Organic chemistry assignment

Organic Chemistry 1 Assignment
1. Draw the Lewis structures of the following condensed structures:
a. CH3CH2CH2OCH3
b. CH2=CHCHBrCH2CH(CH3)2
c. (CH3)3CCH2CH2NHCH3
d. (CH3)2CHCH2CH=CHCO2H
2. Draw the line structures for the following Lewis structures:
3. Circle the error on each line structure

4. For each of the following molecules in line structure (skeletal figures), draw the semicondensed Lewis structure, with all missing carbons and all hydrogens:
Example:

5. Identify four different functional groups in any of the following structural formulas for
known artificial sweeteners. Circle the functional group and put the name of the
functional group next to the corresponding circle:
Resonance Exercises
1. Between each pair circle the letter of the molecule that it represents in delocalization
that indicates a correct movement of electrons with an arrow.
Example:
2. Draw each contributor you chose in Exercise 1, list the atoms involved in resonance, and
draw the contributor that is generated from that electron delocalization.
Example:

3. Draw the curved electron delocalization arrow necessary to get from the left to each
one that follows, until ending up on the right (there are no curved delocalization arrows
on the latter on the right).
4.

5. Using those in Exercise 3, draw each the resonance hybrid in the spaces provided below.
6. Each contributor on the right is wrong. Explain briefly why you are not contributing to
the resonance hybrid (“Because it is unstable.” Is not an adequate answer, be more
specific in your explanation).
7. In the following structures, circle the heteroatom that has the electrons located (which
do not resonate).

8. Below is the structure of caffeine. All nitrogens are part of the conjugated system (do
resonance). Among the lone pairs of nitrogens, circle the only lone pair that is located
(does not participate in resonance).

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