EXTRA TUTORIAL FIS 2054

CHAPTER 1 – 5

1. Compund T is shown as below:

H
CH3CH2 – C – W

Show the distribution of electrons during the bond cleavage of C – W in compound T

to form:

a. free radical
b. carbocation
c. carbanion

2. The structure of compound E is shown as below:

H H H
CH3-C=C-C-CH3

OH
a. Draw and label the cis-trans isomer of E.
b. Can E exists as a pair of enantiomers? Explain your answer.

3. The chlorination of propane under sunlight forms a mixture of compound H and I.

a. Give the structure of compound H and I.
b. Identify the major product of the reaction.
c. Write the mechanism of major product.

4. Write the equation and obeservations for each of the following reaction.
a. 5 drops if bromine in inert solvent was added to propane and the mixture was
then exposed to sunlight.
b. 3 mL of cold, dilute and alkaline potassium manganate (VII) solution was
added to 3-heptene.

5. The structure of compound I, II, III and IV are shown as below:

CH3CH2CH2CH2CH3 CH3CH2CH(CH3)CH3
I II
CH3CH2CH2CH3 CH3C(CH3)2CH3
III IV
Arrange these compounds in order of decreasing boiling point. Explain your answer.

6. Draw the structure of product formed when 1-ethylcyclopentene reacts with

a. Hydrogen chloride
b. Hot and acidified potassium manganate (VII) solution
c. Cold, dilute and alkaline potassium manganate (VII) solution
d. Ozone followed by zinc and acid.
7. 2-methylbutanoic acid exists as a pair of enantiomers.
a. By using three-dimensional formula, draw a pair of enantiomers of 2-
methylbutanoic acid.
b. Can the enantiomers rotates the plane-polarized light? Explain your answer.

8. Benzene reacts with nitric acid, HNO3 in the presence of sulphuric acid, H2SO4, by
electrophilic aromatic substitution reation. Write the mecahnism for this reaction.

9.

a. Give IUPAC name for the above compound.

b. Show how the above compound can be synthesised from benzene. State all
the reagents and intermediates formed.

10. By using chemical equations, show how 1-butanol can be prepared from 1-
bromopropane.

11. B and C are positional isomers with molecular formula of C4H9Cl. Both B and C can
react with aqueous sodium hydroxide: B forms D via SN1 mechanism while C forms E
via SN2 mechanism. The products, D and E have the same molecular formula
C4H10O.

a. Draw the structure of B, C, D and E.

b. Name the compound B according to IUPAC nomenclature.
c. Write the SN1 mechanism for the formation of D.

12.

F G
Predict which compound would be more reactive towards SN1 mechanism. Explain
your answer.

13. Show how the benzoic acid can be prepared by:

a. Benzene,
b. Chlorobenzene

14. When 2-bromo-2-methylbutane reacts with water, 2-methyl-2-butanol is produced.

Meanwhile, 2,3-dimethyl-2 butanol is produced if 3-bromo-2,2-dimethylbutane reacts
with water.
a. Write a balanced equation for the reaction of 2-bromo-methylbutane with
water.
b. Write the mechanism for the formation of 2,3-dimethyl-2-butanol from 3-
bromo-2,2-dimethylbutane.
15. Two unsaturated compounds, P and Q formed when a reagent R reacts with
compound N.

Reagent R
P+Q

a. Draw the structure P and Q.

b. Name the rule used to identify the major product.
c. Identify and explain how the major product is determined.
d. State the reagent R.

16. Suggest a chemical test to distinguish between

a. C6H5OH abd C6H11OH
b. CH3CH(OH)CH3 and (CH3)2C(OH)CH2CH3
State the reagent, obeservation and write the reaction equations invovled for each
chemical test.

17. Show the conversion of the following compounds by using suitable chemical
equation.
a. 1,2-butanediol from 1-butanol
b. Cyclopentylmethanol from bromocyclopentane
c. 1-ethylcyclopentanol from cyclopentanone

18. Deduce the structure if compound K, L and M from the following observations.
a. Alcohol K, C3H8O does not show any changes when Lucas reagent is added
but it reacts with potassium permanganate to form porpanoic acid.
b. Alcohol L, C4H10O which is an optically active molecule gives positive result
with iodine in base.
c. Alcohol M, C5H12O immediately turns cloudy when Lucas reagent is added,
but does not show any changes with acidifeid potassium dichromate (VI).

19. The structure of two hydroxyl compounds are given as below:

T U
a. State the class of compound for T and U.
b. Compare teh acidity of T and U. Explain your answer.
c. Wirte the equation for the reaction between U and FeCl3 solution. Give the
observation involved.
d. Give the sructure of the prodcut formed when T and U react with sodium
hydroxide solution.
20. Explain the following observations:
a. CH3CH2CH(OH)COOH has higher boiling point than CH3CH2COCOOH.
b. Phenol is more acidic than 1-propanol.
c. 2-mehyl-2-propanol does not react with acidified solution of KmnO4.
d. Both phenol and ethanol react with sodium metal but only phenol dissolve in
aqueos NaOH.
e. 2-pentanol gives yellow precicpitate with iodine in NaOH solution.