ORGANIC CHEMISTRY

TARGET DAILY PRACTICE PROBLEMS

JEE (ADVANCED) : 2014 DPP

COURSE NAME : UMANG (UP) DATE : 19.08.2013 to 24.08.2013 DPP NO. 22

1. Which statement is incorrect about the following reaction ?

(A) It undergoes racemisation

(B) It undergoes D-exchange at asymmetric C* atom
(C) Rate of racemisation is equal to rate of D-exchange
(D) The product is laevorotatory

2. STATEMENT -1 : is stronger base than

STATEMENT -2 : The –:NH2 group of (I) is better electron pair donor to H+ ion than the –:NH2 group of (II)
(A) Statement-1 is True, Statement-2 is True; Statement-2 is a correct explanation for Statement-1.
(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for Statement-1
(C) Statement-1 is True, Statement-2 is False
(D) Statement-1 is False, Statement-2 is True
3. Number of 'H' that can takes part in tautomerism in given compound are :

4. Explain why will tautomerise but will not ?

5. Cis and trans-4-tert-butyl-2-methyl cyclohexanone are interconverted by base treatment. Explains why?
6. Arrange the following into decreasing order of percentage enol content :
(i) Ethylacetoacetate (ii) Acetylacetone (iii) Biacetyl (iv) Cyclopentane-1,2-dione (v) Acetone
7. Compound 'X' is acyclic and shows keto enol tautomerism (significant enol content). It is least molecular
weight sweet smelling chiral compound with one 'D' atom which shows positive 2,4-DNP & neutral FeCl3 test.
Calculate its molecular weight.

ANSWER KEY DPP No.22

1. (D) 2. (C) 3. 4 4. Enol of second is antiaromatic.

5. Because of enolisation

6. (iv) > (ii) > (i) > (iii) > (v) 7. Molecular weight = [103]

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