ORGANIC CHEMISTRY

TARGET DAILY PRACTICE PROBLEMS

JEE (ADVANCED) : 2014 DPP

COURSE NAME : UMANG (UP) DATE : 02.09.2013 to 07.09.2013 DPP NO. 24

* Marked Questions are having more than one correct option.

DPP NO. # 24
1. Racemic mixture is obtain in which substrate when it is treated with CH3OH

(A) (B) (C) (D)

2. Which of them is correct order for solvolysis rate in aqueous acetone

CH3O–CH=CH–CH2–Cl P

Ph–CH2–Cl Q

CH3O–CH2–CH=CH–Cl R

CH3O–CH2–CH2–CH2–Cl S

(A) R > P > Q > S (B) P > Q > R > S (C) Q > P > S > R (D) P > Q > S > R

3.

P1 and P2 are respectively :

(A) , Br CH2Br (B) , Br

Br

Br Br

(C) , (D) ,
Br Br

NaOH / H O
2
4.* 

Which of the following statements are correct about the above reaction
(A) The reaction is SN1 reaction
(B) The reaction intermediate is carbocation
(C) The major product will be (d+l) mixture of 2,3-dimethylpentane-3-ol
(D) The major product has one stereogenic centre

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A/R
5. Statement-1 : 3-chlorocyclopropene is solvolyzed in methanol at much higher rate than 5-chlorocyclo
penta-1, 3-diene.
Statement-2 : The intermediate carbocation of 5-chlorocyclopenta-1,3-diene is more stable than the
carbocation formed by 3-chlorocyclopropene.
(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

6. Statement 1 : A bridge head halide like norboryl bromide is inert for SN1 reaction

Statement 2 : Carbonium ion at bridgehead position cannot be formed because planarity is not possible.
(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

Subjective
7. Write the correct decreasing order of solvolysis of these halides ?

(a) (I) (II) (III) (IV) (V)

(b) (c)

(d) (e)

ANSWER KEY :
DPP NO. # 24

1. (C) 2. (D) 3. (C) 4.* (ABCD) 5. (C)

6. (A) 7. (a) II > III > I > V > IV ; (b) II > I > III ; (c) III > I > II ; (d) III > I > II (e) II > III > I

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