CHEM 357

Ashley Causton 2012 N01 The Language of Organic Chemistry

BUILDING ON:

Chemical symbols for atoms Empirical and molecular formulas Drawing and interpreting organic structures (1.9, 1.10, 1.16, 1.17) Recognizing functional groups (1.18)

OBJECTIVES:

How to Draw and Interpret Organic Structures: Need to include all the necessary information Reduce superfluous information for ease of viewing structures Drawing Hydrocarbon Frameworks: The hydrocarbon framework is made up of hydrogen and carbon atoms it can be in a straight or branched chain, or in a ring Carbon can form four covalent bonds to other atoms Hydrogen can form one covalent bond to other atoms Rules for drawing hydrocarbon frameworks (using a five carbon chain as an example): o Notice the three dimensional shape of the molecule

H H H H H H C C C C C H H H H H H

1. Draw chains of atoms as zig-zags (to imitate the three dimensional shape)

H H H H H H C C C C C H H H H H H
2. Miss out the Hs attached to carbon atoms, along with C-H bonds. Occasionally the Hs are included, especially is they take place in a reaction or are part of a functional group (see below)

3. Miss out the capital Cs representing carbon atoms

CHEM 357

Ashley Causton 2012

Draw three different hydrocarbons that contain two carbon atoms. Calculate the empirical formula for each.

Hint: Carbon can form single, double and triple bonds with itself add the appropriate number of hydrogen atoms to the carbon frameworks that you draw Work out the molecular formula of the five carbon chain molecule shown.

Hint: Check your answer by looking at the structure on the previous page Draw stick diagrams of hydrocarbon molecules with five carbon atoms (containing only single bonds) that have a: 1. Single chain 2. Branched chain 3. Ring

Re-draw (and therefore tidy up) the following as stick representations

H2 C H2 C H3C CH H2C CH2

H2C CH3 CH3 H C C H2 CH3

CHEM 357 Used to represent molecule in three dimensional space

Ashley Causton 2012

H
Represented as:

H H

Heteroatoms: Non-carbon or hydrogen atoms Most commonly O, N, F, Cl, Br, I, S, P, Si for Organic Chemistry These are ALWAYS included in the structural drawing Heteroatoms are generally the reactive portion of organic molecules How many covalent bonds can be made by the following atoms: O= S= N= F= Cl = Br = I=

Functional Groups: Functional groups are the key to the chemistry of molecules Diagrams must emphasize the functional groups, and let the hydrocarbon framework fade into the background Circle & name the functional groups in the molecule below: NutraSweet 200 times sweeter than sugar

CO2H

H 2N O

H N

O O

What is the molecular formula of this molecule ?

CHEM 357 Circle & name the functional groups in the molecule below:

Ashley Causton 2012

Astra-Zenecas Tenormin is a cardiovascular -blocker for the treatment and prevention of heart disease

OH O

H N

What is the molecular weight of Tenormin ?

Name the functional group in the molecules below:

Me CN Me NO2 H3C O CH3 H O

Functional Groups of Carbon: Carbon-carbon double and triple bonds are considered to be functional groups Name the following functional groups:

Calculate the molecular and empirical formulae of the above molecules

Suggested Problems: 1.40, 1.41, 1.42, 1.43, 1.44