1.

Complete the following table

Compound
(valence electrons)

Lewis structure
and hybridization of
heteroatoms

3-D drawing

Polarity

e.g H2CNN
Diazomethane
This will be other
species.

2. Use curved arrows to draw a valid resonance structure for the following specie. Indicate which one is
more stable (likely taken form pushing electrons)

3. Add electrons to complete octets. Then assign formal charges as necessary and indicate the overall
charge of each species. Again, different species.

H
N
H

C
H

O
O

N
O

O
H3C

CH3

4. Define (limit your answer to the space provided): Which means definitions may be included, or actual
questions assuming you know their meaning will be asked.
a) structural isomers, geometric isomers, stereoisomers
c) Molecular formula
d) Pi anti-bonding (star) orbital
5. Draw structural formulas (CH3CH2 etc, or line, your preference) for two secondary amines with the
molecular formula C4H11N.
This question indicates you should know the functional groups shown in class to draw isomers of any
other functional group. (MMII) has exercises about this.
6. Build the model indicated by the instructor. Raise your hand when you have it ready (the model will be
taken from MMI below
Compound name_____________
Methane
Ethane

Model_____________

Methanol
(methyl alcohol)
Methanamine
(Methylamine)
Oxirane
(ethylene oxide)
Methoxymethane
(dimethyl ether)
Chloromethane
(methyl chloride)
Dimethylsulfide
(methylsulfanylm
ethane)
Methanethiol
(methylmercaptan
)
Ethene (ethylene)
Propene
(propylene)
1,3-pentadiene
1,4-pentadiene
Propyne
Methanal
(formaldehyde)
Methanamide
(Formamide)
Methanoic acid
(formic acid)
Methyl
methanoate
(Methyl formate)
Propanone
Benzene
Phenol
Methanoic
anhydride
(formic
anhydride)
Methanoyl
chloride
(formyl chloride)

7. Draw the orbital sketch for formaldehyde (methanal) CH2O indicate hybridizations and angles. You
will have a different compound different than formaldehyde.
8. Arrange the CC bonds of cyclopent-1-ene (any other compound) by increasing length. Label the atomic
(e.g. sp + sp3 ) and molecular (e.g ) orbitals of each.
AOs

MOs
a

_______________
2

_______________

b
c
d
e

_______________
_______________
_______________
_______________

_______________
_______________
_______________
_______________

9. Write the IUPAC and common name for the following compound ( a branched alkane)
IUPAC ______________________________________________________________________________
COMMON___________________________________________________________________________
10. Name or write the formula for each of the following compounds (IUPAC or common where
applicable, your preference)
A cis-trans cyclo
A substituded cyclo
A bicyclo

An alkynal
Or any compounds that combines
two functional groups as in the
end of ch problems.
Name and formula

Benzene or something else

Something else

11. Something else form ch 1 or 2.

From ch 2 we will cover up to section 2.4 (included)
From the lecturure notes we will cover up to the first two pages of the lecture notes given today.
Resonance and bond lengths. Conformations will be for mid term