Organic Chemistry

IIT-JAM Chemistry — General Organic Chemistry and Reaction Mechanisms previous year questions

21 questions · 2005 · all with verified answer · last checked 2026-11-10

Q1 · 2005-2022 · 2 marks

Arrange the following in the decreasing order of acidity of the hydrogen indicated in italic (i) \mathrm{CH}_{3} \mathrm{COCH}_{3} (ii) \mathrm{CH}_{3} \mathrm{COCH}_{2} \mathrm{COCH}_{3} (iii) \mathrm{CH}_{3} \mathrm{OOCCH}_{2} \mathrm{COOCH}_{3} (iv) \mathrm{CH}_{3} \mathrm{COCH}_{2} \mathrm{NO}_{2}

(a) (ii) > (iii) > (i) > (iv)
(b) (iv) > (ii) > (iii) > (i)
(c) (iv) > (iii) > (ii) > (i)
(d) (ii) > (iv) > (iii) > (i)

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Answer: (b)

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Q2 · 2005-2022 · 2 marks

The value of 'n' for the following molecule according to Huckel's rule is

(a) 16
(b) 4
(c) 3
(d) 14 IIT JAM 2008

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Answer: (c)

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Q3 · 2005-2022 · 2 marks

Which of the following are aromatic? P Q R S

(a) P and Q
(b) Q and R
(c) R and S
(d) Q and S

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Answer: (d)

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Q4 · 2005-2022 · 2 marks

Electrophilic nitrations of the following compounds follow the trend P Q R S

(a) S . R>P>Q
(b) R > S > P > Q
(c) R > P > S > Q
(d) P > S > R > Q

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Answer: (b)

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Q5 · 2005-2022 · 2 marks

The Correct order of stability of the following carbonium ions is (I) (II) (III)

(a) II > I > III
(b) III > II > I
(c) I > II > II
(d) II > III > I IIT JAM 2014

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Answer: (d)

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Q6 · 2005-2022 · 2 marks

The homolytic breaking of the \mathrm{C}_{\mathrm{a}}-\mathrm{C}_{\mathrm{b}} bond is easiest in:

(a)
(b)
(c)
(d) IIT JAM 2015

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Answer: (d)

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Q7 · 2005-2022 · 2 marks

Among the following, the number of molecules that are aromatic is ____ . Structure for this question

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Answer: 3

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Q8 · 2005-2022 · 2 marks

The correct order of pKa for the following compounds is (I) Structure for this question

(II) (III) (IV) Structure for this question

(a) II > I > III > IV
(b) II > I > IV > III
(c) III > IV > I > II
(d) IV > II > I > III

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Answer: (b)

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Q9 · 2005-2022 · 2 marks

The compound that contains the most acidic hydrogen is

(a) \mathrm{H_2C{=}CH_2}
(b) \mathrm{CH \equiv CH}
(c) \mathrm{H_2C{=}C{=}CH_2}
(d) \mathrm{H_3C{-}CH_3}

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Answer: (b)

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Q10 · 2005-2022 · 2 marks

For the reaction shown below if the concentration of KCN is increased four times, the rate of the reaction will be :

(a) doubled
(b) increased four times
(c) unaffected
(d) halved

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Answer: (c)

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Q11 · 2005-2022 · 2 marks

The reaction of (+) 2-iodobutane and \mathrm{NaI} * (I* is radioactive isotope of iodine) in acetate was studied by measuring the rate of racemization \left(\mathrm{k}_{\mathrm{r}}\right) and the rate of incorporation of \mathrm{I}^{*}\left(\mathrm{k}_{\mathrm{i}}\right).

(+) \mathrm{CH}_{3} \mathrm{CH}(\mathrm{I}) \mathrm{CH}_{2} \mathrm{CH}_{3}+\mathrm{NaI}^{*} \rightarrow \mathrm{CH}_{3} \mathrm{CH}\left(\mathrm{I}^{*}\right) \mathrm{CH}_{2} \mathrm{CH}_{3}+\mathrm{NaI}

For the reaction, the relationship between \mathrm{k}_{\mathrm{r}} and \mathrm{k}_{\mathrm{i}} is:

(a) \mathrm{k}=2 \times \mathrm{k}
(b) \mathrm{k}=(1 / 2) \times \mathrm{k}
(c) \mathrm{k}=\mathrm{k}
(d) \mathrm{k}=(1 / 3) \times \mathrm{k}

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Answer: (b)

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Q12 · 2005-2022 · 2 marks

\mathrm{R}(-)2–Bromooctane on treatment with aqueous \mathrm{KOH} mainly gives 2-octanol that is:

(a) Optically active with ‘R’ configuration
(b) Optically active with ‘S’ configuration
(c) A racemic mixture
(d) A meso compound

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Answer: (b)

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Q13 · 2005-2022 · 2 marks

The major product obtained in the following reaction

(a)
(b)
(c)
(d)

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Answer: (a)

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Q14 · 2005-2022 · 2 marks

The structure of the major product in the following reaction is: Structure for this question

(a)
(b)
(c)
(d) IIT JAM 2015

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Answer: (d)

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Q15 · 2005-2022 · 2 marks

The correct order of rate of solvolysis for the following compound is I II III

(a) III > II > I
(b) II > I > III
(c) III > I > II
(d) II > III > I IIT JAM 2020

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Answer: (d)

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Q16 · 2005-2022 · 2 marks

The rate of nitration of the following aromatic compounds decreases in the order (i) benzene (ii) pyridine (iii) thiophene (iv) toluene

(a) (iv) > (i) > (iii) > (ii)
(b) (iii) > (iv) > (i) > (ii)
(c) (iii) > (ii) > (i) > (iv)
(d) (ii) > (i) > (iv) > (iii) IIT JAM 2006

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Answer: (b)

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Q17 · 2005-2022 · 2 marks

The major product of the following reaction Structure for this question

(a)
(b)
(c)
(d)

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Answer: (d)

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Q18 · 2005-2022 · 2 marks

Alliong une ionow ing me major piouuct ovidined in hie reaction beiow is.

(a)
(b)
(c)
(d)

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Answer: (d)

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Q19 · 2005-2022 · 2 marks

The number of possible monoalkylated products formed in the Friedel-Crafts reaction of anisole with 2-chloro- 3-methylbutane in the presence of anhydrous \mathrm{AlCl}_{3} at 50^{\circ} \mathrm{C} is ____ IIT JAM 2016

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Answer: 4

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Q20 · 2005-2022 · 2 marks

The correct set of reagents for the following conversion is Structure for this question

(a) (i) \mathrm{NaNH}_{2} / liq. \mathrm{NH}_{3}; (ii) \mathrm{NaNO}_{2} / dil. HCl ; (iii) CuCN , heat
(b) (i) \mathrm{HNO}_{3} / \mathrm{H}_{2} \mathrm{SO}_{4}; (ii) \mathrm{Zn} / \mathrm{HCl}; (iii) \mathrm{NaNO}_{2} / dil. HCl ; (iv) CuCN , heat
(c) (i) \mathrm{Mg} / ether, \mathrm{H}_{2} \mathrm{O}^{+}; (ii) (\mathrm{EtO})_{2} \mathrm{CO}; (iii) \mathrm{NH}_{4} \mathrm{OH}; (iv) \mathrm{PCl}_{5}
(d) (i) \mathrm{Mg} / ether, \mathrm{H}_{2} \mathrm{O}^{+}; (ii) \mathrm{HNO}_{3} / \mathrm{H}_{2} \mathrm{SO}_{4}; (iii) \mathrm{NaNO}_{2} / dil. HCl ; (iv) CuCN , heat IIT JAM 2018