Condensed Structure and Line Structure

Example 1

Determine the Lewis Structure of the following condensed structure of oleic acid, a fatty acid that is
found naturally in various animal and vegetable fats and oils.

CH3(CH2)7CH=CH(CH2)7COOH

Solution
Start by drawing the CH3. The (CH2)7 represents a repeating unit, meaning you must draw seven CH 2‘s
one after another, which are bonded to a CH which is bonded to a CH, and then another seven CH 2‘s.
The COOH represent a carboxylic acid, which means you have a C=O connected to an O-H. Always
double check your structure to ensure every carbon is making four bonds. When you do this, you will
see the two CH must be double bonded.

Test Yourself
Common organic compounds that you likely have at home are: acetone (CH 3COCH3) found in nail polish
remover, acetic acid (CH3COOH) found in vinegar, and isopropanol ((CH 3)2CHOH) found in rubbing
alcohol. Determine the Lewis Structure for each of these household chemicals.

Answer
 Example 2

Draw the line structures for these two molecules:

Solution
Each carbon atom is converted into the end of a line or the place where lines intersect. All hydrogen
atoms attached to the carbon atoms are left out of the structure (although we still need to recognize
they are there):

Test Yourself
Draw the line structures for these two molecules:

Answers
 Example 3

Identify the chemical formula of the molecule represented here:

Solution
There are eight places where lines intersect or end, meaning that there are eight carbon atoms in the
molecule. Since we know that carbon atoms tend to make four bonds, each carbon atom will have the
number of hydrogen atoms that are required for four bonds. This compound contains 16 hydrogen
atoms for a molecular formula of C8H16.

Location of the hydrogen atoms:

Test Yourself
Identify the chemical formula of the molecule represented here:

Answer
C9H20
 Example 4

Determine the Lewis Structure of the following line structure of L-ascorbic acid (vitamin C):

Solution
At each corner or intersection of lines or end of a line, add a C:

Each C makes fours bonds. If some are not visible, then add a bond to H for each bonds missing. Also
show the bond between the O’s and H’s.

Test Yourself
Determine the Lewis Structure of the following line structure of acetaminophen, the pain and fever
medicine found in Tylenol.

Answer
1. Draw the line bond structure for the following compounds:

a) (HO)3C(CH2)2N(CH2CHO)CH(CH2CH3)2

b) CH3(CH2)3CH(CH3)(CH2)2OCH2CH3

c) HOOCCH2O(CH2)2N(CH2CH3)

d) HOCCH2CH(CH3)CH2CH(CH3)(CH2)2COOCH3

e) H2NCH2[CH(CH3)]2(CH)4CO(CH2)2CH3

f) ClCH2CH(CH3)COCH2OCH2CO(CH2)2CH3

Answers
2. For the following compounds, give the chemical formula and the condensed structure:

Answers

a) C13H26O; CH3(CH2)3C(CH3)2C(CH3)2CH2COCH2

b) C8H1414O2; CHOCH2CO(CH2)4CH3

c) C5H7O4N; COOH(CH2)2(CO)2NH2

d) C12H25O2N; CH3OCO(CH2)2C(CH3)2C(CH3)2CH(CH3)NH2

e) C12H25ON; CH3(CH2)4CON(CH2CH2CH3)2

f) C8H16O3; CH3CH2CH(OCH3)(CH2)3COOH