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 (b)

CH3CH

CH2

NaCl c. H2SO4

- + 3. Chloric(I) acid is polarized as HOCl. 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) (d)

CH3CCl
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 C O CHO

mole of B yields, 2 moles of HCHO and 2 moles of

(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 O

OH

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.