CH 1 The Basics 1

Chapter 1: The Basics: Bonding and Molecular Structure
Practice Problems
1.1
1.2
1.3 (a) ionic (b) ionic (c) covalent (d) covalent
1.4
1.5
Solution Manual for Solomons, Fryhle and Snyder Organic Chemistry For JEE (Main &
Advanced), Copyright©2017 Wiley India Pvt. Ltd. All rights reserved
1.6
1.7
1.8
1.9
1.10
1.11
1.12
1.13
Review Problems
1.14
1.15
1.16
1.17
1.18
1.21
1.22
1.23
1.24
1.25
1.27
<H1> ADDITIONAL OBJECTIVE QUESTIONS
<H2> Single Correct Choice Type
1. (c) It is a germinal halide as both the I are attached to the same C atom.
2. (b) As extent of H bond is: carboxylic acid>alcohol.
3. (a) 2o carbons are C atoms attached directly to two other C atoms.
4. (c) II is not an acceptable structure as N can only accommodate a maximum of 8 electrons in the
cationic state.
5. (b) DBE=4 ; No. of C (C) = 10.
DBE = (C+1) – (H)/2. Solving the equation for H, we get, H = 14
6. (b) HC≡C-CH=CH2. The molecule has 3 pi bonds and 7 singma bonds (3 between C-C and 4 between C-
H).
7. The question numbering is repeated and also the question is WRONG!! No option is correct.
8. (c) is most stable due to resonance of anion and the electron withdrawing effect of nitro
group.
9. (d) I and III are more stable than II and IV due to resonance stabilization of the cation with the lone
pair of O and formation of octet complete carbocation. I is more stable than III due to higher degree of
carbocation. Similarly, II is more stable than IV due to higher degree of carbocation.
10. (d) Here the molecules shown are geometrical isomers about the left pi bond.
11. (d) An additional atom is present (H on N) which is not allowed in resonance structures.
12. (c) I and IV are not resonance structures as the H atom is moved and moving of atoms is not allowed
in resonance.
13. (c) I and II are more stable resonating structures as they have an additional pi bond as compared to III
and IV. II is more stable than I as it has the negative charge on N as compared to C. III is more stable than
IV due to the negative charge on N as compared to C.
14. (d) It has an additional covalent pi bond in addition to complete octet of all the atoms.
15. (b) Tertiary butyl carbocation [ (CH3)3C+ ] is the most stable of the given carbocations due to the
maximum number of hyperconjugable alpha H atoms.
16.
16. (b) As the delocalization is only between the two pi bonds on the right, the pi bond on left is not in
conjugation.
17. (d) It is resonance stabilized and it also has the highest degree.
18. (a) I, II and IV are the most stable free radicals as they are resonance stabilized and the stability
order amongst them is based on the number of resonating structures. Amongst III,V and VI, higher the
degree of free radical, greater is its stability.
19. (d) The sp C has two pi bonds while the sp3 C has no pi bonds.
20. (d) The first carbocation is more stable due to resonance.
21. (a) In carbocation, hyperconjugation is between σ and empty p orbital of carbocation. While in
alkene, hyperconjugation is between σ and π* orbital of the alkene.
22. (d) I is most stable due to two equivalent RS while II is also resonance stabilized anion. IV is more
stable than III due to lesser extent of destabilizing +I effect of alkyl upon anion.
23. (b) z has the highest bond length of the three as it has purely single bond character. Y has more
single bond character than x due to higher stability and contribution of the neutral RS as compared to the
charged RS.
<H2> Multiple Correct Choice Type
1. (b), (d) In b, H atom is moved while moving of atoms is not allowed in resonance. In d, the second
molecule has an extra atom (C atom), while atoms cannot be added or subtracted in resonance.
2. (a), (d) In resonance structures, only electrons are allowed to be moved and not atoms as in II where
H atom is moved. Also the number of paired and unpaired electrons must remain same, which is not the
case in III.
<H2> Linked-Comprehension Type
1. (b) I, II and IV are resonance stabilized carbocations due to resonance between the carbocation and
lone pair of N. The stability order amongst them is on the basis of degree of carbocation, higher the
degree, higher the stability of carbocation. III is least stable as there is no resonance stabilization in it.
2. (a) I and II are more stable than III and IV due to one extra covalent pi bond in them. I is more stable
than II as I is a neutral RS. III is more stable than IV as in III, negative charge is on more electronegative
O atom.
3. (b) It will not show resonance as the pi bonds are not in conjugation.
4. (d) The carbocation and pi bond must be at alternate position for them to be in conjugation.
5. (c) There is resonance amongst the pi bonds present between C1-C2 and C3-C4, thus these bonds will
have a character between a single and a double bond. While C6-C7 have a pure double bond between
them, which is not in resonance, thus it has a lower bond length than C3-C4.
<H2> Integer Type
1. (4) The positive charge is delocalized on 4 carbon atoms due to resonance.
2. (6) Consider the benzene ring as a system and then see the hydrogen atoms present at adjacent
(alpha) position to it. There is one H atom each on each of the six alpha C atoms.
<H2> Matrix Match Type
1.
(a)→(p), (q) Resonance is between the lone pair and pi bond. Numbering for IUPAC name starts from the C atom
attached to alcohol functional group.
(b)→(p), (r) Resonance is between the lone pair and pi bond. Numbering for IUPAC name starts from the C atom
attached to alcohol functional group.
(c)→(s) No resonance as no conjugation. IUPAC name is 4-chlorocyclobutenol.
(d)→(s) No resonance as no conjugation. IUPAC name is 1-chlorocyclobut-2-enol.

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Chapter 1: The Basics: Bonding and Molecular Structure

1.3 (a) ionic (b) ionic (c) covalent (d) covalent

<H1> ADDITIONAL OBJECTIVE QUESTIONS

<H2> Single Correct Choice Type

3. (a) 2o carbons are C atoms attached directly to two other C atoms.

5. (b) DBE=4 ; No. of C (C) = 10.

DBE = (C+1) – (H)/2. Solving the equation for H, we get, H = 14

20. (d) The first carbocation is more stable due to resonance.

<H2> Multiple Correct Choice Type

<H2> Linked-Comprehension Type

<H2> Integer Type

1. (4) The positive charge is delocalized on 4 carbon atoms due to resonance.

<H2> Matrix Match Type

(c)→(s) No resonance as no conjugation. IUPAC name is 4-chlorocyclobutenol.

(d)→(s) No resonance as no conjugation. IUPAC name is 1-chlorocyclobut-2-enol.

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