Revisal Problems (Past 13 Year) JEE Advanced (Alcohols Phenols And Ethers)


30 Questions MCQ Test Chemistry for JEE Advanced | Revisal Problems (Past 13 Year) JEE Advanced (Alcohols Phenols And Ethers)


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QUESTION: 1

Only One Option Correct Type

Direction (Q. Nos. 1-12) This section contains 12 multiple choice questions. Each question has four choices (a), (b), (c) and (d), out of which ONLY ONE is correct.

Consider the following reaction,

Q.

The correct statement regarding X is

Solution:

The major product is a tertiary alcohol, gives immediate turbidity with Lucas reagent.

QUESTION: 2

Reaction of (+) - 3 - methylcyclopentene with (i) Cl2, H2O and (ii) NaH will provide

Solution:


The two anti halohydrins above are diastereomers.

QUESTION: 3

From which alcohol and which alkyl halide could A be best prepared through Williamson ether synthesis?

Solution:

A primary alkyl halide and alkoxide would give the indicated product by SN2 reaction.

QUESTION: 4

A synthesis of 2,5 - dimethyl- 2 -hexanol from 2 - methylpropene requires the for mation of two four carbon intermediates, X and Y. These intermediates combine to give the desired product after the usual hydrolysis work-up. Select the appropriate methods of preparing X and Y from 2-methylpropene.

Solution:


Reaction of X and Y gives the desired product.

QUESTION: 5

What is the major product of the following reaction?

Solution:

It is a Pinacol-pinacolone rearrangement.

QUESTION: 6

A chiral C5H10O alcohol is reduced by catalytic hydrogenation to an achiral C5H12O alcohol. The original alcohol is oxidised by activated MnO2 to an achiral carbonyl compound (C5H8O). Which of the following might be the chiral alcohol?

Solution:


Also, allyl alcohol is oxidised by MnO2 to corresponding carbonyls.

QUESTION: 7

The Lucas test is used to distinguish small (7 or fewer carbons) 1°, 2° and 3° alcohols. The alcohol to be tested is added to a solution of anhydrous ZnCI2 in conc. HCI at room temperature. Which of the following statements is not correct ?

Solution:

White turbidity of alkyl halide is formed rather than gaseous alkene is formed.

QUESTION: 8

If the following 13C labelled compound undergo the following reaction, which product would be obtained ?

Solution:

QUESTION: 9

Which sets of reagents shown below would accomplish the fo llow ing transform ation?

Solution:

QUESTION: 10

A C5H12O compound is optically active, and is oxidised by PCC in CH2Cl2 to an optically active C5H10O product, which is racemised in acid or base. Which of the following best fits these facts ?

Solution:

QUESTION: 11

What is the major product of the reaction?

Solution:

QUESTION: 12

When treated with acid, the strained ether (I) is protonated on oxygen, and ring opens to give a resonance stabilised carbocation. Which diene listed below when treated with acid will give the same carbocation ?

Solution:

*Multiple options can be correct
QUESTION: 13

One or More than One Options Correct Type

Direction (Q. Nos. 13-18) 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. 

The reaction producing 2-ethyl-2-methyl oxirane is/are

Solution:




*Multiple options can be correct
QUESTION: 14

Compounds which on reduction can produce alcohols is/are

Solution:

All of these on reduction produces alcohols while amide gives amines on reduction.

*Multiple options can be correct
QUESTION: 15

Lucas test is used for distinguishing primary, secondary.and tertiary alcohols as:

Q. 

The correct statement regarding the above test is/are

Solution:

The first step is protonation of alcohol base. Weaker acid (greater pKa) is more substituted (higher degree) alcohols, hence reacts faster in Lucas test. Tertiary alcohols are not oxidised by dichromate but reacts very rapidly with Lucas reagent. Alcohols reacting faster with Na are stronger acid hence, less substituted, reacts slowly with Lucas reagent.

*Multiple options can be correct
QUESTION: 16

3-methyl-3-hexano! can be prepared by the reaction of

Solution:



*Multiple options can be correct
QUESTION: 17

The correct statement regarding the product(s) of the following reaction is/are

Solution:

Reduction wih LiAIH4 gives a pair of diastereorners.

*Multiple options can be correct
QUESTION: 18

Which of the following Grignard synthesis would fail to produce the desired alcohols?

Solution:

Option (a) has an acidic hydrogen will undergo neutralisation with CH3MgBr. Option (b) has a leaving group will undergo SN2 reaction with CH3MgBr. In option (c) the ether group may be hydrolysed in the final step.

QUESTION: 19

Comprehension Type Direction

(Q. Nos. 19-24) 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

A and B are two structural isomers with their molecular formula C7H14O and both gives-off effervescence on heating with Na-metal. However, neither A nor B decolourise brown colour of Br2-H2O. Treating either A or B with hot conc, sulphuric acid solution results in the form ation of the same compound C (C7H12). C on treatment with O3 followed by Zn-H2O gives D (C7H12O2). D gives E (C7H16O2) on treatm ent with NaBH4. E has only one methyl group and forms yellow ppt with I2/KOH. Also, A gives delayed turbidity on treatment with conc. HCI/ZnCI2 while B gives immediate turbidity on similar treatment.

Q. 

Which of the following statement regarding A and B is correct?

Solution:

Both A and B are alcohols with one degree of unsaturation but none of them decolourise Br2 - H2O solution,hence they are cyclic.

E has only one methyl group and gives iodoform test hence, E may be : 


A has a chiral carbon but B does not.

QUESTION: 20

Passage I

A and B are two structural isomers with their molecular formula C7H14O and both gives-off effervescence on heating with Na-metal. However, neither A nor B decolourise brown colour of Br2-H2O. Treating either A or B with hot conc, sulphuric acid solution results in the form ation of the same compound C (C7H12). C on treatment with O3 followed by Zn-H2O gives D (C7H12O2). D gives E (C7H16O2) on treatm ent with NaBH4. E has only one methyl group and forms yellow ppt with I2/KOH. Also, A gives delayed turbidity on treatment with conc. HCI/ZnCI2 while B gives immediate turbidity on similar treatment.

Q. 

Which of the following statement regarding A and B is incorrect?

Solution:

Both A and B are alcohols with one degree of unsaturation but none of them decolourise Br2 - H2O solution,hence they are cyclic.

E has only one methyl group and gives iodoform test hence, E may be : 


A has a chiral carbon but B does not.
B is a tertiary alcohol, does not react with SOCI2.

QUESTION: 21

Passage I

A and B are two structural isomers with their molecular formula C7H14O and both gives-off effervescence on heating with Na-metal. However, neither A nor B decolourise brown colour of Br2-H2O. Treating either A or B with hot conc, sulphuric acid solution results in the form ation of the same compound C (C7H12). C on treatment with O3 followed by Zn-H2O gives D (C7H12O2). D gives E (C7H16O2) on treatm ent with NaBH4. E has only one methyl group and forms yellow ppt with I2/KOH. Also, A gives delayed turbidity on treatment with conc. HCI/ZnCI2 while B gives immediate turbidity on similar treatment.

Q. 

Which of the following statement regarding acid catalysed isomerisation of A and B is true?

Solution:

Both A and B are alcohols with one degree of unsaturation but none of them decolourise Br2 - H2O solution,hence they are cyclic.

E has only one methyl group and gives iodoform test hence, E may be : 


A has a chiral carbon but B does not.

QUESTION: 22

Passage II

An organic compound A(C9H10O) is chiral and does not evolve any gas on treatment with Na-metal but on hydrolysis with dil. H2SO4 gives B (C9H12O2) which on further treatment with alkaline solution of iodine does not give an yellow precipitate. Also A on treatment with excess of conc. HBr gives C (C9H11OBr) as the major product. C on further treatment with C2H5ONa/C2H5OH followed by acidification of product gives D (an isomer of A). D on ozonolysis followed by work-up with dimethyl sulphide gives E (C8H8O2) as one of the product.

Q. 

The most likely structure of starting compound A is

Solution:




The compound A shown above satisfy the given criteria.

QUESTION: 23

Passage II

An organic compound A(C9H10O) is chiral and does not evolve any gas on treatment with Na-metal but on hydrolysis with dil. H2SO4 gives B (C9H12O2) which on further treatment with alkaline solution of iodine does not give an yellow precipitate. Also A on treatment with excess of conc. HBr gives C (C9H11OBr) as the major product. C on further treatment with C2H5ONa/C2H5OH followed by acidification of product gives D (an isomer of A). D on ozonolysis followed by work-up with dimethyl sulphide gives E (C8H8O2) as one of the product.

Q. 

Which of the following statement regarding B is correct?

Solution:




The compound A shown above satisfy the given criteria.
Shown above, B has a chiral carbon hence, optically active. Moreover, the chiral carbon is not involved in reaction from A to B, configuration would be retained in B.

QUESTION: 24

Passage II

An organic compound A(C9H10O) is chiral and does not evolve any gas on treatment with Na-metal but on hydrolysis with dil. H2SO4 gives B (C9H12O2) which on further treatment with alkaline solution of iodine does not give an yellow precipitate. Also A on treatment with excess of conc. HBr gives C (C9H11OBr) as the major product. C on further treatment with C2H5ONa/C2H5OH followed by acidification of product gives D (an isomer of A). D on ozonolysis followed by work-up with dimethyl sulphide gives E (C8H8O2) as one of the product.

Q. 

The statement that is true regarding A to D is

Solution:




The compound A shown above satisfy the given criteria.
If oxygen of A is labelled as O18, it will be part of phenolic —OH, hence retained in D.

QUESTION: 25

Matching List Type

Direction(Q. Nos. 25-27) 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: 26

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

Solution:




QUESTION: 27

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

Solution:






*Answer can only contain numeric values
QUESTION: 28

One Integer Value Correct Type

Direction (Q. Nos. 28-30) This section contains 3 questions. When worked out will result in an integer from 0 to 9 (both inclusive).

Q. 

An ether, on treatment with sulphuric acid and sodium iodide, yields a single iodoalkane that contains 74.7% iodine by weight. How many carbon atoms are present in a molecule of this ether ? [Molar mass of I = 127]


Solution:

From % of iodine, formula of iodoalkane is derived as C3H7I. Hence, ether is C3H7OC3H7.

*Answer can only contain numeric values
QUESTION: 29

An organic compound A (C10H18O8)on treatment with excess of CH3COCI gives a fully acetylated product whose molar mass is found to be 518 g/mol. How many hydroxyl functional groups are present in A? 


Solution:



Mass gain due to incorporation of one acetyl group = 59 - 17 = 42
Net mass gain due to acetylation = 518 - 266 = 252
Hence, six hydroxy groups (6 x 42 = 252) were present.

*Answer can only contain numeric values
QUESTION: 30

How many different triols would be formed when the following compound is treated with excess of CH3MgBr followed by hydrolysis ?


Solution: