test: Reaction of Alcohols - II - Question 14



Nucleophilic attack of H2O occur at α-C of cyclic bromonium ion where positive charge is more easily accommodated.

Test: Reaction of Alcohols - II - Question 15

Comprehension Type

Direction (Q. Nos. 15-19) This section contains 2 paragraphs, each describing theory, experiments, data, etc. Five 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

An unknown organic compound A is determined to have molecular formula C6H12O and passing it through chiral column does not separate it into enantiomers. A does not react with Br2 nor with cold, dilute alkaline KMnO4. Heating A with concentrated H2SO4 gives product B (C6H10) which can be separated into enantiomers. Ozonolysis of a single enantiomer of B produces C, an optically active keto-aldehyde of formula C6H10O2 which gives positive iodoform test.

Q. 

Structure of B that satisfy the above criteria is

Detailed Solution for Test: Reaction of Alcohols - II - Question 15

Test: Reaction of Alcohols - II - Question 16

Passage I

An unknown organic compound A is determined to have molecular formula C6H12O and passing it through chiral column does not separate it into enantiomers. A does not react with Br2 nor with cold, dilute alkaline KMnO4. Heating A with concentrated H2SO4 gives product B (C6H10) which can be separated into enantiomers. Ozonolysis of a single enantiomer of B produces C, an optically active keto-aldehyde of formula C6H10O2 which gives positive iodoform test.

Q. 

The correct statement regarding C is

Detailed Solution for Test: Reaction of Alcohols - II - Question 16


Test: Reaction of Alcohols - II - Question 17

Passage I

An unknown organic compound A is determined to have molecular formula C6H12O and passing it through chiral column does not separate it into enantiomers. A does not react with Br2 nor with cold, dilute alkaline KMnO4. Heating A with concentrated H2SO4 gives product B (C6H10) which can be separated into enantiomers. Ozonolysis of a single enantiomer of B produces C, an optically active keto-aldehyde of formula C6H10O2 which gives positive iodoform test.

Q. 

The correct statement regarding the outcome of the following reaction is

Detailed Solution for Test: Reaction of Alcohols - II - Question 17



Hydroboration oxidation brings about syn, anti-Markownikoff’s addition of water at 

Test: Reaction of Alcohols - II - Question 18

Passage II

An organic compound P (C10H18O)w hen treated with Br2(l) gives Q (C10H18OBr4). P on vigorous oxidation gives the following compounds 

Q. 

What is the structural formula of P?

Detailed Solution for Test: Reaction of Alcohols - II - Question 18




X also gives the same bromide as it also involves the same carbocation in the final step.

Test: Reaction of Alcohols - II - Question 19

Passage II

An organic compound P (C10H18O)w hen treated with Br2(l) gives Q (C10H18OBr4). P on vigorous oxidation gives the following compounds 

Q. 

P on treatment with dilute acid undergo isomerisation to a more stable isomer R. What is the most likely structure of R ?

Detailed Solution for Test: Reaction of Alcohols - II - Question 19

*Answer can only contain numeric values
Test: Reaction of Alcohols - II - Question 20

One Integer Value Correct Type

Direction (Q. Nos. 20-23) This section contains 4 questions. When worked out will result in an integer from 0 to 9 (both inclusive).

In the reaction given below isotopic exchange occur

Q.

What is the maximum gain in molecular mass observed?


Detailed Solution for Test: Reaction of Alcohols - II - Question 20


via protonation, all —OH will beco me , giving an increase in 3 units of mass per —OH group

*Answer can only contain numeric values
Test: Reaction of Alcohols - II - Question 21

Consider the following dehydration reaction,

Q. 

If a pure enantiomer of alcohol is taken, then how many different alkenes are formed?


Detailed Solution for Test: Reaction of Alcohols - II - Question 21





Since, only a pure enantiomer A is taken, only c/s and frans-isomers of (I) would be produced. (II) will also be formed in cis-trans pair. (Ill) will also be formed as a pair of cis-trans isomer and (IV) will be a single isomer.

*Answer can only contain numeric values
Test: Reaction of Alcohols - II - Question 22

 In the following reaction how many different diols, are formed?


Detailed Solution for Test: Reaction of Alcohols - II - Question 22

*Answer can only contain numeric values
Test: Reaction of Alcohols - II - Question 23

If all carbonyls isomers of molecular mass = 86 u are separately treated with CH3MgBr followed by acid hydrolysis, how many of them will give racemic mixture ?


Detailed Solution for Test: Reaction of Alcohols - II - Question 23

The carbonyl C5H10O (CnH2nO = 86) has following isomers.


Compounds (III), (IV), (VI) and (VII) gives racemic mixture with CH3MgBr. (I) and (II) gives achiral alcohols with CH3MgBr. (V) is enantiomeric, a pure enantiomer it gives pair of diastereomers with CH3MgBr.

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