SINHA IIT CHEMISTRY 1

JEE-SIMILAR TEST.
GOC and Alkane.
INSTRUCTIONS
A . General
1. T his booklet is your Question Paper containing 27 questions.
2. Fill in the boxes provided below on this page and also w rite your Name and R egistration No. in the space
provide on the back page of this booklet.
3. T he answe sheet, a machine-readable Objective Response Sheet (ORS), is provided separately.
4. DO NOT TAMPER WITH/MULTILATE THE ORS OR THE BOOKLET.
5. Do not break the seals of the question-paper booklet before being instructed to do so by the invigilators.
B . Filling the OR S :
6. On the lower part of the ORS, write in ink, your name in box L1, your Registration No. in box L2 and Name of the
Centre in box L3. Do not write these anywhere else.
7. Write your Registration No. in ink, in the box L 4 provided in the lowerpart of the ORS and darken the appropriate
bubble UNDER each digit of your Registration No.with a good quality H B pencil.
8. The ORS has a CODE printed on its lower and upper parts.
9. Make sure the CODE on the ORS is the same as that on this booklet and put your signature in ink in box L5 on the
ORS affirming that you have verified this.
10. IF THE CODES DO NOT MATCH , ASK FOR A CHANGE OF THE BOOKLET.
C . Question paper format :
D . Marking scheme
11. For each question in Section I , you will be awarded 3marks if you darkened only the bubble to the correct answ
er and zero mark if no bubble is darkened. In all other cases, minus one (–1) mark will be awarded.
12. For each question in Section II , you will be awarded 4 marks if you darkened all the bubble(s) to the correct
answer and zero mark for all other cases. It M ay be noted that there is nonegative marking for wrong answ er.
13. For each question in Section III , you will be awarded 3 marks if you darken only the bubble to the correct answ
er and zeromark if no bubble is darkened.In all other cases, minus one (-1) mark will be awarded .
14. For each question in Section IV , you will be awarded 3 marks if you darken only the bubble to the correct
answer and zero mark if no bubble is darkened. In all other cases, 0 mark will be awarded .
15. For each question in Section V , you will be awarded 6 marks if you give the correct answer . In all other cases, 0
mark will be awarded .

SECTION - I
Straight Objective Type
This section contains 6 multiple choice questions. Each question has 4 choices (A), (B), (C) and
(D),out of which ONLY ONE is correct.

1. The terpene ocimene has the IUPAC name (3E)-3,7-dimethyl-1,3,6-octatriene, what is the structural
formula of this compound?

2. Which of the following dimethylcyclobutanes is chiral ?

A) trans-1,2-dimethylcyclobutane B) cis-1,2-dimethylcyclobutane
C) trans-1,3-dimethylcyclobutane D) cis-1,3-dimethylcyclobutane

3. The radical halogenation of 2-methylpropane gives two products: (CH3)2CHCH2X (minor) and (CH3)3CX
(major)
Chlorination gives a larger amount of the minor product than does bromination, Why?
A) Bromine is more reactive than chlorine and is able to attack the less reactive 3° C-H.
B) Bromine atoms are less reactive (more selective) than chlorine, and preferentially attack the weaker 3°
C-H bond.
C) The methyl groups are more hindered to attack by the larger bromine atom.
D) Bromination is reversible and the more stable 3°-alkyl bromide is formed exclusively.

4. Which of the following is not an electrophile?

A) C2H5OC2H5 B) BF3
(+)
C) [CH3]3C D) HOCl

5. Considering that the angles of a regular pentagon are 108°, why is cyclopentane not planar?
2
A) all the carbons are sp hybridized, so there is considerable angle strain.
B) The C-C bonds are formed by overlap of p-orbitals, so the 90° angle results in large angle strain.

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 SINHA IIT CHEMISTRY 2 JEE-SIMILAR TEST.
C) The cyclic overlap of bonding orbitals results in anti-aromaticity destabilization.
D) The C-H bonds have eclipsing strain.
6. . Which of the following isomeric hexenes will have the smallest heat of hydrogenation?
A) 4-methyl-1-pentene. B) (E)-4-methyl-2-pentene.
C) (Z)-4-methyl-2-pentene. D) 2-methyl-2-pentene.
………………………………………………………………………………………………………
Section - II
Multiple Correct Answer Type
This section contains 4 multiple choice answer(s) type questions. Each question has 4 choices
(A), (B), (C) and (D), out of which ONE OR MORE is/are correct.
…………………………………………………………………………………………………………………………..
7. Which of the following compounds has two or more conjugated double bonds?

8 The monochloroisomer that forms in the mixture resulting from the free radical chlorination of
CH3CH2CH2CH=CH2 is
A).ClCH2CH2CH2CH=CH2 B).CH3CHClCH2CH=CH2 C).CH3CH2CHClCH=CH2
D)..CH3CH2CH2CCl=CH2
-
9 Which anion is more basic than OH ?
1- 1- 1- 1-
A). C2H5O B).NO3 C) CN D).CH3COO
10.Which of the amines listed below would have the H bonding.?
A). CH3CH2CH2NH2 B).CH3CH2NHCH3 C).(CH3)3N D).(CH3)3CNH2
……………………………………………………………………………………………………………….
SECTION - III
Reasoning Type
This section contains 4 reasoning questions. Each question has 4 choices (A), (B), (C) and (D) out
of which ONLY ONE is correct.
…………………………………………………………………………………………………………………………..
11.STATEMENT-1 :Benzene and 1,3-butadiene ,both are conjugated species.
STATEMENT-2 : both Benzene and 1,3-butadiene gives baeyers reagent test.
(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
© Statement-1 is True, Statement-2 is False
(D) Statement-1 is False, Statement-2 is True
12.STATEMENT-1 : Benzyne has high energy and highly reactive.
STATEMENT-2 : Benzyne is aromatic.
(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
© Statement-1 is True, Statement-2 is False
(D) Statement-1 is False, Statement-2 is True
13.STATEMENT-1 :All cis compounds can be Z also.
STATEMENT-2 : cis -2-butene can be written as Z-2-butene.
(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
© Statement-1 is True, Statement-2 is False
(D) Statement-1 is False, Statement-2 is True
14.STATEMENT-1 :2-methyl-1-butene is more stable than 2-methyl-2-butene
STATEMENT-2 : alkane is thermodynamically more stable than alkene.
(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
© Statement-1 is True, Statement-2 is False
(D) Statement-1 is False, Statement-2 is True
…………………………………………………………………………………………………………………………..
SECTION – IV
Linked Comprehension Type
This section contains 3 paragraphs C61-63, C64-66 and C67-69. Based upon each paragraph, 3
multiple choice question have to be answered. Each question has 4 choices (A), (B), (C) and (D),
out of which ONLY ONE is correct.
…………………………………………………………………………………………………………………………..
Paragraph-1Confirmational Isomer

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 SINHA IIT CHEMISTRY 3
JEE-SIMILAR TEST.
In a sample of cyclohexane, the two identical chair conformers are present in equal concentration, and
the hydrogens are all equivalent (50% equatorial & 50% axial) due to rapid interconversion of the
conformers. When the cyclohexane ring bears a substituent, the two chair conformers are not the same.
In one conformer the substituent is axial, in the other it is equatorial. Due to steric hindrance in the axial
location, substituent groups prefer to be equatorial and that chair conformer predominates in the
equilibrium.
We noted earlier that cycloalkanes having two or more substituents on different ring carbon atoms exist
as a pair (sometimes more) of configurational stereoisomers. Now we must examine the way in which
favorable ring conformations influence the properties of the configurational isomers. Remember,
configurational stereoisomers are stable and do not easily interconvert, whereas, conformational isomers
normally interconvert rapidly. In examining possible structures for substituted cyclohexanes, it is useful to
follow two principles.
 Chair conformations are generally more stable than other possibilities.
 Substituents on chair conformers prefer to occupy equatorial positions due to the
increased steric hindrance of axial locations.

15. Which of the following isomers has the lowest heat of combustion?
A) cis-1,2-dimethylcyclohexane B) trans-1,2-dimethylcyclohexane
C) cis-1,3-dimethylcyclohexane D) trans-1,3-dimethylcyclohexane

16. Which of the following conformational structures is 2-methylpentane ?

17. . The preferred conformation of cis-1,3-dimethylcyclohexane is ...

A) chair—diaxial B) chair—diequatorial
C) chair--one axial / one equatorial D) boat--mixed orientations

Paragraph-2
Cleavage of C=C with ozone to give two carbonyl compounds is called ozonolysis.

18. . A C8H12 chiral hydrocarbon, X, is reduced by catalytic hydrogenation to an achiral C8H14 compound.
Ozonolysis of X (H2O2 workup) gave a chiral C8H12O4 dicarboxylic acid. Which of the following could be X
?

19. Two C5H8 isomers undergo catalytic (Pt) hydrogenation to form the same C5H10 product. On
ozonolysis followed by oxidative workup (H2O2), one isomer gave a C5H8O4 diacid, while the other isomer
gave a C5H8O3 ketoacid.Which of the following isomeric pairs correspond to this evidence?
A) cyclopentene and 1-pentyne B) cyclopentene and 1-methylcyclobutene
C) 1-methylcyclobutene and 3-methylcyclobutene
D) cyclopentene and 3-methylcyclobutene

20. A C6H12 compound reacts with ozone to yield a single C3H6O product. Gas phase free radical
bromination of the hydrocarbon gives a single C6H11Br product. A likely identification of this compound is.
A) cyclohexane B) cyclohexene
C) 3-hexene D) 2,3-dimethyl-2-butene

Paragraph-3
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 SINHA IIT CHEMISTRY 4 JEE-SIMILAR TEST.
Isomer
Isomerism occurs when two or more compounds have the same molecular formula but at least two
different physical or chemical properties due to some structural or spatial difference in molecular
structure. The different molecules are known as isomers. The existence of isomers is one of the reasons
why such a huge array of different organic compounds exist
1. Structural Isomerism:Structural isomerism occurs when two or more compounds have the same
molecular formula but different structural formula. At least one atom is bonded to a different atom in each
molecule when isomers are compared.
Five main sub-divisions of structural isomerism, (a) to (e), are considered below.-
(1a) Chain isomerism (1b) Positional isomerism (1c) Functional group isomerism (1d) Tautomerism
(1e) Metamerism.

21. Which of the following structures would be considered an enol tautomer of cyclopentanone?

22. Which isomer of hexane has only two different sets of structurally equivalent hydrogen atoms.?
A) 2,2-dimethylbutane B) 2-methylpentane
C) 3-methylpentane D) 2,3-dimethylbutane

23. Limiting your answer to cycloalkanes and ignoring stereoisomers, how many C6H12 constitutional
isomers are there?
A) 6 B) 9 C) 11 D) 13
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SECTION - IV
Matrix Match Type
This section contains 2 questions. Each question contains statements given in two columns which have to
be matched. Statements (A, B, C, D) in Column-I have to be matched with statements (p, q, r, s) in
column-II.The answers to these questions have to be appropriately bubbled
24.
Column-I column-II.
A. iodination of propane P. Free radical mechanism.
B. chlorination of propane Q. above 90% 20 halo product
C. bromination of propane R. reversible
S. overall endothermic.

25.
Column-I column-II.
A. methyl amine P. most solvated.
B. Dimethylamine Q. most +I effect.
C. Trimethyl amine R. least basic.
S. most basic.
SECTION - V
This section contains 2 questions. The answer must be written in answer box.
26. : Arrange the following compounds in order of resonance energy and briefly explain your reasoning.

27. .Identifying an Unknown Alkane

A saturated hydrocarbon burns in oxygen to give carbon dioxide and water. Approximately twice as much
CO2 as H2O (by weight) is produced by this combustion, the actual factor being 2.03.
Light induced chlorination of the hydrocarbon by 2.0 equivalents of chlorine gives a mixture of mono-, di-
and trichloro compounds, along with small amounts of higher chlorination products. Only one monochloro
isomer is formed, but there are two dichloro isomers and three trichloro isomers produced in the reaction.
Based on this information, identify the hydrocarbon, and draw structural formulas for the chlorinated
compounds.Find the molecular formula of the hydrocarbon also ?

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