10 Practical Organic Chemistry

SECTION - I : STRIGHT OBJECTIVE TYPE

10.1 Which one of the following will not give white precipitate with ammonical silver nitrate solution
(A) CH3 – C C – CH3 (B) CH3 – CH– C C – CH3

CH3
(C) CH3 – CH2– CH = CH2 (D) All of these

(i) Na metal
No H2 gas evolved
(ii) Cl2/h 3-monochloro
Compound C4H10O
10.2 products
(iii) Lucas reagent
–Ve test
Compound is
O
(A) (B) (C) O (D)
O O

10.3 An aromatic compound A (C8H10O) gives following tests with the given reagents.
Na metal
Positive

FeCl3 (neutral)
A(C8H10O) Negative

Lucas reagent
Positive
Anhydrous ZnCl2/HCl
Identify 'A'
OCH3 OH OH
CH2 – CH2 – OH
CH3 CH2–CH3
(A) (B) (C) (D)
CH3
CH3

10.4 Br2/H2O

Bayer's reagent
C4H6
(X) Na metal

(A) H3C – C C – CH3 (B) CH2 = CH – CH = CH2

C CH
(C) CH3 –CH2 – C CH (D)
10.5 The following two compounds I and II can be distinguished by using reagent
OH HO

COOH COOH
(1) aq. NaHCO3 (2) Neutral FeCI3 (aq.) (FfeCI3 + NH4OH + H2O)
(3) Blue litmus solution (4) Na metal (5) HCI (ZnCI2 anhydrous)
(A) 1 or 3 (B) 2 or 5 (C) 4 or 5 (D) 3 or 4

10.6 Tollen's regent (AgNO3 + NH4OH) can be distinguished between

O O O
O
(A) H–C–H and Ph–C–H (B) H and H H
O O
D O Me
C C=O

(C) and (D) Ph–C–Ph and Me–C–Me

O O
C=O
Me

10.7 Observe the4 following compound and select +Ve & –Ve tests respectively
(i) Na metal

HO C CH (ii) NaHCO3
(iii) 2,4-DNP
OHC COOH
(iv) Lucas reagent

(A) + + + – (B) + + + + (C) + – + – (D) + – – +

10.8 Consider following compounds and decide as to which of the following statements are true ?
CH3 CH3 CH3

CH2 = CH – C – COOH CH3 – C – OCH3 CH3O–C C–H CH3 – C – CH2OCH3

H CH3 OH
(I) (II) (III) (IV)
(A) (II) gives no reaction with Na metal, however, 1 mole of (IV) on reaction with Na metal
willliberate 22.4 litres of H2 gas at STP
(B) (I) will give brisk effervescence on addeition of NaHCO3 but will not bring any change in the
colour of Br2 water
(C) (III) Iiberates H2 gas with Na metal, gives white precipitate with Tollen's reagent but does not
respond towards lucas reagent or 2, 4-DNP test.
(D) (IV) gives turbidity with anhydrous ZnCI2

10.9 An aromatic compound 'X' (C9H8O3) turns blue litmus to red.It gives yellow precipitate with I2/
NaOH and forms Y (C8H6O4).Y forms three mononitro isomeric products. Identify X.
 COCH3 COCH3 COCH3
COOH
(A) (B) (C) (D) none of these
COOH
COOH
10.10 Which will not give iodoform reaction with I2/OH–?
(A) CH3COCH2CH3 (B) CH3CONH2 (C) C6H5COCH3 (D) CH3CHO

10.11 Compound Y1C7H8O is insoluble in water, dil HCI and aqueous NaHCO3.It dissolves in dilute
NaOH. When Y is treated with bromine water it is converted rapidly into a compound of formula
C7H5OBr3.Identfy the structure of Y
OH OH O–H O – CH3
CH3
(A) (B) (C) (D)
CH3
CH3
10.12 Compounds I and II can be distinguished by using reagent
(I) (II)
4-Amino-2-methlbut-3-en-2-ol 4–Amino–2, 2-dimethylbut-3-yn-1-ol.
(A) NaNO2/HCI (B) Br2/H2O
(C) HCI/ZnCI2 (anhydrous) (D) Cu2CI2 + NH4OH

10.13 Compound P(C6H10) does not have any geometrical isomer. ON ozonolysis, two products
R(C3H4O) and Q(C3H6O) are formed. R gives negative iodoform test while Q responds positively
towards I2/NaOH solution. S, another isomer of P is an unsyumetrical alkene and on ozonolysis
produces T(C6H10O2) which also gives a yellow precipitate with I2/NaOH solution and also gives
positive test with Tollen's reagent. Which of the following does not represent any of the molecules
amongst P,Q,R,S&T.
H OO H H OO H
(A) O (B) (C) (D)

10.14 A set of reagents (1 to 8) are successively reacted with the followit compound
O

OH
OH

1. NaHCO3 2.2, 4, DNP 3.Na metal 4. AgNO3 +OH

5. Fehling's solution 6.Cu2CI2 + NH4OH 7. Br2/H2O 8. NaNO2 + HCI
The reagents which give positive test with the given compound are :
(A) 1, 2, 3, 4, 5 (B) 3, 4, 5, 6, 8 (C) 1, 2, 3, 4, 8 (D) All reagents except 1
and 8

10.15 Compounds (C8H8O) X will give following laboratory tests.

Isomers FeCl3 AgNO3 / NH4OH Na metal

X Coloured solution Negative 1/2 H2
 X can be :
H3C O
OCH3 CH2OH OH
O

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

CH = O CHO CH = CH2
OH
10.16 Which of the following alcohol will show positive iodoform test ?
OH OH
(A) CH3 – CH – CH2 – NO2 (B) CH3 – CH– CH2 – COOH

OH
(C) ICH2 – CH – CH2 – CH3 (D) none of these

10.17 The compound A gives following reactions.

Na metal
H2 gas

2, 4-DNP
A(C6H8O2) yellow orange ppt

O3
B(C6H8O4)

Its structure can be

(A) CH2=CH–(CH2)2–C– CH2OH (B) OHC–(H2C)2–HC = HC – COOH
O
OH OH
(C) (D)

O CHO
10.18 In compound A (C30H60O) following tests are observed negatively, A can be :
Br2 / H2O
-Ve
2, 4 DNP
C30H60O -Ve
(A) Na metal
-Ve
(A) an unsaturated ether(B) an epoxide (C) a cyclic ketone (D) a cycloalkanol

10.19 A mixture of two orgnaic compound gives red coloured precipitate with cuprous chloride
(ammonical) and silver mirror on heating with Zn dust and NH4CI followed by AgNO3 + NH4OH
solution. The mixture contains

O COOH COOH
NH2
(A) CH3–(CH2)8–CHO and (B) and

NO2 NH2
CHO CHO CHO
(C) and (D) and
NO2
 SECTION - II : MULTIPLE CORRECT ANSWER TYPE
10.20 2D, 3D, 4D, 5D, 6-Pentahydroxy hexanal can give.
(A) Tollen's Test (B) Lucas Test (C) 2, 4-DNP Test (D) FeCI3 Test

10.21 Compound X and Y both have the same molecular formula (C4H8O). They give following observation
in some lab test.
Test X Y

Br2–water positive negative

Na–metal positive negative
Lucas reagent turbidity after some time negative
lodoform test negative negative
The compound X and Y are

(A) OH (B) OH (C) OH (D) O

10.22 Compound 'P' (C10H12O) evolves H2 gas with Na metal. It reacts with Br2/CCI4 to give 'Q'
(C10H12Br2O). With I2/NaOH it forms iodoform and an acid 'R' (C9H8O2). 'P' has geometrical and
optical isomers. The structure of 'P and R' should be

COOH
(A) (B) PH – CH = CH – COOH

CH=CH2

OH
CH = CH – CH – CH3 CH = CH – CH3
(C) (D)
OH

10.23 compound (X) C9H10O is inert to Br2/CCI4.Vigorous oxidation with hot alkaline KMnO4/OH yields
C6H5COOH. (X) gives precipitate with 2,4-dinitrophenyl hydrazine. How can these isomers be
distinguished by the usual chemical tests?
Following are possible isomkers of X :
(l) C6H5 – CH2 – CH2 – CHO (l) C6H5 – CH – CHO

CH3

O O
(lll) C6H5 – CH2 – C – CH3 (lv) C6H5 – C– CH2 – CH3

(I) C6H5 – CH2 – CH2– CHO

(A) I gives red ppt. with Fehling solution and II & III cand be distinguished by iodoform test
(B) I & II can be distinguished by simple chemical method
(C) I & II give red ppt. with Fehling solution and III & IV can be distinguished by iodoform test
(D) II give red ppt. with Fehling solution and I & IV can be distinguished by iodoform test.

10.24 Which is/are the correct method for separating a mixture of benzoic acid, p-methylaniline &
phenol.
aq.NaHCO3
(A)  aq.NaOH aq.HCI
(B)  aq.NaHCO3
     
aq.NaOH
(C)  aq.NaHCO3 aq.NaOH
(D)  aq.HCI
     
 SECTION - III : ASSERTION AND REASON TYPE
10.25 Statement -1 : Only one Aldehyde 'X' responds positively with all the tests of carbonyl compounds
like Tollen's test, Fehling test, 2, 4-DNP test, as well as iodoform test.
Statement-2 : All aldehydes respond all the four tests given in assertion.
(A) Statement-1 is True, Statement-2 is True; Statement-2 is acorrect explanation for Statement-1.
(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for
Statement-1.
(C) Satement-1 is True, Statement-2 is False.
(D) Statement-1 is False, Statement-2 is True.

10.26 Statement-1 : A mixture os p-methylbenzoic acid and picric acid is separated by NaHCO3
solution .
Statement -2 : p-Methylbenzoic acid is soluble in NaHCO3 because it give effervesence of CO2
(A) Statement-1 is True, Statement-2 is True; Statement-2 is acorrect explanation for Statement-1.
(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for
Statement-1.
(C) Satement-1 is True, Statement-2 is False.
(D) Statement-1 is False, Statement-2 is True.

SECTION - IV : TRUE AND FALSE TYPE

10.27 Give the correct order of initials T or F for following statements. Use T if statement is true and
F if it is false. X (molecular formula, C7H6O2) is and aromatic white solid which liberates
colourless, odourless gas on rescting with NaHCO3.
S1 : Only three of th3e five functional isomers of X (including 'X' itself) will give positive 2, 4-DNP
test.
S2 : The liberated colourles, odourless gas will contaning radioactive 14C.
S3 : Except 'X', no other functional isomer will liberate colourless odourless gas with NaHCO3.
S4 : The DU of higher homolog of 'X' will be four.
(A) TTTF (B) FTTF (C) FTTT (D) TTFF

SECTION - V : COMPREHENSION TYPE

Comprehension # 1
Observe the following sequence of reactions
O3 / Zn,H2O
P (C9H9Br) R + Q
reductive (i) Tollen's Reagent
+
(ii) H

(s) + Ag

P shows geometrical isomersm. Q gives positive Tolen's test and the oxidation product of
Tollen's test followed by acidification is the strongest acid among its all position isomers. R gives
positive lab tests with 2,4-DNP, Fehling solution and I2/NaOH reagents.

10.28 The compound P can be

CH2– CH = CH2 CH= CH – CH3
Br Br
(A) (B)
 CH= CH – CH3
CH= CH – CH3
Br
(C) (C)

Br
10.29 What could be the structure of Q ?
CHO COOH CHO CHO
Br
(A) (B) (C) (D)
Br CH3
CH3
10.30 Identify the structure of R
(A) HCOOH (B) CH3CHO (C) BrCH2 – CHO
Comprehension # 2
An aromatic compound T (C10H10O2) give 2 moles of CHI3 and compound U (C8H4O4Na2) On
treatment with I2 and NaOH. After acidification U gives two mononitro produicts on nitration.

10.31 Compound (T) can aoso be obtained by ozonolysis of V, in this ozonolysis one mole of OHC
– CHO is obtained alongwith (T). Possible structure for Compound V could be
CH3
CH3
CH3

(A) (B)

CH3
CH3
CH3

(C) (D)
CH3

CH3
10.32 Which of the following statement is true
O O
H3 C C CH3
(A) T is C

(B) Compound (V) decolourises pink colour of diluted solution lkof KMnO4.
(C) All isomers (only acidic) of U after acidification gives one mole of CO2 with NaHCO3
(D) After acidification of (U), it is most acidic in its all other isomers.

10.33 Compound U is

COONa COONa COONa COONa

COONa
(A) (B) (C) (D)
COONa
O H COONa
C
||
O
 SECTION - VI : MATRIX - MATCH TYPE
10.34 X(C8H14) by ozonolysis forms Y[C8H14O2]. Y on reaction with NaOI followed by acidification gives
CHI3 and compound Z on strong heating forms W.

Column-I Column-II

(A) Compound X (p) Bayer's Test

(B) Compound Y (q) NaHCO3
(C) Compound Z (r) 2, 4-DNP
(D) Compound W (s) Iodoform Test
(t) Na Metal

10.35 Match the following : (More than one option in column - II may match with single option in
column-I)

Column - I Column - II

C C–H
(A) Sodium metal (X)

O
CH3

C – CH3
(B) Sodium bicarbonate (Y)
OH

C CH
(C) 2, 4-Dinitrophenylhydrazine (Z)
OHC COOH

CH = CH2
(D) Lucas reagent
(W) H3CO
C OH

SECTION - VII : SUBJECTIVE ANSWER TYPE

SHORT SUBJECTIVE :
10.36 A water insoluble organic mixture contained following compounds
(1) = Benzoic acid (2) = salicylaldehyde
(3) = p-Hydroxybenzaldehyde (4) =a-Naphthylamine
(5) = Naphthalene
The following sequence of reagents are uksed to separate this mixture
 1 + 2 + 3 + 4 + 5 mixture

(Step-X) aq. HCI

[Insoluble] [Soluble]*

(Step-Y) aq. NaHCO3

[Insoluble] [Soluble]*

(Step-Z) aq. NaOH

[Insoluble]* [Soluble]

(Step-W) Steam distillation

[distilled]* [left behind]

Fill up the serial number of starred compound ontained in the steps X, Y, Z and W reapectively.
X Y Z W

10.37 How many acidic H is present in given compound.

O OH
O

OH
10.38 How many CHI3 will be released from the given compound.
O O
|| || l2 / NaOH

10.39 How many molecule of phenyIhydrazine is used to form osazone from glucose.
N––NH
CHO
H OH
N––NH
HO H 3Ph–NH–NH2
Hint : HO H + Ph––NH2 + NH3
H OH H OH
H OH OH
H
CH2OH
CH2OH
10.40 How many CHI3 will be released from given compound.
O O
|| ||
H2N OCH3

O
O