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

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.

What is the major product of the following reaction?

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?

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 ?

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

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

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 ?

What is the major product of the reaction?

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 ?

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

Compounds which on reduction can produce alcohols is/are

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

Q. 

The correct statement regarding the above test is/are

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

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

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

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?

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?

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?

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

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?

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

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.

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

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

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]

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? 

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