Module 6 - Introduction to Organic Compounds

6.1 CHARACTERISTIC FEATURES OF ORGANIC COMPOUNDS 

CHARACTERISTIC FEATURES OF ORGANIC COMPOUNDS

Characteristics of Organic Compounds

Simple organic compounds that contain just one or two carbon atoms, respectively, are methane, CH 4,
and ethanol, C2H5OH.

Methane is the main component of natural gas.

Ethanol is the alcohol present in alcoholic beverages.

Two more complex organic molecules are capsaicin and caffeine.

Capsaicin is responsible for the spiciness of peppers, and is used for topical pain-relief medicines.
Caffeine is a natural stimulant most commonly found in tea, coffee, and cacao plants. It works by
stimulating the brain and central nervous system, helping you stay alert and prevent the onset of
tiredness.

 
 Common features of organic compounds:

1.       All organic compounds contain carbon atoms and most contain hydrogen atoms. Carbon
always forms four covalent bonds and hydrogen always forms one covalent bond.

2.     Carbon forms single, double, and triple bonds to other carbon atoms.

When a compound contains two or more carbon atoms, the type of bonding is determined by the
number of atoms around carbon.  Consider the three compounds drawn below:

    A C atom surrounded by four atoms form four single bonds.

      A C atom surrounded by three atoms forms one double bond.

      A C atom surrounded by two atoms generally forms one triple bond.

3.       Some compounds have chains of atoms and some compounds have rings.

  For example, three carbon atoms can bond in a row to form propane, or form a ring called
cyclopropane.
 4.       Organic compounds may also contain elements other than carbon and hydrogen. Any atom
that is not carbon or hydrogen is called a heteroatom.

      Each heteroatom forms a characteristic number of bonds, determined by its location in the
periodic table.

      The common heteroatoms (N, O, F, Cl, Br, and I) also have nonbonding, lone pairs of , so that
each atom is surrounded by eight electrons.

Except for hydrogen, the common elements in organic compounds follow one rule in bonding:

𝐍𝐮𝐦𝐛𝐞𝐫 𝐨𝐟 𝐛𝐨𝐧𝐝𝐬     +      𝐍𝐮𝐦𝐛𝐞𝐫 𝐨𝐟 𝐥𝐨𝐧𝐞 𝐩𝐚𝐢𝐫𝐬     =     𝟒

 The most common multiple bonds between carbon and a heteroatom is a carbon–oxygen double bond.
(C = O). The bonding patterns remain the same even when an atom is part of a multiple bond, as shown
with methanol and formaldehyde.

These features explain why there are so many organic compounds:    Carbon forms four strong bonds
with itself and other elements.  Carbon atoms combine together to from rings and chains.
6.2 SHAPES OF ORGANIC MOLECULES

SHAPES OF ORGANIC MOLECULES

The Valence-Shell Electron-Pair Repulsion Theory (VSEPR). 

VSEPR theory, is a model used in chemistry to predict the geometry of individual molecules from the
number of electron pairs surrounding their central atoms. The most stable arrangement keeps the
groups on a central atom as far away from each other as possible.

The table below shows the Electron Pair Geometry and Molecular Geometry.

*An atom surrounded by two groups is linear

and has a bond angle of 180o

Each carbon atom in acetylene , C2H2, is

surrounded by two atoms and no lone pairs.

Thus, each H – C – C bond angle is 180 o, making

all four atoms of acetylene linear:

*An atom surrounded by three groups is

trigonal planar and has a bond angle of  120o . 

Each carbon atom in ethylene, CH2 = CH2, is surrounded by three atoms and no lone pairs.
Thus, each H – C – C  bnd angle is 120o . and all six atoms of ethylene lie in plane.

*An atom surrounded by four groups is tetrahedral and has bond angles
of 𝟏𝟎𝟗.5o

The carbon atom in methane (CH4) is bonded to four hydrogen atoms, pointing to
the point of a tetrahedron

To draw the three-dimensional tetrahedron on a two-dimensional page, place two of the bonds in the
plane of the page, one bond in front, and one bond behind.  

A  solid line  for bonds in the plane

A  wedge  for a bond in front of the

plane

A  dashed line  for a bond behind

the plane

All carbons having four single bonds are tetrahedral.

In the molecule Ethane, C2H6, each carbon atom is tetrahedral and can be drawn with two bonds in the
plane, one in front on a wedge, and
one behind on a dashed wedge. The
figure below represents ethane

(A) space-filling model;

(B) Ball and Stick Model;

(C) 3-Dimensional Representation.

When determining the shape around these atoms we should not forget about the lone pairs of electrons
on nitrogen and oxygen. Consider the N atom in methylamine (CH3NH2) is surrounded by three atoms
and one lone pair - four groups.  To keep these four groups as far apart as possible, each of these groups
occupies the corner of a tetrahedron. The N atom of methylamine resembles the N atom of ammonia,
NH3.  The H- N – C bond angle of 112o is close to the tetrahedral angle of 109.5 o.

 Nitrogen is attached to 3 atoms and has 1 lone pair, making its shape a trigonal pyramid.
Consider methanol, CH3OH.  The O atom is surrounded by two atoms and two lone pairs – four groups.
To keep these groups as far apart as possible, each of these groups occupies the corner of a
tetrahedron. The O of methanol resembles the O of water, H 2O. The C – O -H bond angle of 109 o is close
to the tetrahedral bond angle of 109.5 o.

 Oxygen is attached to 2 atoms and has 2 lone pairs, making its shape bent.

For a more interactive learning about Molecular Geometry, click the link below:

https://phet.colorado.edu/sims/html/molecule-shapes/latest/molecule-shapes_en.html    

                                       

6.2a Self-Assessment

Practice your skills on these two interactive websites:

Purposegames:  Molecular Geometry                                  

https://www.purposegames.com/game/a932a0b26a      

https://www.sporcle.com/games/sproutcm/no_square_antiprismatic