Chapter 5: Nomenclature and Conformations of Alkanes and Cycloalkanes

Practice Problems

5.1

5.2
5.3

5.4
5.5

5.6
5.7
5.8

5.9
5.10

5.11
5.12

5.13
5.14

5.15
5.16

5.17

5.18
5.19

5.20
5.21
5.22

5.23

5.24
5.25

5.26

5.27
5.28

5.29
5.30

5.31

5.32
5.33
5.34

5.35

5.36
5.37
<H1> ADDITIONAL OBJECTIVE QUESTIONS

<H2> Single Correct Choice Type

1. (a) In b,c,d the longest chain has not been chosen as the parent chain.

2. (d) Longest chain is of 8 members.

3. (a) Numbering would start from left as per lowest locant rule.

4. (d) Isopropyl group is [ (CH3)2CH- ].

5. (c) Both gauche and anti lies at energy minima on the graph.

6. (b) Numbering would start from the carbon of ring with which the methyl substituent is attached and
would then continue along the pi bond.

7. (c) It represents the most stable anti-conformer of 1-iodo-2-methylpropane.

8. (d)

9. (b) Numbering would start from the left as in case of tie between double and triple bond in
numbering, double bond is given preference as per IUPAC nomenclature rules.

10. (c) Bulky group at equatorial position is more stable and here the tertiary butyl group which is more
bulky should preferably at equatorial, Thus reactant would be favored at equilibrium.

11. (a) Triheptacontane indicates 73 carbon atoms.

12. (d) II has more steric strain than I due to the bulky groups methyl coming close in gauche conformer.

13. (c) Numbering starts from the C atom to which the OH group is attached.

14. (b) Both the methyl groups are in the axial position.
15. (b) Most stable is gauche due to H bond between the OH group and F.

16. (a) Phenol has OH group attached to benzene directly.

17. (b) Only one of the two substituents can be at equatorial position as the groups are attached in trans
configuration. Hence the more bulky group tert-butyl should be at equatorial.

18. (a) As per IUPAC rules for naming of complex substituents.

19. (c) On the basis of H bonding between OH and F groups and on the basis of steric factor.

20. (c) For isomers, heat of combustion is inversely proportional to stability. C is least stable due to high
angle strain in cyclopropyl rings.

21. (b) Neopentane is (CH3)4C.

22. (c) More the number of C atoms, more is the heat of combustion.

23. (c) As they are geometrical isomers , therefore, cannot be interconverted at room temperature due
to pi bond.

24. (c) More the number of C atoms, more is the heat of combustion.

25. (b) Both can be interconverted by rotation about the sigma bond.

<H2> Multiple Correct Choice Type

1. (a) (c) sec-butylalcohol is 2-butanol while neo-pentyl alcohol is 2-methylpropan-1-ol.

<H2> Integer Type

1. (4) Parent chain would be the acyclic part as it contains the main functional group ketone and
numbering would be from the right.

<H2> Matrix Match Type

1. (a)(r); (b)(s) ; (c)(p); (d)(q)

Naming as per IUPAC rules. In numbering, alkene is given preference over substituents.

2.