Organic Chemistry Summary

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Organic Chemistry

Part 1

Organic compound
 Contains carbon and hydrogen, and sometimes other nonmetals such as oxygen,
sulfur, nitrogen, phosphorus, or a halogen.

Organic compound that have Exceptions:


 Carbon monoxide
 Carbon dioxide
 Carbonates (e.g. Calcium carbonate)
 Carbides (calcium carbide)
 Pure carbon compound

Hydrocarbons
 an organic chemical compound that consist only carbon and hydrogen atoms.

2 types of Hydrocarbon
1. Saturated
 Alkanes
2. Unsaturated
 Alkenes
 Alkynes

Alkanes
 a type of hydrogen carbon in which the carbon atoms are connected by single
bond
 names for alkanes ends with anes (e.g. ethane, methane, propane).

IUPAC Names and Formulas of the First Ten Alkanes


Number of Molecular
carbon IUPAC Name Formula Condensed Structural Formula Line-angular Formula
atoms

n/a because it has only 1 carbon


1 Methane CH4 CH44

2 Ethane C2H6 CH3 - CH3

3 Propane C3H8 CH3 - CH2 - CH3

4 Butane C4H10 CH3 - CH2 - CH2 - CH3

5 Pentane C5H12 CH3 - CH2 - CH2 - CH2 - CH3

6 Hexane C6H14 CH3 - CH2 - CH2 - CH2 - CH2 - CH3

7 Heptane C7H16 CH3 - CH2 - CH2 - CH2 - CH2 - CH2 - CH3

8 Octane C8H18 CH3 - CH2 - CH2 - CH2 - CH2 - CH2 - CH2 - CH3

9 Nonane C9H20 CH3 - CH2 - CH2 - CH2 - CH2 - CH2 - CH2 - CH2 - CH3

10 Decane C10H22 CH3 - CH2 - CH2 - CH2 - CH2 - CH2 - CH2 - CH2 - CH2 - CH3

Condensed Structural Formula


 Carbon atoms and its attached hydrogen atoms are written as a group.
 Subscripts indicates the number of hydrogen atoms bonded to each.
Line-angle Formula
 A zigzag line which carbon atoms are represented as the ends of each line and
as a corner
 Arranged in zigzag when an organic molecule consists of a chain of three or
more carbon atoms.

Example: Pentane (C5H12)

H H H H H

H C C C C C H Expanded Structural Formula

H H H H H

CH3 – CH2 – CH2 – CH2 – CH3 Condensed Structural Formula

Line-angle Formula

Substituents in Alkanes

Alkyl Group
 An alkane that is missing one hydrogen atom
 Named by replacing the ane ending of the corresponding alkane yl

Writing IUPAC names for Alkanes with Substituents

Write the IUPAC name for the following alkane:

SOLUTION GUIDE
Given: six-carbon chain, two methyl groups, one bromo group
Need: IUPAC name
Connect: position of substituents on the carbon chain

Cycloalkanes
 Hydrocarbons in a cyclic or ring structure.
 Have two fewer hydrogen atoms than the corresponding alkanes
 Named by adding the prefix cyclo to the name of the alkane with the same
number of the carbon atoms.

Formula for Some Common Cycloalkanes


Alkenes and Alkynes

Alkenes
 Contain one or more carbon-carbon double bonds that form when an adjacent
carbon atoms share two pairs of valence electrons.

Alkyne
 A triple bonds form when two carbon atoms share three pairs of valence
electron.

Naming Alkenes and Alkynes

The IUPAC names for alkenes and alkynes are similar to those of alkanes. Using the
alkane name with the same number of carbon atoms, the ane ending is replaced with
ene for an alkene and yne for an alkyne. Cyclic alkenes are named as cycloalkenes.

Comparison of Names for Alkanes, Alkenes, and Alkynes

SOLUTION GUIDE
Given: five-carbon chain, double bond, methyl group
Need: IUPAC name
Connect: replace the ane of the alkane name with ene
Naming Cycloalkenes

Some alkenes called cycloalkenes have a double bond within a ring structure. If there is
no substituent, the double bond does not need a number. If there is a substituent,
the carbons in the double bond are numbered as 1 and 2, and the ring is numbered in
the direction that will give the lower number to the substituent.

Cis-trans Isomers
 The atoms or group are attached to the carbon atoms in the double bond on
one side or another, which gives two different structures.
Cis Isomer – same side of the double bond
Trans Isomer – opposite sides

Addition Reaction for Alkenes

Summary of Addition Reaction


Hydrogenation
 In a reaction called hydrogenation, H atoms add to each of the carbon atoms
in a double bond of an alkene. During hydrogenation, the double bonds are
converted to single bonds in alkanes. A catalyst such as finely divided
platinum (Pt), nickel (Ni), or palladium (Pd) is used to speed up the reaction.
The general equation for hydrogenation can be written as follows:

Hydration
 In hydration, an alkene reacts with water (H ¬ OH). A hydrogen atom (H ¬ )
from water forms a bond with one carbon atom in the double bond, and the
oxygen atom in ¬OH forms a bond with the other carbon. The reaction is
catalyzed by a strong acid such as H 2SO4, written as H+. Hydration is used to
prepare alcohols, which have the hydroxyl ( ¬ OH) functional group. When
water (H ¬ OH) adds to a symmetrical alkene, such as ethene, a single
product is formed.

However, when H2O adds to a double bond in an asymmetrical alkene, two products
are possible. We can write the prevalent product by attaching the H - from H 2O to the
carbon that has the greater number of H atoms and the - OH from H 2O to the other
carbon atom from the double bond. In the following example, the H - from H2O attaches
to the end carbon of the double bond, which has more hydrogen atoms, and the -OH
adds to the middle carbon atom:
Aromatic Compound
 Another hydrocarbon is called benzene, because it consists of C and H. it is a
ring of six carbon atoms with one hydrogen atom attached to each carbon.
They have fragrant odors, hence the name aromatic compound.

Naming Aromatic Compound

When benzene has only one substituent, the ring is not numbered. When there are two
or more substituents, the benzene ring is numbered to give the lowest numbers to the
substituents.

When aniline, phenol, or toluene has substituents, the carbon atom attached to the
amine, hydroxyl, or methyl group is numbered as carbon 1 and the substituents are
named alphabetically.

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