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IIT – JEE: 2024 TW TEST (ADV) DATE: 10/08/23

TIME: 1 Hr. TOPIC: HYDROCARBON MARKS: 80

Section – I : Single Answer Correct Type

This section contains 05 multiple choice questions. Each question has 4 options (A), (B), (C) and
(D) for its answer, out of which ONLY ONE option can be correct.
Marking scheme: +4 for correct answer, 0 if not attempted and –1 in all other cases.

21. Which of the following is chiral?

(a) trans–1, 2–dimethylcyclobutane (b) cis–1, 2–dimethylcyclobutane
(c) trans–1, 3–dimethylcyclobutane (d) cis–1, 3–dimethylcyclobutane

22. Pick out correct statement?

CH
CH CH
3
3 3

X2
+
x
H C CH
H C
H C CH
3 3
3 3

x
3

I
II
(a) If X = Cl, II is major & I is minor product
(b) If X = Br, I is major & II is minor product
(c) If X = Br, I & II are formed in equal ratio
(d) If X = Cl, I is major & II is minor product

23. Hydroboration – oxidation of 1–methylcyclohexene gives

(a) 1–methylcyclohexanol (b) cis–1–methylcyclohexan–1, 2–diol
(c) cis–2–methylcyclohexanol (d) trans–2–methylcyclohexanol

24. The sequence of reactions to prepare 1 – deuteropropane from propane is

(a) NBS/HBr ; alcoholic KOH; BH3 in THF/ H3CCOOD
(b) NBS/HBr ; alcoholic KOH; BD3 in THF/H3CCOOH
(c) NBS/HBr ; Mg in ether / ; D2O
(d) NBS/HBr ; alcoholic KOH, H2O + Hg(OAc)2 / NaBD4

25. Which of the following alkene on reductive ozonolysis gives only acetone (propanane)
(a) 2–butene (b) 2, 3–dimethyl–2–butene
(c) Isobutene (d) 2–methyl–2–pentene

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 Section – II : Multiple Answer(s) Correct Type
This section contains 10 multiple choice questions. Each question has 4 choices (A), (B), (C)
and (D) for its answer, out which ONE OR MORE is/are correct. (+4, –2)
Partial Marks: +1 For darkening a bubble corresponding to each correct option. Provided NO
incorrect option is darkened. In all other cases, minus (–2) mark will be awarded in these parts.
For Example: If (A), (C) and (D) are all the correct options for a question, darkening all these
three will result in +4 marks; darkening only (A) and (D) will result in +2 marks; and
darkening (A) and (B) will result in –2 marks, as a wrong option is also darkened.

26. Which of the following statement(s) are true regarding the bromination of alkanes?
(a) It is more selective and less reactive then chlorination
(b) In the transition state carbon has more free radical character
(c) T.S. resemble more of products than reactants
(d) It is less selective and more reactive than chlorination

27. Total number of products formed are (including stereoisomers)

CH

mono chlorination

(a) 10 (b) 9 (c) 4 (d) 8

28. Which of the following acids sodium salt aqueous solution on electrolysis gives 2, 3–dimethyl
butane?
(a) butanoic acid (b) 2–methyl propinoic acid
(c) 2–methyl butanoic acid (d) Propaonic acid

29. Which of the following free radial reactions are possible in monochlorination of CH4
(a) CH3  Cl   H3C.+ HCl (b) .CH3  Cl2   H3C Cl + Cl.
(c) Cl.  Cl2 
 Cl2 + Cl. (d) .CH3  CH4 
 CH4 +.CH3

30. 3, 3–dimethyl–2–butanol  conc.H2SO4


 . Pick out correct statement(s).
(a) It is a single step reaction
(b) It involves carbon skeleton rearrangement
(c) It involves carbocation intermediate
(d) It involves first order rate determining step

31. Meso–butane–2, 3–diol can be prepared by reacting

(a) cis–2–butene with alkaline KMnO4
(b) Trans–2–butene with mCPBA followed by H3O+
(c) cis–2–butene with mCPBA followed by H3O+
(d) trans–2–butene with alkaline KMnO4

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32. A C8H14 (x) is reduced by sodium in liquid ammonia to give a product Y (C8H16). Both of these
compounds undergo catalytic hydrogenation to form 2, 5–dimethyl hexane. Ozonolysis of Y with
oxidative work up produces a single C4H8O2 carboxylic acid. Reaction of Y with perbenzoic acid
(C6H5CO3H) gives a chiral (C8H16O), but reaction with Br2/CCl4 gives an achiral (C8H16Br2) product.
X and Y are
(a) X is 2, 5–dimethyl–3–hexyne
(b) X –2, 5–dimethyl–1, 5–hexadiene
(c) Y is trans–2, 5–dimethyl–3–hexene
(d) Y is cis–3, 5–dimetyl–3–hexene

33. Chiral hydrocarbon (C8H12) X, is reduced by catalytic hydrogenation to an achiral C8H14 compund.
Oxidative ozonolysis of ‘X’ gave a chiral C8H12O4 (Dicarboxylic acid). Which of the following
would be the ‘X’.

(a) H C

3 (b) H C

H C

(c) (d)

34. The best reagent to prepare only 3–methyl but–2–ol from 3–methyl but–1–ene is
(a) H2O in presence of H3O+ (b) alkaline KMnO4
(c) BH3 in THF + alkaline H2O2 (d) H2O + Hg(OAc)2 and NaBH4

35. Methane is obtained by reacting CH3MgBr with

(a) H2O (b) C2H5OH (c) HC  CH (d) C6H5NH2

Section – III : Numerical Value Type

This section contains 5 questions. Each question is numerical value type. For each question,
enter the correct numerical value (e.g. 6.25, 7.00, –0.33, –.30, 30.27, –127.30).
Marking scheme: +4 for correct answer, 0 if not attempted and 0 in all other cases.

36. Number of isomeric hexanes are ______

37. Total number of isomers possible for C4H8 are__________

38. Number of hyper conjugated (no bond resonance) structures contribute to the stability of major
product of below reaction are
CH

conc. H2SO4
OH
H C

3


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39. Total no of products formed in below reaction (including streo isomers) are
CH

2
NBS / HBr
H C

40. Number of products (including stereo isomers) formed in below reaction are

mono chlorination
U.V. light

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 MUMBAI / DELHI-NCR / PUNE / NASHIK / AKOLA / GOA / JALGOAN / BOKARO / AMRAVATI / DHULE
IIT – JEE: 2024 TW TEST (ADV) DATE: 10/08/23
TOPIC: HYDROCARBON

21. (a) 22. (d) 23. (d) 24. (a) 25. (b)

26. (abc) 27. (a) 28. (b) 29. (abcd) 30. (abcd)

31. (ab) 32. (ac) 33. (a) 34. (d) 35. (abcd)

36. (5) 37. (6) 38. (9) 39. (4) 40. (5)

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