Organic Chemistry 1 (CHEM313)—Worksheet 01
1. For each of the following compounds, draw the complete Lewis Structure and categorize each bond as
(a) non-polar covalent, (b) polar covalent, (c) ionic. If the compound is polar covalent, indicate the
direction of the dipole moment, using the symbols d+ and d-.
CH4
H3CBr H3CH2COH
H2 S
2. Draw the Lewis Structure with formal charges on the atoms that possess the formal charge of the
following:
BCl4— H3O+
SO42— CH3+
3. Convert the following condensed formulas into bond-line structures, making sure to draw in zig-zag
formation.
CH3CH2CH2CH2CH2CH2CH2CH3
FCH2CH2I
H2C=CHCH2OH
(CH3)2CHCOOH
4. Convert the following into line-bond formula, indicating all lone pairs.
H H
H
H C C H
C
H C C H
H
H H
H
C
H
H
C
C N
H
C H
N C
C
C
H
C
C
Cl
H H H H C C
H O
5. Identify the hybridization (sp, sp2, sp3) of each carbon atom in the following molecule.
6. Identify the number of s bonds, p bonds, lone pairs, and hydrogens in the following molecules.
O
N
N
N
O
N
H
N
_____ s
_____ s
_____ p
_____ p
_____ lp
_____ lp
_____ H
_____ H
7. Redraw the structure below filling in all of the carbon atoms and hydrogen atoms.
N
8. The following are the reagent, intermediate, and product in a reaction you will learn later in Organic
Chemistry.
a.
b.
c.
d.
Identify any formal charges that are missing from the structures.
Determine the hybridization of the central carbon atom of each molecule.
Draw in all lone pairs.
Redraw the structures with all hydrogen atoms.
Cl
OH 2
9. Rank the following molecules in order from highest boiling point temperature to highest boiling point
temperature.
O
OH
O
O- Na+
OH
A
OH OH OH
E
Highest
bp
B
C
O
O
F
D
G
H
Lowest
bp
10. Propan-1-ol (CH3CH2CH2OH) and methyl ethyl ether (CH3OCH2CH3) have the same molecular formulas
but different bonding (constitutional isomers). These two molecules have drastically different boiling
points: 97.5 oC for propan-1-ol and 45.32 oC for methyl ethyl ether.
Draw the Lewis structure of each molecule. Explain the difference in the boiling points of these
molecules, using intermolecular forces. (1—3 complete sentences)