CHEM191 tutorial 1
1. Write the chemical structures of the following compounds
a) 2,2-dimethyl-4-propyloctane
b) 4-isopropylheptane
c) 5-isobutyldecane
d) 6-(1,2-dimethylpropyl)-4-propyldecane
e) 2,3-dimethyl-5-(2-methylbutyl) decane
2. Provide the systematic name of each of the following:
Solution:
I. 2,2,5-trimethylhexane
II. 3-ethyl-2-methylhexane
III. 3-ethyl-4,5-dimethylheptane
IV. 6-ethyl-2,7-dimethylnonane
V. 2,3,4-trichlorohexane
3. Name the following molecules.
Solution:
a) 3-amino-2-methylbutanal
b) Diethyl ether
c) 3-dimethyl-2-butanone
d) 2-methyl-2-propanol
4. Which of the following alkanes has the highest boiling point and why?
Solution:
• Compound (i) as it is a linear hydrocarbon chain
• Its molecules are tightly packed with each other
• The branching of chains lead to less tighter binding of molecules resulting in lower boiling
point
5. Write down the Newman projections for staggered and the eclipsed conformations for butane
resulting from rotation about the C1-C2 bond.
6. How many constitutional isomers does hexane have? Draw the structural formulae and
condensed formulae for the constitutional isomers.
7. Identify the number of primary, secondary and tertiary carbons in the following structure.
Solution:
Primary (1°) carbons - 7
Secondary (2°) carbons - 12
Tertiary (3°) carbons - 5
8. Determine if the following structure is the E- or the Z- isomer.
Solution:
A – E-isomer
B – Z-isomer
