Chapter 20

Organic Chemistry :
Some Basic Principles and Techniques

Only One Option Correct Type Questions

1. The number of structural isomers for C6H14 is [IIT-JEE-2007 (Paper-1)]
(A) 3 (B) 4
(C) 5 (D) 6
2. Among the following, the least stable resonance structure is [IIT-JEE-2007 (Paper-2)]

 O O
 
(A) N (B)  N
| |
O O

O O

(C) 
N (D) 
N


| |
O O

3. Sodium fusion extract, obtained from aniline, on treatment with iron (II) sulphate and H2SO4 in presence of air gives
a Prussian blue precipitate. The blue colour is due to the formation of [IIT-JEE-2007 (Paper-2)]

(A) Fe4[Fe(CN)6]3 (B) Fe3[Fe(CN)6]2

(C) Fe4[Fe(CN)6]2 (D) Fe3[Fe(CN)6]3

4. Hyperconjugation involves overlap of the following orbitals [IIT-JEE-2008 (Paper-1)]

(A) – (B) –p

(C) p – p (D) –

5. The correct stability order for the following species is [IIT-JEE-2008 (Paper-2)]

I. 
O

II. 


III.
O

IV.


(A) (II) > (IV) > (I) > (III) (B) (I) > (II) > (III) > (IV)
(C) (II) > (I) > (IV) > (III) (D) (I) > (III) > (II) > (IV)

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6. The correct acidity order of the following is [IIT-JEE-2009 (Paper-1)]

OH OH COOH COOH

Cl CH3
(I) (II) (III) (IV)
(A) (III) > (IV) > (II) > (I) (B) (IV) > (III) > (I) > (II)
(C) (III) > (II) > (I) > (IV) (D) (II) > (III) > (IV) > (I)

7. The IUPAC name of the following compound is [IIT-JEE-2009 (Paper-1)]

OH

CN
Br
(A) 4-Bromo-3-cyanophenol (B) 2-Bromo-5-hydroxybenzonitrile
(C) 2-Cyano-4-hydroxybromobenzene (D) 6-Bromo-3-hydroxybenzonitrile
8. In the following carbocation, H/CH3 that is most likely to migrate to the positively charged carbon is
[IIT-JEE-2009 (Paper-2)]
H H
1 + 5
2 4
H3C—C —C—C
3
—CH3

HO H CH3
(A) CH3 at C-4 (B) H at C-4
(C) CH3 at C-2 (D) H at C-2
9. The correct stability order of the following resonance structures is [IIT-JEE-2009 (Paper-2)]
 –  –
I. H2C  N  N II. H2 C— N  N
–  – 
III. H2 C— N  N IV. H2 C— N  N
(A) (I) > (II) > (IV) > (III) (B) (I) > (III) > (II) > (IV)
(C) (II) > (I) > (III) > (IV) (D) (III) > (I) > (IV) > (II)
10. Which one of the following structures has the IUPAC name 3-ethynyl-2-hydroxy-4-methylhex-3-en-5-ynoic acid?
[IIT-JEE-2020 (Paper-1)]

OH

(A) CO 2H (B) HO 2C
OH

OH OH

(C) CO 2H (D) CO 2H

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11. Among the following, the conformation that corresponds to the most stable conformation of meso-butane-2,3-
diol is [JEE (Adv)-2021 (Paper-1)]

OH OH
H Me H OH

(A) (B)
Me H H Me
OH Me

OH OH
Me OH H OH

(C) (D)
H Me Me H
H Me

One or More Option(s) Correct Type Questions

12. The correct statement(s) concerning the structures E, F and G is (are) [IIT-JEE-2008 (Paper-1)]
O H3C OH H3C CH3
H3C

H3C CH3 H3C CH3 H3C OH

(E) (F) (G)

(A) E, F and G are resonance structures
(B) E, F and E, G are tautomers
(C) F and G are geometrical isomers
(D) F and G are diastereomers
13. Amongst the given options the compound(s) in which all the atoms are in one plane in all the possible
conformations (if any), is(are) [IIT-JEE-2011 (Paper-1)]

H H H
(A) C—C (B) H—C C—C
H 2C CH2 CH2
(C) H2C = C = O (D) H2C = C = CH2
14. Which of the following molecules, in pure form, is (are) unstable at room temperature? [IIT-JEE-2012 (Paper-1)]

(A) (B)

O
O

(C) (D)

15. The hyperconjugative stabilities of tert-butyl cation and 2-butene, respectively, are due to [JEE (Adv)-2013 (Paper-1)]
(A)   p (empty) and   electron delocalisations
(B)  * and   electron delocalisations
(C)   p (filled) and   electron delocalisations
(D) p (filled)  and   electron delocalisations

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16. The IUPAC name(s) of the following compound is(are) [JEE (Adv)-2017 (Paper-1)]

H3C Cl

(A) 1-chloro-4-methylbenzene (B) 4-chlorotoluene

(C) 1-methyl-4-chlorobenzene (D) 4-methylchlorobenzene
17. With respect to the compounds I-V, choose the correct statement(s). JEE (Adv)-2020 (Paper-1)]

H
H CH3
I II III

H H
IV V
(A) The acidity of compound I is due to delocalization in the conjugate base
(B) The conjugate base of compound IV is aromatic
(C) Compound II becomes more acidic, when it has a -NO2 substituent
(D) The acidity of compounds follows the order I > IV > V > II > III
Integer / Numerical Value Type Questions
18. The total number of cyclic structural as well as stereoisomers possible for a compound with the molecular
formula C5H10 is [IIT-JEE-2009 (Paper-2)]
19. The total number of cyclic isomers possible for a hydrocarbon with the molecular formula C4H6 is
[IIT-JEE-2010 (Paper-1)]
20. The total number of contributing structures showing hyperconjugation (involving C-H bonds) for the following
carbocation is [IIT-JEE-2011 (Paper-2)]
H3C CH2CH3
+

21. The number of resonance structures for N is [JEE (Adv)-2015 (Paper-1)]

OH
NaOH
N

22. Among the following, the number of aromatic compound(s) is [JEE (Adv)-2017 (Paper-1)]

+ +

  

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