(Organic Chemistry) Rankers Group

SECTION - 1
1. The product " X " in the following reaction is

(A) a racemic mixture of ester (B) an optically inactive ester

(C) an optically active ester (D) a meso ester
2. The sequence of reagents required for the following conversion is

(A) (i) B2 H6 /H2 O2 /OH − (ii) Na (iii) C2 H5 I (B) (i) HCl (ii) C2 H5 ONa
(C) (i) H3 O+ (ii) Na (iii) C2 H5 OH (D) (i) H3 O+ (ii) Na (iii) C2 H5 Cl
3. Compound ' X ' in the following reaction is

(A) (B)

(C) (D)
4. The order of pK a values of the following acids is

(A) IV > I > III > II (B) III > IV > I > II
(C) II > I > III > IV (D) II > III > I > IV

APNI KAKSHA 1
5. The major product of the following reaction is

(A) (B)

(C) (D)
6. Compound X(pK a ∼ 15) and Y(pK a ∼ 10), both produce H2 one treatment with sodium metal
and both yield a mixture of isomers on mononitration. X and Y respectively are:

(A) IV, I (B) III, II (C) III, I (D) I, III

7. The monosaccharide present in the following disaccharide is

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

APNI KAKSHA 2
8. The IUPAC name of the following compound is

(A) 1 - Bromo - 4 − chloro -3 etheny ibutane

(B) 4 - Bromon -1 - chloro -3 ethenylbutane
(C) 3 − (Bromomethyl) -5 - chloropent - 1 - ene
(D) 3 − ( Bromomethyl) −1 − chloropent -4 - ene
9. The correct order of boiling points of the following compounds is

(A) III < IV < II < I (B) I < III < IV < II
(C) I < II < III < IV (D) IV < III < I < II
10. Compound ' P ' that undergoes the sequence of reactions given below to give the product Q is

(A) (B)

(C) (D)

APNI KAKSHA 3
11. The correct sequence of reagents from those listed below for the following conversion is-

(I) NaNH2 (II) Br2

(III) H2 /Pd − C, quinoline (IV) H3 O+
(A) IV - I – III (B) III −IV − I
(C) II − I − III (D) I - II – III
12. The compound ' X ' undergoing the following reaction is

(A) (B)

(C) (D)
13. The major product of the following reaction is

(A) (B)

(C) (D)
APNI KAKSHA 4
 SECTION - 2
1. An organic compound (A) C5H9Br, which readily decolourise Br2 water and KMnO4 solution
gives (B), C5H11Br on treatment with Sn/HCl. The reaction of [A] with NaNH2 produces [C]
with evolution of ammonia. (C) neither reacts with Na nor forms any metal acetylide but reacts
with lindlar catslyst to give [D] and on reaction with Na/liq, NH3 produces [E]. Both [D] and [E]
are isomeric. Give structure of [A] to [E] with proper resonating.
2. An organic compound (A), C7H7Cl gives two isomeric mononitro derivatives (B) and (C). (A)
does not give a ppt with alcoholic AgNO3 but on oxidation with KMnO4 gives [D] C7H5O2Cl
which on heating with sodalime gives C6H5Cl. On treatment with KNH2 in liquid NH3 (A) gives a
mixture of isomeric products E (minor) and F (major) of formula C7H9N. Both [E] and [F] can be
diazoxised and coupled with alk. naphtol. [E] but not [F] on diazotizationand warming with
CuCl gives back (A). Give structures of all and explain the formation of [E] and [F] from [A].
3. A hydrocabron (A) , of the formula C8H10, on ozonolysis gives compound (B) C4H6O2 only. The
compound (B) can also be obtained from the alkyl bromide (C), C3H5Br upon treatment with Mg
in dry ether followed by CO2 and acidification. Identify (A), (B) and (C) and also gives equations.
4. An organic compound ‘A’ C10H12O gives red color when treated with cerric ammonium nitrate
solution and also decolourizes bromine water in carbon tetra chloride to give an addition product
‘B’.C10H12OBr2 ‘A’ can show both geometrical and optical isomerism. ‘A’ on treatment with 12
in NaOH gives iodoform and an acid ‘C’ after acidification. Give the structures of ‘A’ to ‘C’ and
also all the stereoisomers of ‘A’.
5. An organic compound ‘A’ (C15H13ON) decolourises Bayer’s reagent. On strong oxidation ‘A’
given 2 acids ‘B’ and ‘C’ which are separated by fractional crystallization. ‘B’ provide bernzoic
acid and ‘C’ is an important industrial product used for the manufacturing of terylene. Deduce the
structures of ‘A’, ‘B’ and ‘C’.

APNI KAKSHA 5
 SECTION - 3
1. Find the unknowns.

APNI KAKSHA 6
 ANSWER KEY
SECTION - 1
1. (C) 2. (D) 3. (C) 4. (D) 5. (C) 6. (D) 7. (A)
8. (C) 9. (B) 10. (B) 11. (C) 12. (C) 13. (A)

APNI KAKSHA 7