SOALAN AMAL KEBAJIKAN ALKENE SK027 2009/2010

1. The skeletal formula of an unsaturated hydrocarbon, Q is;

(i) Name Q according to the IUPAC nomenclature: ___________________ _

(ii) What type of isomerisme is exhibit by Q? __________________________

(a) Draw the structural products formed when Q reacts with

(i) Bromine in CCl4 (ii) HBr and peroxide

(b) Q can be hydrated by adding concentrated sulphuric acid, followed by hydrolysis.

Write equation for the reaction and identify the major and minor product.

(c) When Q is treated with ozone and zinc and then hydrolysed, two compound, R and S are obtained.
Draw the two compounds R and S.

2. Specify reasonable structures and give names for the following compounds based on the given
information:
i. Compound R reacts with a hot, acidified and concentrated potassium manganate(VII) solution to
yield 3-cloro-3-methylpentanoic acid, carbon dioxide and water.

ii. Compound S undergoes addition of one mole of hydrogen in the presence of platinum catalyst to
form 2,3-dimethylbutane. Ozonolysis of S gives only propanone as organic product.

iii. Compound T reacts with ozone, and subsequent treatment with zinc/H 2O to produce HCHO and
(CH3)2CHCOCH3
3. Two type of alkenes can be prepared from dehydration of alcohols:.
CH3
conc H2SO4
CH3 C CH2CH3 K + 2-methylbutene

OH (major) (minor)

i. Write the structural formula and IUPAC name of compound K.

ii. What rules those use to determine K as a major product?

iii. Minor product was then used to react with hydrogen chloride. Write the equation and indicate the
mechanism for the reaction.

4. Compound Q (C8H8) reacts with one mole equivalent of H2 gas over Pt catalyst at atmospheric
pressure to form R (C8H10).
Both Q and R are oxidized by concentrated hot KMnO4 solution to form benzoic acid. Q reacts with
Br2 in CCl4 to form S (C8H8Br2) while R only reacts with Br2 at high temperature to form T
(C8H9Br). Ozonolysis of Q yields benzaldehyd e and methanal only.
Determine the structure of Q, R, S and T and write the chemical equations for all reactions involved.