W1-2-60-1-6

JOMO KENYATTA UNIVERSITY OF AGRICULTURE AND TECHNOLOGY

UNIVERSITY EXAMINATIONS 2017/2018
YEAR I SEMESTER I EXAMINATION FOR THE DEGREE OF BACHELOR OF SCIENCE IN
PUBLIC HEALTH
SCH 2108: ORGANIC CHEMISTRY
DATE: DECEMBER 2017 TIME: 2 HOURS
INSRUCTIONS: ANSWER ALL QUESTIONS IN SECTION A AND ANY ONE QUESTION
IN SECTION B

1. Explain the following terms as used in organic chemistry.

a. Homologous series. (2 marks)

b. Functional group (2 marks)

c. Nucleophile. (2 marks)

2. Use the compound below to answer the questions that follow

a. State the type of hybridization exhibited by carbons a, b and d. (3 marks)

b. Explain the type of hybridization exhibited by carbon labeled b. (3 marks)

3. Xylitol Ii is a naturally occurring alcohol widely used as a sugar substance in chewing

gums and candies.

|OH
HOCH 2 CH −CH −CH −CH 2 OH II
| |
OH

a. Draw the bond line or zig zag structure of compound II. (2 marks)

b. Name compound II using IUPAC system. (2 marks)

c. State and explain the physical state of compound II at room temperature.

 (2 marks)

4. Explain the following classes of organic compounds

a. Alphatic compounds (2 marks)

b. Alicyclic compounds (2 marks)

c. Aromatic compounds. (2 marks)

5. Penicilin G has the moleculr formula C16 H18 N2 O4S.

a. Explain the term molecular formula. (2 marks)

b. Calculate the double bond equivalence of penicillin G. (Valency C=4, H=1, N=3,
O=2 and S=2) (4 marks)

6. Using structures explain the following

a. Methanol is more polar than acetone. (3 marks)

b. Methanol is more soluble in water than acetone. (3 marks)

7. a. Draw the resonance structures of benzene. (2 marks)

b. Describe the orbital structure of benzene. (4 marks)

8. Nitrobenzene has been used as an ingredient in shoe polish but found to penetrate the
skin with harmful effects.

a. Draw the structure of nitrobenzene showing clearly te ortho, meta and para positions.
(3 marks)

b. Using an equation explain nitration of benzene. (3 marks)

SECTION B (22 MARKS)

a. Chloro ethane is used as a general anaethetic administered by inhalation

i. In reference to chloro ethane explain the terms heteroatom and prefix. (3 marks)

ii. Draw the Lewis structure of chloro ethane showing clearly the dipole moment. (atomic
number H=1 C=6 CL=17) (3 marks)

iii. Describe the preparation of chloroethane using ethanol stating clearly the reagents.
(4 marks)

b. Discuss the primary and secondary types of chemical bonding in organic compounds.
(8 marks)
c. Provide the IUPAC names of the following compounds including stereochemistry.

(2 marks) (2 marks)

10. a. Explain with the help of structures the following types of bicyclic organic
compounds

i. Bridged (3 marks)

ii. Fused (3 marks)

iii. Spirocyclic (3 marks)

b. Name the following compounds using IUPAC

c. i. Differentiate between glucose and fructose in terms of their functional groups

and homologous series. (4
marks)

ii. Explain the oxidation of glucose using ammoniacal silver nitrate. (3 marks)

11. a. i. Classify amines based on R-groups) attached to nitrogen atom.

(4 marks)
 ii. Explain using equation the properties of amines, as bases.(3 marks)

iii. State any three applications of amines. (3 marks)

b. Describe the mechanism for monobromination of methane in presence of sunlight.

(6 marks)

c. Explain the following terms

i. Peroxide effect. (2 marks)

ii. Oxidative cleavage. (2 marks)

iii. Inductive effect. (2 marks)