Subjective Type Questions: Compounds Containing Nitrogen- 2 | JEE Advanced Notes | EduRev

Class 12 Chemistry 35 Years JEE Mains &Advance Past yr Paper

JEE : Subjective Type Questions: Compounds Containing Nitrogen- 2 | JEE Advanced Notes | EduRev

The document Subjective Type Questions: Compounds Containing Nitrogen- 2 | JEE Advanced Notes | EduRev is a part of the JEE Course Class 12 Chemistry 35 Years JEE Mains &Advance Past yr Paper.
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Q.13. Acetophenone on reaction with hydroxylamine hydrochloride can produce two isomeric oximes. Write structures of the oximes.   (1997 - 2 Marks)

Solution.  

Subjective Type Questions: Compounds Containing Nitrogen- 2 | JEE Advanced Notes | EduRev

Q.14. Compound A (C8H8O) on treatment with NH2OH. HCl gives B and C. B and C rearrange to give D and E, respectively, on treatment with acid. B, C, D and E are all isomers of molecular formula (C8H9NO). When D is boiled with alcoholic KOH an oil F (C6H7N) separates out. F reacts rapidly with CH3COCI to give back D. On the other hand, E on boiling with alkali followed by acidification gives a white solid G (C7H6O2). Identify A-G.           (1999 - 7 Marks)

Ans. 

Subjective Type Questions: Compounds Containing Nitrogen- 2 | JEE Advanced Notes | EduRev

Solution. Summarise the given facts.

Subjective Type Questions: Compounds Containing Nitrogen- 2 | JEE Advanced Notes | EduRev

From the above set, following conclusions can be drawn.

(i) Since the oily compound F (C6H7N) reacts with acetyl chloride, it must have - NH2 or > NH group. Thus (F) can be written as C6H5NH2 or C6H5-NH-H, i.e., it is C6H5NH2 and hence D is C6H5NHCOCH3.

Subjective Type Questions: Compounds Containing Nitrogen- 2 | JEE Advanced Notes | EduRev

(ii) Compound E on treatment with alkali followed by acidification gives a white solid compound (G), C7H6O2.
Thus (G) seems to be an acid, hence it is C6H5COOH.

(iii) Since (D) and (E) are isomers of the formula C8H9NO, and give C6H5NH2 and C6H5COOH respectively, both should be amides having different alkyl or aryl group.
Thus (D) should be C6H5NHCOCH3,  and (E) must be CH3NHCOC6H5.

(iv) Since compounds (D) and (E) are formed by the rearrangement of compounds (B) and (C) respectively.
Compounds (B) and (C) should be oximes > C = NOH (recall that oximes rearrange to amides - Beckmann rearrangement). Further oximes having different alkyl (aryl) groups show geometrical isomerism (syn and anti), compounds (B) and (C) must have following structures.

Subjective Type Questions: Compounds Containing Nitrogen- 2 | JEE Advanced Notes | EduRev          Subjective Type Questions: Compounds Containing Nitrogen- 2 | JEE Advanced Notes | EduRev

Recall that Beckmann rearrangement involves migration of anti -alkyl or aryl group, i.e.,

Subjective Type Questions: Compounds Containing Nitrogen- 2 | JEE Advanced Notes | EduRev
Subjective Type Questions: Compounds Containing Nitrogen- 2 | JEE Advanced Notes | EduRev

Since (D) is formed from (B), and (E) from (C), (B) and (C) should have following structures.

Subjective Type Questions: Compounds Containing Nitrogen- 2 | JEE Advanced Notes | EduRev          Subjective Type Questions: Compounds Containing Nitrogen- 2 | JEE Advanced Notes | EduRev

(v) Lastly, oximes (B) and (C) are formed from (A),  the latter should be a ketone of the formula C6H5COCH3,

Subjective Type Questions: Compounds Containing Nitrogen- 2 | JEE Advanced Notes | EduRev


Q.15. Complete the following reaction with appropriate reagents :                 (1999 - 4 Marks)

Solution. 

Subjective Type Questions: Compounds Containing Nitrogen- 2 | JEE Advanced Notes | EduRev
Subjective Type Questions: Compounds Containing Nitrogen- 2 | JEE Advanced Notes | EduRev
Subjective Type Questions: Compounds Containing Nitrogen- 2 | JEE Advanced Notes | EduRev
Subjective Type Questions: Compounds Containing Nitrogen- 2 | JEE Advanced Notes | EduRev|
Subjective Type Questions: Compounds Containing Nitrogen- 2 | JEE Advanced Notes | EduRev

 

Q.16. Explain briefly the formation of the products giving the structures of the intermediates.                 (1999 - 2 Marks)

Subjective Type Questions: Compounds Containing Nitrogen- 2 | JEE Advanced Notes | EduRev   

Solution. The reaction proceeds via benzyne formation        

Subjective Type Questions: Compounds Containing Nitrogen- 2 | JEE Advanced Notes | EduRev

                                  Subjective Type Questions: Compounds Containing Nitrogen- 2 | JEE Advanced Notes | EduRev        


Q.17. How would you synthesise 4–methoxyphenol from bromobenzene in NOT more than five steps? State clearly the reagents used in each step and show the structures of the intermediate compounds in your synthetic scheme.                    (2001 - 5 Marks)

Solution.  

Subjective Type Questions: Compounds Containing Nitrogen- 2 | JEE Advanced Notes | EduRev
      Subjective Type Questions: Compounds Containing Nitrogen- 2 | JEE Advanced Notes | EduRev


Q.18. Write structures of the products A, B, C, D and E in the following scheme.                 (2002 - 5 Marks)

Subjective Type Questions: Compounds Containing Nitrogen- 2 | JEE Advanced Notes | EduRevSubjective Type Questions: Compounds Containing Nitrogen- 2 | JEE Advanced Notes | EduRev

Solution. 

Subjective Type Questions: Compounds Containing Nitrogen- 2 | JEE Advanced Notes | EduRev
Subjective Type Questions: Compounds Containing Nitrogen- 2 | JEE Advanced Notes | EduRev
Subjective Type Questions: Compounds Containing Nitrogen- 2 | JEE Advanced Notes | EduRev
Subjective Type Questions: Compounds Containing Nitrogen- 2 | JEE Advanced Notes | EduRev


Q.19. There is a solution of p–hydroxybenzoic acid and p-aminobenzoic acid. Discuss one method by which we can separate them and also write down the confirmatory tests of the functional groups present.           (2003 - 4 Marks).

Solution. 

Subjective Type Questions: Compounds Containing Nitrogen- 2 | JEE Advanced Notes | EduRev
Subjective Type Questions: Compounds Containing Nitrogen- 2 | JEE Advanced Notes | EduRev
Test of phenolic group :

Subjective Type Questions: Compounds Containing Nitrogen- 2 | JEE Advanced Notes | EduRev

Test of 1°  amino group :

Subjective Type Questions: Compounds Containing Nitrogen- 2 | JEE Advanced Notes | EduRev

Test of – COOH group :

Subjective Type Questions: Compounds Containing Nitrogen- 2 | JEE Advanced Notes | EduRev


Q.20. Identify (A) to (D) in the following series of reactions.             (2004 - 4 Marks)

Subjective Type Questions: Compounds Containing Nitrogen- 2 | JEE Advanced Notes | EduRev

Subjective Type Questions: Compounds Containing Nitrogen- 2 | JEE Advanced Notes | EduRev

Solution. 

Subjective Type Questions: Compounds Containing Nitrogen- 2 | JEE Advanced Notes | EduRev
Subjective Type Questions: Compounds Containing Nitrogen- 2 | JEE Advanced Notes | EduRev
Subjective Type Questions: Compounds Containing Nitrogen- 2 | JEE Advanced Notes | EduRev


Q.21. Subjective Type Questions: Compounds Containing Nitrogen- 2 | JEE Advanced Notes | EduRevSome other products                  (2005 - 4 Marks)

(i) Identify (X) and (Y)
 (ii) Is (Y) optically active?
 (iii) Give structure(s) of intermediate(s), if any, in the formation of (Y) from (X).

Ans. Subjective Type Questions: Compounds Containing Nitrogen- 2 | JEE Advanced Notes | EduRev

Solution. 

Subjective Type Questions: Compounds Containing Nitrogen- 2 | JEE Advanced Notes | EduRev
Subjective Type Questions: Compounds Containing Nitrogen- 2 | JEE Advanced Notes | EduRev

(ii) [Y], a 3° alcohol is optically inactive.

(iii) Formation of [Y] from [X].

  Subjective Type Questions: Compounds Containing Nitrogen- 2 | JEE Advanced Notes | EduRev
Subjective Type Questions: Compounds Containing Nitrogen- 2 | JEE Advanced Notes | EduRev
Subjective Type Questions: Compounds Containing Nitrogen- 2 | JEE Advanced Notes | EduRev

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