Names: ____________________________
Chem 121/Dr. Rusay
Organic Chemistry
Structures, Functions and Nomenclature
1.
What is the difference between a structural formula and molecular formula? Give an example
for butane.
2.
What are structural isomers? Draw two examples using Lewis structures for C3H7Br.
3.
Name three different types of hybridized carbon atoms found in organic molecules? Draw a
Lewis structure for a molecule that represents each type.
4.
How many different substitutions can an sp3 carbon atom have? Draw examples of each.
5.
Name the first ten alkanes.
6.
What are the names of each of the alkyl groups containing from one to three carbons? Draw
Lewis structures representing each of them attached to a bromine atom. Name each of them.
7.
Consider the following line structure of a compound.
a. What is the molecular formula of this compound?
b. How many types of carbon atoms does this compound have?
(1o (3H), 2 o (2H), 3 o (1H), [4 o noH]) Identify each type of carbon and label it on the
structure provided.
8. Classify the following pairs of compounds as being either structural isomers, or identical
compounds or neither.
a)
CH3 CH CH2 CH2 CH CH3
CH3
CH3
e)
CH3
(CH3 )2CH(CH2 )2CH(CH3 )2
b)
CH 3
CH3
CH 3
CH 3
f)
CH 3
CH 3
CH 3
c)
g)
CH 2 CH 3
d)
CH3
CH3
CH2 CH2 CH CH2 CH3
h)
CH3
9.
What are geometric isomers of sp2 hybridized carbon-carbon bonds? Give examples of each
type.
10. Draw the structures (including geometric isomers) of all the alkenes with the molecular formula
C2H2Cl2. Give the IUPAC name for each compound you draw.
11. What is a functional group? Name and draw a structure for six common functional groups; at
least one should have a nitrogen atom present. (Note: Alkanes are not considered as having a
functional group. Use R- to represent a generic carbon backbone)?
12. Taxol, isolated from the bark of the Pacific Yew tree, is an anticancer drug used in the treatment
of ovarian cancer. Circle and name the functional groups present in taxol.
13. Are the functional groups in the following two molecules the same? Name each function.
O
a) CH 3 CH 2 CH 2 C OCH 2 CH 3
b)
O
CH 3 CH 2 C CH 2 OCH 2 CH 3
14. Draw structures of molecules with the formula C4H8O which contain:
a. an alcohol
b. an ether
c. a ketone
d. an aldehyde
15. Draw structures for the following compounds.
a. 2,4-dichlorobenzene
b. 1-bromo-trans-2-butene
c. 2-methyl-4-ethylhexane
d. 2-methyl-3-ethylcyclohexane
e. 2,6-dichloro-4-ethylheptane
16. As Van’t Hoff established about one hundred years ago, chiral carbons are sp3 hydridized and
have a tetrahedral shape with four different substituents bonded to the carbon. The number of
possible optical isomers equals 2n, where n = the total number of chiral carbon atoms. Circle
the chiral carbons in taxol and calculate the possible number of optical isomers.
17. Classify the following pairs of compounds as being either enantiomers, or identical compounds,
or diastereomers.
Br
a.
C
H
CH3
Cl
H
b. H C
3
Cl
Cl
C
Br
H
H3C
H3C
CH3
H
CH3
c.
OH
H
H
Br
H
H3C
H
H
Cl
Br
CH3
H
OH