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Test Organic Chemistry (25!11!2023)
Test Organic Chemistry (25!11!2023)
ORGANIC CHEMISTRY
(for JEE-Mains & Advanced 2025)
Time : 2 : 30 Hr. Max. Marks :416
* Each question + 4 (for correct answer) & - 1 (for wrong answer)
=============================================================================================================
01. Benzene on reaction with allyl chloride in presence of anhyd. AlCl3 gives (A), which
on ozonolysis gives (B) and (C). The DBE of (B) is ‘n1’ and that of (C) is ‘n2’ {n1> n2}.
(A) on reduction with H2–Ni gives (D).
Which of the following is correct :
CH2
(a) (A) is Ph–C and n1 + n2 is 6.
CH3
(b) (A) is PhCH2CH=CH2 and n1 & n2 both are odd numbers.
(c) Position iosmer of (A) is PhCH=CHCH3 and n1 – n2 is equal to DBE of (D).
(d) Both (b) and (c).
02. PhCH2COOH on heating with sodalime gives (A) and PhCH2CH2COOH on heating with
sodalime gives (B)
Which of the following is correct.
(a) (A) on reaction with Br2/Fe gives PhCH2Br
(b) (B) on reaction with Br2/hv gives PhCH2CH2Br
(c) (A) on reaction with Conc. HNO3/Conc. H2SO4 gives product at faster rate as
compared to that of (B) in the same reaction.
(d) (A) on reaction with hot alkaline KMnO4 gives different product than the product
obtained on reaction of (B) with hot alkaline KMnO4.
Br Br
Br
(a) (b) (c) (d)
Br
COOH
Me NO2
Br Br NO 2
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13. If the mixture of the following four aromatic compounds on oxidation by strong
oxidising agent gives :
, , and
(IV)
(I) (II) (III)
(a) I > II > III > IV (b) II > III > IV > I
(c) III > II > IV > I (d) II > III > I > IV
15. Benzene on treatment with neopentyl chloride in presence of AlCl3 gives :
(a) neopentyl benzene (b) t—pentyl benzene
(c) sec—pentyl benzene (d) isopentyl benzene
16. PhCOOH
NaOH (CaO)/heat Br2 /Fe
Mg/ ether
(A)
(A)
Methyl alcohol
Product is :
(a) Toluene (b) Phenol (c) anisole (d) benzene
COOPh
17. In the attack of NO2+ results in the formation of :
+ (2 mole)
H2 SO4
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O
(B)
C
19. (A) N The bromination takes place at :
(D)
CH2
(C)
SO3 H COOH
Me Me
(A) gives H2 gas on reaction with Na and (B) on Clemmensen reduction gives (C). (A)
on reaction with Br2/ H2O gives CxHyOBrz. (C) is :
+ _
NH3 Cl NO2
NH2 NH——
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Me
Ph
O—OH
NO2 Me
(a) PhOH + p–cresol (b) PhOH + p–nitrophenol
(c) MeOH + p–cresol (d) MeOH + p–nitrophenol
+
25. HO CN i)
K2S2O8/ KOH ii) H3O
Product is :
HO
HO
HO HO
HO
OH
OH OH
OH HO
OH
O
OH
26. HNO
2 Product is :
NO2
OH OH OH OH
O2 N NO2 NO
ON NO
27. Among the following compounds how many produce violet colour with neutral FeCl3
OH
(A) Phenol, (B) Aspirin, (C) oil of wintergreen (D) Salol , (E)
O——H-----O
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28. Benzaldehyde undergoes Perkin reaction with a reagent (A) in presence of (B) to give
compound (C). (A), (B), (C) are :
Ph
C = C——COOH
(a) (Ph CH2 CH2 CH2 CO)2 O , Ph CH2 CH2 CH2 COOK , CH2 CH3
O O Me
CH=CH— —COOH
(b)Me– – C –O– C – –Me , ,
COONa
O OK
(c) . ,
Me Me Me
O COONa
(d) , , .
29. The intermediate (I) in Etard oxidation of toluene contains ‘x’ no. of ‘O’ atoms. In the
preparation of DDT chlorobenzene is treated with a reagent (R) in presence of conc.
H2SO4. The no. of ‘Cl ‘ atoms in (R) are :
(a) x — 1 (b) x (c) x + 1 (d) x2
F Br
_
30. Br on reaction with MeO K+ gives :
NO2
H
F
OMe OMe
H
(a) (b)
MeO
Br
NO2
NO2
F H OMe H
MeO
(c) Br (d) Br
NO2 NO2
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NO2
31. i)
Zn—HCl ii) NaOH iii) NaNO2/ HCl; cold —naphthol
(A)
NO2
+ _ _
i)
Sn/ HCl ii) NaNO2/ H2SO4 iii) steam
PhN2 Cl / OH
(B)
NO2
i)
Br2 / Fe ii) TiCl3 / HCl iii) Ac2O
Br
2/ CH3COOH
(C)
OH Br
N=N— NHAc
N=N
OH
(a) , ,
Br
N2 Ph
32. (NH
(A) Ac
4)2 S
2O
(B) ; (B) Conc. (C)
HNO3/ Conc. H2SO4
(C) is :
NHAc NHAc NO2 NHAc NHAc NO2
NO2 NHAc
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34. n-hexane can be prepared by hydrogenation of ‘X’ number of isomeric alkynes of
formula CyH2y – 2 of which (A) is the terminal alkyne.
Na , alkyl bromide
(A) , NaBr + (C)
(B)
(B) on Wurtz coupling reaction gives (D). (C) and (D) are :
(a) n–BuCC–CH2CH2CH=CH2 , CH2 = CH(CH2)4 CH = CH2 , x + y is equal to DBE of
biphenyl methane.
(b) n–PrCH2CC–CH2CH2CH2CH=CH2 , CH2 = CH(CH2)6 CH = CH2 , x + y is equal to
DBE of Anthracene.
(c) CH3CH2CH2CH2–C C–CH2CH2CH=CHCH3 , CH3CH=CHCH2(CH2)4CH2CH=CHCH3
, x + y is equal to DBE of C30H42NClBr2O5 .
(d) CH3CH2(CH2)2CC–CH2CH2CH2CH2CH=CH2 , CH2 = CH(CH2)8CH=CH2 , x + y is
equal to DBE of C40H60N2Cl4Br2O8 .
35. The attacking reagents in the reactions
R1 : CH3 CH2 CH = CH2 + BrCl
R2 : CH3 CH2 CH = CH2 + HCl , peroxide are :
+
(a) Br , H +
(b) Br , Cl
+
(c) Br , H+ (d) Br , Cl
36. During mutarotation of -D-glucose in aqueous solution angle of optical rotation
(a) Remains constant value of + 111° (b) Remains constant value of + 19.2°
(c) Changes from an angle of +112° to a constant value of +52.5°
(d) Changes from an angle of +19.2° to a constant value of +52.5°
37. Which of the following is correct about cellulose?
(a) It is an important food material
(b) It has only -glycosidic linkage between two D-glucose unit
(c) It has only -glycosidic linkage between two D-glucose unit
(d) It is sweet in taste
38. Which of the following is an essential amino acid?
(a) Asparagine (b) Glutamine (c) Histidine (d) Alanine
39. Peptides are composed of amino acids joined by amide bonds. which of the follow-
ing statements is not correct ?
(a) Amide group are more resistant to hydrolysis than one similar ester groups
(b) p- resonance stabilizes the amide bond
(c) Stable conformations of peptides are restricted to those having planar amide
groups
(d) Amide groups do not participate in hydrogen bonding interaction
40. Complementary bases present in DNA are :
(a) Uracil & Adenine : Cytosine & Guanine
(b) Thymine & Adenine : Guanine & Cytosine
(c) Adenine & Thymine : Guanine & Uracil
(d) Adenine & Guanine : Thymine & Cytosine
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41. Which of the following statements would correctly describe the isoelectric point of
cysteic acid an oxidation product of cysteine ?
(a) Lower than that of aspartic acid (b) About the same as that of aspartic acid
(c) About the same as that of Cysteine (d) Higher than that of lysine
42. Dinucleotide is obtained by joining two nucleotides together by phosphodiester link-
age. Between which carbon atoms of pentose sugar of nucleotides are these link-
ages presents.
(a) 5' and 3' (b) 1' and 5' (c) 5' and 5' (d) 3' and 3'
43. Which of following are essential amino acids–
(1) Aspartic acid (2) Leucine (3) Valine (4) Glycine (5) Alanine
(a) 1, 2 & 3 (b) 1, 2, 4 & 5 (c) 2 & 3 (d) 1, 3, 4 & 5
44. A single stand of DNA can act as a template on which a molecule of RNA is synthe-
sized in a specific manner. This process is known as :
(a) Replication (b) Transcription (c) Translation (d) Denaturation
45. Column-I (Reaction of Glucose) Column-II (Product)
HI ,
(a) Glucose (p) Osazone
Br2 water
(b) Glucose (q) n-Hexane
Nitric Acid
(c) Glucose (r) Gluconic acid
3Ph–NH–NH 2
(d) Glucose (s) Saccharic acid
H
(a) a – q, b – s, c – p, d - r (b) a – q, b – p, c – r, d - s
(c) a – q, b – s, c – r, d - p (d) a – q, b – r, c – s, d - p
46. Column-I (Carbohydrates) Column-II (Monosaccharide unit)
(a) Maltose (p) -D-Glucose
(b) Lactose (q) Two -D-Glucose
(c) Cellulose (r) -D-Galactose & -D-Glucose
(d) Sucrose (s) -D-Glucose & - D-Fructose
(a) a – q, b – s, c – r, d - p (b) a – q, b – r, c – p, d - s
(c) a – r, b – s, c – p, d - q (d) a – r, b – p, c – q, d - s
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47. Which of the following statements are correct?
( i) Lact ose is a -galactoside.
(ii) The -carbon of all 20D-amino acids of proteins except cysteine has R-configu-
ration.
(iii) In Killiani –Fischer synthesis,arabinose gives equimolar mixture of glucose
and mannose .
(iv) On oxidation with nitric acid, arabinose gives an opticallly active dicarboxylic
acid .
(a) Only (ii) and (iii) (b) Only (i) ,(iii) and (iv)
(c) Only (i) ,(ii) and (iv) (d) Only (i) and (iii)
48. Both cysteine and methionine are chiral L-amino acids that incorporate a single
sulfur. The C-2 configuration is S in methionine, but R in cysteine. Why ?
(a) biosynthesis of cysteine proceeds by inversion at C-2.
(b) the sulfur in cysteine prevents zwitterion formation.
(c) the sulfur atom in methionine is remote from C-2 and does not influence the
sequence rule.
(d) the sulfur atom in cysteine is remote from C-2 and does not influence the se-
quence rule.
49. A hexapeptide has the composition Ala,Gly,Phe,Val3. Both the N-terminal and C-
terminal units are Val. Cleavage of the hexapeptide by chymotrypsin gives two dif-
ferent tripeptides, both having Val as the Nterminal group. Among the products of
random hydrolysis is a Ala-Val dipeptide fragment. What is the primary structure of
the hexapeptide ?
(a) Val-Gly-Phe-Val-Ala-Val (b) Val-Ala-Phe-Val-Gly-Val
(c) Val-Gly-Ala-Val-Phe-Val (d) Val-Phe-Val-Ala-Gly-Val
50. The structure of the product that results when piperidine reacts with pentanal fol-
lowed by catalytic reduction with H2 is :
(a) N (b) N
O---H-O O
C6H5
(I)
N (II)
C=O
O O O--HO
OH--O
C6H 5 CHO C6H5
(III) (IV) N
C6H5 H
O
(a) I (b) II (c) III (d) IV
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Comprehension : (Q. No 52 to 59)
There are two vessels V1 & V2. In V1 vessel two different alkyl chlorides (A) and (B) are
present in presence of ether. In vessel V2 two different alkyl chlorides (C) and (D) are
present in presence of ether. The difference in molecular weights of (A) & (B) is d1 and
difference in molecular weights of (C) & (D) is d2. The value of d1 is greater than d2. Na
is introduced in both the vessels. Wurtz coupling reaction occurs resulting in formation
of alkanes (E), (F), (G) in vessel V1 and (E), (H), (I) in vessel V2. (E) can be prepared by
Sabatier—Senderens hydrogenation of an alkene (J) .
(J) HBr/
peroxide
(K) Na
/ ether
n—decane.
Answer the following questions :
52. (F) is : (a) Propane (b) n–butane (c) n–pentane (d) n–octane
53. (G) is : (a) ethane (b) n–butane (c) n–hexane (d) n–pentane
54. The value of d1 is :
(a) 14 (b) 28 (c) 42 (d) 56
55. The value of d2 is :
(a) 14 (b) 28 (c) 42 (d) 56
56. (H) and (I) are :
(a) ethane, n-butane (b) ethane, n-hexane
(c) n-butane, n-octane (d) n-hexane, n-butane
57. (J) on treatment with Cl2/CCl4 gives :
(a) CH3CH2CHClCHClCH3 (b) CH3CHClCH2CH2CH2Cl
(c) CH3CH2CH2CHClCH2Cl (d) CH3CH2CHClCH = CH2
58. (F) can be prepared by Wurtz coupling reaction of an alkyl bromide (L). (L) on treat-
ment with alc. KOH gives
(a) 2–butene (b) 1–butene (c) 1–hexene (d) propene
59. The no. of isomeric alkenes whose hydrogenation result in the formation of (E) are :
(a) 1 (b) 3 (c) 4 (d) 2
Comprehension fir Q. no. 60 to 62
Mild oxidizing agents, e.g. bromine water, Tollen’s regent, Fehling’s solution etc., oxi-
dize aldoses into aldonic acids. Both glucose and fructose can be oxidized by Tollen’s
reagent and Fehling’s solution despite the presence of a keto group in fructose. Strong
oxidizing agents like conc. HNO3 oxidizes glucose to a dibasic acide (saccharic acid).
Fructose under similar condidtions is also oxidized. Both glucose and fructose can be
reduced by red P/HI, LiAlH4 , Clemmensen and Wolff-Kishner reduction.
60. Which of the following cannot be oxidized by bromine water?
(a) D-arabinose (b) D-glyceraldehyde (c) L-glucose (d) L-fructose.
61. One mole of each of glucose and fructose require x and y moles of periodic acid re-
x
spectively, for oxidation. Hence .
y
1 2 5 9
(a) (b) (c) (d)
1 1 4 4
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62. When one mole of D-arabinose is oxidized by periodic acid, the product (s) formed is
(are) :
(a) 5 moles of HCOOH (b) 4 moles of HCOOH and one mole of HCHO
(c) 3 moles of HCOOH and 2 moles of HCHO (d) 5 moles of HCHO
Multiple Choice Type #
CH2
01. (R) on reaction with HBr/peroxide gives a product (P). Which of the
D
following is/are correct ?
(a) (R) but not (P) show geometrical isomerism.
(b) (P) but not (R) show geometrical isomerism.
.
(c) (P) is primary alkyl halide. (d) The attacking reagent is Br
CH3 CH2
02. (R) on reaction with excess HBr/peroxide gives (P).
Me Me Cl Me CH2Cl
Cl
(a) (b) (c) (d)
Cl
05. Which of following compound will show geometrical isomerism ?
Me Me
(a) (b) (c) Cl (d)
Me
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08. Geometrical isomer is shown by :
(a) (b)
(c) (d)
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15. Geometrical isomerism is shown by :
H Cl CH2 CHCl
(a) H (b) (c) (d)
Br H Cl H Cl
16. In which of the following order of stability of alkene is correct :
17. When D-Glucose reacts with three moles of phenylhydrazine it forms glucosazone.
Which of the following carbohydrates will give same osazone as that of D-Glucose?
(a) (b)
(c) (d)
(a) (b)
(c) (d)
24. For "invert sugar", the correct statement(s) is/are (Given : Specific rotations of
(+)-sucrose, (+)-maltose, L-(–)-glucose and L-(+)-fructose in aqueous solution are
+66°, +140°, –52° and +92°, respectively)
(a) "Invert sugar" is prepared by acid catalyzed hydrolysis of maltose
(b) "Invert sugar" is an equimolar mixture of D-(+)-glucose and D-(–)-fructose
(c) Specific rotation of "invert sugar" is –20°
(d) On reaction with Br2 water, "invert sugar" forms saccharic acid as one of the
products
25. The Fischer presentation of D-glucose is given below.
(D-glucose)
CH=CH2
Me Me
are ‘n1’ and the number of geometrical isomers of are ‘n2’ .
Et Et
Calculate the value of (n1 + n2) ?
03. The number of geometrical isomeric pairs obtained on photomonochlorination of
methyl cyclohexane are n1 and the number of structural isomers obtained on
photomonochlorination of neohexane are n2. Calculate the value of |2n1 – 3n2|
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04. 3,3-dimethyl cyclohexene on reaction with Cl2/hv gives a mixture of two isomeric
products (A) and (B).
Photomono
(A) H2 – Ni (P) ‘n1’ no. of isomeric dichlorides.
Chlorination
Photomono
(B) H2 – Ni (Q) ‘n2’ no. of isomeric dichlorides.
Chlorination
(Consider only structural isomers) (n1 > n2)
alc. KOH
(P) (R) {contains ‘n3’ no. of H – C hyperconjugated bonds }
Heat
alc. KOH
(Q) (S) {contains ‘n4’ no. of H – C hyperconjugated bonds }
Heat
4
05. How many geometrical isomer are possible for the given compound ?
06. The double bond equivalent of Buckminster fullerene is 'n1' and the no. of cyclic
structures of C5H10 are 'n2'. Calculate the value of (n1 + n2).
07. How many geometrical isomers are possible for the following structure.
H
08. Consider the following compounds :
SO3 H SO2 R C Cl3 COOR +
NH3 OCOR NHCOR
In How many compounds the electrophilic attack takes place at m—position ?Ans:5
09. Consider the following statements :
(P) —NH2 is more activating than —NHCOCH3
(Q) —OH is more activating than —NH2
(R) —CCl3 is activating while —Cl is deactivating
(S) —Cl is activating but —CCl3 is deactivating
How many are correct ?
10. A decapeptide (Mol. Wt. 796) on complete hydrolysis gives glycine (Mol. Wt. 75),
alanine and phenylalanine. Glycine contributes 47.0% to the total weight of the hy-
drolysed products. The number of glycine units present in the decapeptide is ?
11. Calculate the sum of nitrogen atoms in one molecule each of Guanidine , Arginine,
Guanine, Cytosine, Cysteine, Methyl orange.
12. Among the following compounds
(i) Adenine (ii) -D-Ribose (iii) Mesitylene (iv) Barbituric acid
(v) Ascorbic acid (vi) Carpolactum
How many are heterocyclic .
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