XIII (XYZ) ORGANIC CHEMISTRY REVIEW TEST-1

PART-A
Select the correct alternative. (Only one is correct) [26 × 3 = 78]

Q.2 This compound shows:

(A) geometrical isomerism (B) optical isomerism

(C) both (D*) none
[Sol. Cyclohexene do not show geometrical isomerism and the compound given is incapable of showing
optical isomerism]

%Q.5 Give the correct order of initials T or F for following statements. Use T if statement is true and F if it is
false.
I. Me–CH=C=C=CH–Br is optically active.
II. All optically active compound are chiral.
III. All chiral pyramidal molecules are optically inactive.
IV CH3–CH2–CH2–COOH and CH 3  CH  CH 3 are positional isomers.
|
COOH
(A) TTTF (B) FTFT (C*) FTFF (D) TFTT
[Sol. (II) Cyclic chiral pyramidal molecules are optically active.
(IV) CH3–CH2–CH2–COOH and CH 3  CH  CH 3 are chain isomers. ]
|
COOH

Q.8goc Which pairs of the salts should have identical solubilities in methanol?

(I) (II)

(III) (IV)

(A*) I & IV (B) I & III (C) I & II (D) II & IV

[Sol. I & IV are enantiomers, enantiomers have identical solubility]
Q.14 Ph  CH  CHO
|
OH
(A)
(A) & (B) are isomer and isomerization is effectively carried out by trace of base. Identify isomer (B).
O
||
(A) Ph–CH2–CO2H (B) Ph  C  O  CH 3

O O
|| ||
(C*) Ph  C  CH 2  OH (D) H  C  CH 2  O  Ph

[Sol. Ph  CH  CH Ph  C  CH Ph  C  CH 2 ]
| || | | || |
OH O OH OH O OH

Q.1723alkane Sentene ozonolysis

 

Which is the correct structure of Sentene

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

[Sol. + O3   ]
 Question No. 19 to 23 (5 questions)
Alkanes are halogenated in presence of sunlight. The reaction follows free radical mechanism which
completes in three steps.
h
R  H  X 2  RXHX
(i) Chain initiation (fast)
h
X–X  X° + X°
(ii) Chain propogation (slow)
R–H+X° RDS  H–X + R°
R°+X–X  R–X + X°
(iii) Chain termination (fast)
R° + X°  R – X
R°+ R°  R – R
X° + X°  X – X
Rate of this reaction increasing with stability of free radical formed and ease of its formation.
Rate 1° < 2°<3° (for same halogen)
Rate F2 > Cl2 > Br2 > I2 (for same alkane)
If excess of halogen is used one by one all H are replaced by X.

%Q.198alkane Correct order of rate of photochlorination for following compounds is:

CH 3
|
CH3–CH3 CD3–CD3 CH 3  C  CH 3
|
CH 3
(I) (II) (III)
(A*) II < I < III (B) I < II < III (C) III < I < II (D) II < III < I
[Sol. C–D bond is stronger than C–H bond. Neo pentane is 1.15 times more reactive than ethane towards
photochlorination ]
%Q.209alkane If rate determining step of this reaction is chain initiation not chain propogation what will be the
order of rate of reaction for same alkane?
(A*) F2 >Cl2 < Br2 < I2 (B) F2 > Cl2 > Br2 > I2
(C) F2 < Cl2 < Br2 < I2 (D) F2 = Cl2 = Br2 = I2
[Sol. If chain initiation is RDS rate will be decided according to X–X bond energy order. ]

%Q.2110alkane How many possible monochloro products are formed when 2-methoxy propane is treated with
Cl2 in presence of sunlight?
(A*) 4 (B) 3 (C) 2 (D) 1
Cl
* * |
[Sol. ClCH 2  C H  CH 3 ; CH 3  C H  ClCH 2 ; CH  C  CH ; CH 3  CH  CH 3 ]
3 3
| | | |
OCH 3 OCH 3 OCH 3 OCH 2Cl
%Q.2212alkane Total number of chloro derivative possible for ethane is:
(A) 6 (B) 7 (C) 8 (D*) 9
Cl
|
[Sol. (1) C–C–Cl, C–C , (2) Cl–C–C–Cl, (3) C  C  Cl , (4) Cl–C–C ,
|
Cl

(5) C–C , (6) Cl–C– , (7) C– , (8) Cl3C–CCl3]

%Q.23alkene Pick the correct statement for monochlorination of R-secbutyl chloride.

Cl

2
300C

(A) There are four possible products ; three are optically active one is optically inactive
(B) There are five possible products ; three are optically inactive & two are optically active
(C*) There are five possible products ; two are optically inactive & three are optically active
(D) There are four possible products ; two are optically active & two are optically inactive

[Sol. ]

One or more than one is/are correct

Q.27more Which of the following is/are a bicyclo compound(s):

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

[Sol. A is cycloalkyl cycloalkane, B is spiro compound, only C and D are bicyclo compounds ]

%Q.30 Configuration of is

(A*) R (B) S (C*) D (D) L

Q.33 Which of the following is primary amine

(A*) t-butyl amine (B*) aniline (C*) sec. butylamine (D) N-methyl methanamine
[Sol. D is 2° amine]
 MATCH THE COLUMN

%Q.1 Match the column-I with column-II, where column I indicates a pair compound and column II indicates
their relationship. Note that column-I may have more than one matching options in column-II.
[4 × 1 = 4]
Column-I Column-II

(A) & (P) Identical

(B) & (Q) Geometrical isomers

(C) & (R) Diastereoisomers

(D) & (S) Enantiomers

[Ans. (A): Q, R; (B) R; (C) P; (D): R]

%Q.2 Match the column-I with column-II, where column I indicates a compound and column II indicates its
configuration. Note that column-I may have more than one matching options in column-II.
[4 × 1 = 4]
Column-I Column-II

(A) (P) 2R 3S

(B) (Q) S

(C) (R) R

(D) (S) 2S 3R

[Ans. (A): R; (B): Q; (C): P; (D): S]