1. 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. 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:

3. 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=CH 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

4. 6. CH3CH2—OH CH2 ═ CH2 + H2O ethanol ethene CH2 — CH2 | | H OH Answer:
Note: Dehydration of alcohol
6. CH3CH2—OH
Al2O3
CH2 ═ CH H2O
ethanol
ethene
CH2 — CH2
| |
H OH
H2O molecule formed, the remaining bond will joined up forming a double bond
Answer:
cyclobutanol

5. 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

6. 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:

7. 10. CH3CH2CH2CH2CH2–OH + CH3CH2COOH  ? + ?
Note: Esterification
CH3CH2CH2CH2CH2–OH CH3CH2COOH  ? + ?
Pentanol
Propanoic acid
Answer: O ║
CH3CH2C–O–CH2CH2CH2CH2CH H2O
Pentyl propanoate
CH3–OH C6H5COOH  ? + ?