St. Clare's Girls' School
Form 7 AL Chemistry
Assignment 1 - Hydrocarbons
1. (a) Give the IUPAC name for the hydrocarbon, A, with the following skeleton:
CH3
CH3CH2C
CHCH3
(b) Give, with explanation, the major product formed when A is allowed to react with
hydrogen iodide. Write a mechanism for the reaction and draw a corresponding labelled
energy profile diagram.
2. Give the structural formula of the major organic product expected from each of the
following reaction:
KMnO4
(a)
CH2
CH3CH
Na2CO3
CH2
CH3CH
(b)
NaCl
c. H2SO4
- +
3. Chloric(I) acid is polarized as HO—Cl. Give, with explanation, the major product formed
from its addition to 3-methylpent-2-ene, and suggest a mechanism for the reaction.
4. Dehydration of C gives 3 products, E, F and G all with the formula C4H8. On treatment with
ozone followed by hydrolysis, E gives methanal among other products, but F and G do not
give methanal. Give structures for E, F and G and an equation for the ozonolysis reaction
involving E.
CH3CH2CHCH3
C:
OH
5. Give the IUPAC name for the following compound:
(a) CH3 CH CH Cl
(b) Cl CH CH2Cl
Cl
(c)
CH3CCl
(d)
CH3
C
C
CHCH3
CH3
(e)
CH3CH2CH2CCH3
CH2
6. Give the structural formulae of the reactants that form but-2-ene when treated with the
following reagents.
(a) Heating with concentrated H2SO4
(b) Alcoholic KOH
(c) Hydrogen and a catalyst
7. From the following facts and observations, deduce functional group(s) and structural
information for the organic compounds B and C, giving reasons to support your deductions.
In addition, suggestion two possible structures for each compound.
(a) A hydrocarbon, B, has a relative molar mass between 100 and 110, and gives 88.89% of
carbon in elemental analysis. On catalytic hydrogenation, B absorbs 3 moles of
hydrogen. When subjected to ozonolysis, followed by treatment with zinc and water, one
CH3C
mole of B yields, 2 moles of HCHO and 2 moles of
C
O
CHO
.
(b) C has a molecular formulae C6H12 and does not decolourize bromine water.
(Relative atomic masses: H, 1.01: C, 12.00: O, 16.00)
8. Using equations, show the reactions you would employ for he following conversions in the
laboratory. Give the reagent(s) for each step and the structures of all intermediate
compounds.
(a) CH3CH2CH2Br
(b) CH3CHCH3
CH3C
CH
CH3CH
OH
O
9. An acyclic hydrocarbon G, with relative molecular mass of between 60 and 80, contains
85.6% carbon and 14.4% hydrogen by mass.
(a) Determine the molecular formula of G.
(b) Give all possible structures for the molecular formula determined in (a).
(c) G, on ozonolysis, yields H and J, both of which contain CH3CO- group. Give the
structures of G, H and J.
(d) Give the systematic name of G.