Questions on Fundamentals of organic chemistry (2)
1. State the condensed structural formulas, together with their IUPAC names, for all the structural isomers of C
6
H
14.
2. Models showing the structural formulas of two compounds A and B, both with a similar molar mass
(74 and 72 g mol -1 respectively), are shown below:
(a) Identify the functional groups contained in compounds A and B.
(b) State the IUPAC names for compounds A and B.
A___________________________ B________________________________________
(c) Deduce which of the two compounds, A or B, will have the higher boiling point and which will be more soluble in water. Explain your deduction.

3. (a) State the IUPAC names of the following three alcohols:
____________________ _________________________ ____________________
(b) Classify these three alcohols in terms of primary, secondary or tertiary.
4. Identify the functional groups present in:
(a) Tyrosine and (b) Aspirin

Answers
1. CH
3
CH
2
CH
2
CH
2
CH
2
CH
3
or CH
3
(CH
2
)
4
CH
3
: hexane
CH
3
CH(CH
3
)CH
2
CH
2
CH
3
: 2-methylpentane
CH
3
CH
2
CH(CH
3
)CH
2
CH
3
: 3-methylpentane
CH
3
C(CH
3
)
2
CH
2
CH
3
: 2,2-dimethylbutane
CH
3
CH(CH
3
)CH(CH
3
)CH
3
: 2,3-dimethylbutane
2. (a) A: carboxyl B: carbonyl (or ketone)
(b) A: propanoic acid B: butan-2-one (or 2-butanone)
(Note: As there is only one isomer of butanone the name butanone is also acceptable for B.)
(c) A (propanoic acid) will have the higher boiling point as there is hydrogen bonding between the molecules which are stronger intermolecular forces than the dipole-dipole interactions in B (butan-2one). Due to hydrogen bonding A will also be more soluble in water.
3. (a) I. propan-2-ol (or 2-propanol)
II. butan-1-ol (or 1-butanol)
III. 2-methylpropan-2-ol
(b) propan-2-ol (I) is secondary butan-1-ol (II) is primary
2-methylpropan-2-ol(III) is tertiary.
4. (a) Tyrosine: amine (or amino), carboxyl, phenyl and hydroxyl.
(b) Aspirin: carboxyl, phenyl and ester.