1
CHEMISTRY 1A6 - 01 / 02
TUTORIAL PROBLEM SET #8 FEBRUARY 28, 1994
Term 2. Dr. R.A. Bell, Dr. M.A. Brook
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1.
Draw line structures and name 5 of the structural isomers of molecular formula C5H11Cl.
Cl
A
Cl
G
D Cl
Cl
Cl
Cl
B
H
E
Cl
C Cl
F
A) 1-chloropentane, B) 2-chloropentane, C) 3-chloropentane, D) 1-chloro-3-methylbutane, E) 2-chloro-3-methylbutane, F)
2-chloro-2-methylbutane, G) 1-chloro-2,2-dimethylpropane, H) 1-chloro-2-methylbutane,
2.
Name all the functional groups in the following molecule.
ester
alcohol
O
OCH3
HO
amine
NH2
O
ketone
O
H
alkene
aldehyde
3.
Write Lewis structures for the following:
i) CH3O2CH3 ii) HCO2CH3 iii) BrCHCH3CH2Cl
Br
O
CH3
H3C
O
Cl
O
O
4.
CH3
iv)
CH3COC 2H5 v) CH3CHNOH
H
O
N
H
CH3
O
CH2
Write out the structural formulas for the following molecules.
2
i) 2-amino-1-hydroxybutane
methylhexane
ii) cis-1-chloro-3-methylcyclopentane iii) 2-bromo-3-chloro-3Br
Cl
OH
CH3
NH2
5.
Cl
Determine the E or Z geometric configurations for the following alkenes and name them.
H H3CH2C
OCH
3
i)
E-cyclodecane
6.
CH3
H3C
Br iii)
ii)
E-2-bromobut-2-ene
Z-2-methoxy -3-methylpent-2-ene
Draw Newman projections for 1-propanol looking along the C1-C2 bond. Label each conformer as
anti or gauche. Which of these three would you expect to be the most stable.
CH3
CH3
CH3
H
H
H
OH
H
H
H
H
OH
H
H
H
H
H
gauche
anti
gauche
HO
The anti is more stable.
7.
Write out all the structural and geometric isomers (stereoisomers) of chloromethylcyclohexane. Use
planar projections formulae and indicate the orientation (stereochemistry) of the Cl and Me groups by
using a wedged line (out of the plane of the page) and dashed line (below the plane of the page).
Label each of the isomers are cis or trans.
Cl
not relevent
Cl
Cl
Cl
trans
cis
trans
Cl
Cl
Cl
cis
trans
cis