Download Experiment 1 Structural Organic Chemistry This exercise will allow

Experiment 1
Structural Organic Chemistry
This exercise will allow you to familiarize yourself with the 3-dimensional (3-D)
structures of some hydrocarbons and to reinforce the nomenclature for alkanes and some of their
derivatives. When evaluating the 3-D aspect of your models you should be thinking of geometry
and its associated bond angles. From the lecture and your textbook readings you should know the
terms associated for a carbon atom that has four groups covalently bonded to it such that the
attached atoms are equally spaced and have equal bond angles. Additionally, this exercise will
allow you to expose you to the topics of isomers, structural formula, condensed structural
formula, and skeletal formulas.
Work in groups of three (or two if someone is missing from your bench). You will be
using the model kits at your bench. The important pieces are:
1)
the black balls with four holes that represent carbon,
2)
the green ball to represent chlorine,
3)
the red ball to represent oxygen,
4)
and the sticks to represent bonds to connect the carbon atoms to one another and to
connect the carbon atoms to hydrogen atoms.
Typically, the small grey balls with one hole represent the hydrogen atoms, but to
conserve time, and the number of pieces in your model kit, a stick (bond) attached to a
carbon atom and not connected to anything else will represent the C-H bonding arrangement.
As you construct each molecule discuss it within your group and make sure that each
member of the group understands all aspects of it before moving on to construct the next
model. If there are doubts about a particular model be sure to consult with your instructor.
Experiment 1 Report Sheet
Name ____________________________________
I. Build a model of methane, CH4
1. What is the geometry associated with this structure? _______________________
2. What is the value of the H—C--H bond angles? _____________________
II. Build a model of chloromethane (methyl chloride), CH3Cl
1. Draw a wedge
and hash mark
geometry about the atom:
picture of CH3Cl that best illustrates the
2. Is the geometry the same as methane? __________
3. Are the hydrogen atoms equivalent (i.e., do they have identical environments with respect to
the other atoms adjacent to themselves)?
III. Build a model of CH2Cl(OH)
1. Is the geometry the same as the previous two structures? __________
2. Are the hydrogen atoms attached to the carbon atom equivalent? __________
IV. Build a model of C2H6
1. Draw a structural formula of C2H6
2. Draw a condensed structural formula of C2H6
3. Are the two carbon atoms of C2H6 equivalent? __________
4. Are the six hydrogen atoms of C2H6 equivalent? __________
5. What is the IUPAC name for this compound? ___________________
V. Build a model for CH3CH2Cl
1. Are the carbon atoms in CH3CH2Cl equivalent? _________
2. Are the hydrogen atoms in CH3CH2Cl equivalent? _________
3. What is the IUPAC name for this compound? _______________________
VI. Build all possible models for the dichloroethanes, C2H4Cl2
1. How many structural isomers exist for C2H4Cl2? ___________
2. Draw condensed structural formulas for each structural isomer of C2H4Cl2 and give the
IUPAC name of each.
VII.
Build all possible models for C3H8
1. What is the IUPAC name for this compound? __________________
2. Draw a structural formula for C3H8 and using squares, triangles and/or circles, indicate the
carbon atoms that are equivalent to each other.
3. Are the eight hydrogen atoms of C3H8 equivalent? _______
4. Is there a relationship between equivalent carbons and equivalent hydrogens? If so, state
the relationship.
VIII.
Build all possible models for C3H7Cl
1. How many structural isomers exist for C3H7Cl?
2. Draw condensed structural formulas for each structural isomer of C3H7Cl and give the
IUPAC name of each.
IX.
Build all possible models for C4H10 (Hint: straight chain versus branched chain)
1. How many structural isomers exist for C4H10?
2. Draw condensed structural formulas for each structural isomer of C4H10 and give the
IUPAC name of each. Also, using squares, triangles and/or circles, indicate the carbon
atoms that are equivalent to each other
X.
Using your C4H10 models from above, remove one hydrogen atom and replace it with a
chlorine atom to make different structural isomers of C4H9Cl.
1. How many structural isomers exist for C4H9Cl? ___________
2. Draw condensed structural formulas for each structural isomer of C4H9Cl and give the
IUPAC name of each.
XI.
Draw skeletal formulas for all possible structural isomers of C4H8Cl2, which are formed by
replacing hydrogen atoms in the various isomers of C4H9Cl shown above (X.2) with a second
chlorine atom. Give the IUPAC name of each.