ORGANIC EXERCISE QUESTIONS. 1. Methylcyclobutane reacts with bromine under certain conditions. Draw the structural formula of all the monosubstituted methylcyclobutane produced from the reaction. Note: Methylcyclobutane is an alkane (saturated hydrocarbon), it will undergo substitution reaction where one Br atom will be substituting one H atom. Answer:
2. Draw the structural formula of all compounds produced when propane reacts with chlorine. CH3-CH2-CH3 + Cl2 ? How many possible position for substitution? Answer:
CH3-CH-CH=CH2 + H2 | CH3 CH3-CH-CH—CH2 | | | H3C H H 3-methylbutene | | | H3C H H 3-methylbutene 2-methylbutane Note: the reactant is an alkene (presence of double bond indicates an unsaturated compound), the reaction will be ‘addition reaction’. 4. CH2=CH2 + Br2 CH2—CH2 | | Br Br ethene dibromoethane Note: although benzene contains double bonds, it does not undergo addition reaction due to stability of the ring. bromobenzene
6. CH3CH2—OH CH2 ═ CH2 + H2O ethanol ethene CH2 — CH2 | | H OH Answer: Note: Dehydration of alcohol 6. CH3CH2—OH Al2O3 CH2 ═ CH2 + H2O ethanol ethene CH2 — CH2 | | H OH H2O molecule formed, the remaining bond will joined up forming a double bond Answer: cyclobutanol
8. CH3CH2CH2CH2CH2—OH + 2[O] ? + H2O Note: Oxidation of alcohol 8. CH3CH2CH2CH2CH2—OH + 2[O] ? + H2O pentanol Note: 2 H atom will combine with O from the oxidation agent to form H2O. An O atom will be attached to the C atom. Answer: Pentanoic acid
CH3CH2CH2CH2C=O + 2[H] ? | H Pentanal (aldehyde) H H Answer: Note: O atom combines with one of the H atom from reducing agent Double bond is broken, forming a new covalent bond with another H atom from reducing agent H H Pentanol Answer:
10. CH3CH2CH2CH2CH2–OH + CH3CH2COOH ? + ? Note: Esterification 10. CH3CH2CH2CH2CH2–OH + CH3CH2COOH ? + ? Pentanol Propanoic acid Answer: O ║ CH3CH2C–O–CH2CH2CH2CH2CH3 + H2O Pentyl propanoate 11. CH3–OH + C6H5COOH ? + ?