CHEM120 - ORGANIC CHEMISTRY WORK SHEET 1
1. Answer the following questions with respect to compounds (A) and (B):
( A)
5
CH(CH
3
)
2
6
CH
3
C CCH CHCH
2
CHCH
1 2 4
2
CHCH
2
COOC(CH
3
)
3
3
OCHCH
3
CH
2
CH
3
(a) Draw the bond-line notation for the compounds.
( B)
2
O
CH
3
CH(OH)CH
1
2
CCH
3
(b) Identify the following substituents on structure 1(A):
CH
(i) an isopropyl group
(ii) a tert-butyl group
(iii) a sec butyl group
(c) Identify all the functional groups in compounds (A) and (B).
(d) Identify the hybridization of the numbered atoms in structures (A) and
(B).
2
2. Name the compounds (a) to (d) below according to the IUPAC rules.
(a) CH
3
CH
2
CH(CH
3
)CH
2
CH(CH
2
CH
3
)CH
3 (b)
(c) (d)

3. Write (i) structural formulae and (ii) draw the bond line notation for the following compounds:
(a) 2,2,4-trimethylhexane
(b) 3-ethyl-2,4,5-trimethyloctane
(c) 2-bromo-2,4,6-trimethyloctane
4. (a) Explain why 2-sec-butyloctane is an incorrect IUPAC name.
(b) (i) Write a correct IUPAC name and (ii) draw the bond-line notation for the
intended compound.
(c) Identify a primary (1
⁰
), secondary (2
⁰
), tertiary (3
⁰ )   and a quaternary (4
⁰
) carbon atom in CH
3
C(CH
3
)
2
CH
2
CH(CH
3
)CH
3
.

1. Name the following compounds using the IUPAC system. If any alcohols are present, indicate whether they are primary, secondary or tertiary.

2. Draw structures for:
(a) 4-isopropyldecane
(c) 3-heptyne
(e) 2-butanol
(g) 3-methylpentanal
(b) 2,2-dichloropropane
(d) 5,5-dimethylnonane
(f) 2-methyl-2-propanol
(h) 3-hydroxy-2-hexanone
(i) octanoic acid (j) 4-bromo-5 hydroxynonanoic acid
3. There are four structural isomers with the molecular formula C
4
H
9
Br. Draw structures for the four isomers. One of these can exist as a pair of optical isomers which one is this?
4. The substance 2-butanol displays optical isomers. Indicate the chiral carbon with a ‘*’. Draw three dimensional representations of the two enantiomers and label the isomers clearly.
5. Draw structures for the cis- and trans-isomers of 1-chloro-1-propene.

6. Determine the configuration of each of the following alkenes:
7. Draw the structure of trans-1,3-dichlorocyclobutane.
8. Explain why the cyclohexane boat conformation is much less stable than the chair conformation.
9. (a) Find the stereogenic center (chiral centre) in
i) CH
3
CH
2
CHICH
2
CH
3
iii) 3-methylcyclohexene ii) BrFCHCH
3 iv) 2,3-dibromobutane
10. (a) Which of the following compounds is chiral?
i) 1-bromo-1-phenylethane ii) 1-bromo-2-phenylethane
(b) Draw three-dimensional structures (perspective formulae) for the two enantiomers of the chiral compound in problem 10(a).
11. The figure below shows Fischer projection structures of 2,3-dichlorobutane.
Classify the following molecules of as either enantiomers, chiral, achiral or
meso forms. Locate the planes of symmetry, if any, and assign the corresponding configurations (R) or (S).
CH
3
CH
3
CH
3
CH
3
H
Cl
Cl
H
Cl
H
H
Cl
H
H
Cl
Cl
Cl
Cl
H
H
CH
3
CH
3
CH
3
CH
3