10.1 ORGANIC CHEMISTRY · RULES IN NAMING ORGANIC COMP0UNDS 1. Select the longest continuous carbon...

10.1 ORGANIC CHEMISTRYFundamentals of chemistry

INTRO TO ORGANIC

• Organic Chemistry is the field of chemistry that studies carbon-based compounds.

• Carbon has four valence electrons (can have four bonds, mostly C-H bonds)

• Carbon can undergo catenation, which is creating long chains of repeating structures (ex.

Crude oil)

• In order to understand organic chemistry you need to understand the following

concepts: chemical bonding, nomenclature, chemical structure, stoichiometric

relationships, functional groups, and reaction mechanisms

• Organic chemistry can be applied to many topics including, but not limited to,

synthetic medicines and drugs, industry and chemical kinetics.

INTRO TO ORGANIC

• The empirical formula is the simplest whole number ration of the elements present in

a compound.

• Molecular formula the total number of atoms of each element present in a molecule

of the compound. A molecular formula is the empirical formula multiplied by an

integer (the integer can be 1)

HYDROCARBONS

• Only contain carbon and hydrogen.

• Alkanes are a family of hydrocarbons.

ALKANES

• They are all straight chains and the molecular formula of all Alkanes can be found

using CnH2n+2 (non-cyclic)

• Contain only 90°angles

• Tetrahedral shape

THERE ARE DIFFERENT WAYS TO REPRESENT THE STRUCTURE

1. Write the Lewis structure to get the full structural formula

2. Write out the carbons and hydrogens as they are bonded together

3. Write the Sketch Structural Formula

4. Write the stereochemistry using dashes and wedges

Ex. Butane C4H10

#1

#2 CH3CH2CH2CH3

#3

#4

THERE ARE DIFFERENT WAYS TO REPRESENT THE STRUCTURE

#1

#2 CH3CH2CH2CH3

#3

#4

CO

PY

OR

PR

INT

TH

IS O

UT

HOMOLOGOUS SERIES

• Homologous Series are a series of compounds that have the same functional group

each member differs from the next by a common structural unit (usually –CH2–)

• Functional groups- an atom or group of atoms that give the molecules its

characteristics chemical properties. The reactive part of the molecule.

• Homologus Series have a trend physical properties like boiling point, similar

chemical properties and a similar formula

CO

PY

OR

PR

INT

TH

IS O

UT

FU

NC

TIO

NA

L G

RO

UPS

ALKENES

• All have a

C=C bond

• Follow

CnH2n (non-

cyclic)

ALCOHOLS AND AMINES

• Alchol’s mus contain –OH group. Shown below are a few examples

• Amines-there are three different amine groups in the table. These will be discussed

in more detail later in the notes.

BENZENE RINGS

• C6H6 is the molecular formula

• The molecule is planar

• Compounds with a benzene ring are called aromatic. Without a benzene ring you

can call them aliphatic.

• When something is attached to the benzene ring it will replace a hydrogen. The

formula can be written in different ways. For example C7H8 can be written as it

structural formula C6H5CH3. C6H5 is often referred to as phenyl.

BOILING POINT OF HOMOLOGOUS PAIRS

• Increasing the number of carbons will increase the boiling point for homologous

pairs.

• Changing the functional group will change the boiling points because it will change

the type of intermolecular forces

• Ranking boiling points: Alkanes (dispersion)< Esters (dipole) < Alcohols (hydrogen

bonding)

SATURATED COMPOUNDS VS. UNSTATURATED

• Saturated compounds have double or triple bonds.

• Unsaturated compounds only have single bonds

NAMING ALKANES

NAMING ALKANES (CONT)

• The following slides contain examples of each type of functional group they were

created by Lexter Supnet can be found on line at

http://www.slideshare.net/lexter1321/nomenclature-of-organic-compounds-

iupac?from_action=save

•

http://www.slideshare.net/lexter1321?utm_campaign=profiletracking&utm_medium=sssite&utm_source=ssslideview

http://www.slideshare.net/lexter1321?utm_campaign=profiletracking&utm_medium=sssite&utm_source=ssslideview

NOMENCLATURE

Early organic chemists often assigned names related to the origin or properties

of new compounds. Some of these names are still in common use. Citric acid if found in

citrus fruit; uric acid is present in urine; formic acid is found in ants (from the Latin word

for ant, formica); and morphine induces sleep (from Morpheus, the ancient Greek god

of sleep). As thousands upon thousands of new compounds were synthesized, it

became apparent that a system of common names was unworkable. Following several

interim systems, one recommended by the International Union of Pure and Applied

Chemistry (IUPAC) was adopted.

RULES IN NAMING ORGANIC COMP0UNDS1. Select the longest continuous carbon chain in the molecule, and use the hydrocarbon

name of this chain as the base name. Except for the common names methane, ethane,

propane, and butane, standard Greek prefixes relate the name to the number of C

atoms in the chain, as in pentane (C5), hexane (C6), heptane (C7), octane (C8),…

2. Consider every branch of the main chain to be substituent derived from another

hydrocarbon. For each of these substituents, change the ending of its name from ane to

yl. That is, the alkane substituent becomes alkyl group.

3. Number the C atoms of the continuous base chain so that the substituents appear at the

lowest number possible.

4. Name each substituent according to its chemical identity and the numbers of the C

atom to which it is attached. For identical substituents use di, tri, tetra, and so on, and

write the appropriate carbon number for each substituent.

5. Separate the numbers from one another by commas, and from letters by hyphens.

6. List the substituents alphabetically by name.

SOME COMMON ALKYL GROUPSNAME STRUCTURAL FORMULA

Methyl CH3

Ethyl CH2CH3

Propyla CH2CH2CH3

Isopropyl CH3CHCH3

Butyla CH2CH2CH2CH3

Isobutyl CH3

CH2CHCH3

s-butylb CH3CHCH2CH3

t-butylc CH3

CH3CCH3

aIn the past, the prefix normal or n- was used for a straight-

chain alkyl group, such as n-propyl or n-butylbs = secondaryCt = tertiary

ALKANE

Class

General

Structural

Formula Example

Name of

Example

Alkane R H CH3CH2CH2CH2CH2CH3 Hexane

*The functional group is shown in red, R stands for an alkyl group

ALKENE

Class

General

Structural

Formula Example

Name of

Example

Alkene C C CH2 CHCH2CH2CH3 1-Pentene


ALKYNE

Class

General

Structural

Formula Example

Name of

Example

Alkyne C C CH3C CCH2CH2CH2CH2CH3 2-Octyne


ALCOHOL

Class

General

Structural

Formula Example

Name of

Example

Alcohol R OH CH3CH2CH2CH2CH2OH 1-Butanol


ALKYL HALIDE

Class

General

Structural

Formula Example

Name of

Example

Alkyl halide R X** CH3CH2CH2CH2CH2CH2CH2Br 1-Bromohexane


**X stands for a halogen atom – F, Cl, Br, I

ETHER

Class

General

Structural

Formula Example

Name of

Example

Ether R O R CH3 O CH2CH2CH3 1-Methoxypropane

(methyl propyl ether)



AMINE

Class

General

Structural

Formula Example

Name of

Example

Amine R NH2 CH3CH2CH2 NH2 1-Aminopropane

(propylamine)



Exercise: Give the appropriate IUPAC name of the amine

CH3CH(NH2)CH2CH2CH3

Ans: 2-Aminopentane

ALDEHYDE

Class

General

Structural

Formula Example

Name of

Example

Aldehyde O

R C H

O

CH3CH2CH2C H

Butanal

(butyraldehyde)


KETONE

Class

General

Structural

Formula Example

Name of

Example

Ketone O

R C R

O

CH3CH2CH2CCH2CH3

3-Hexanone

(ethyl propyl ketone)


CARBOXYLIC ACID

Class

General

Structural

Formula Example

Name of

Example

Carboxylic

acid

O

R C OH

O

CH3CH2CH2C OH

Butanoic acid

(butyric acid)


ESTER

Class

General

Structural

Formula Example

Name of

Example

Ester O

R C OR

O

CH3CH2CH2C OCH3

Methyl butanoate

(methyl butyrate)


AMIDE

Class

General

Structural

Formula Example

Name of

Example

Amide O

R C NH2

O

CH3CH2CH2C NH2

Butanamide

(butyramide)


ARENE

Class

General

Structural

Formula Example

Name of

Example

Arene Ar H**

CH2CH3

Ethylbenzene


**Ar stands for aromatic (aryl) group such as the benzene ring

ARYL HALIDE

Class

General

Structural

Formula Example

Name of

Example

Aryl halide Ar X**

Br

Bromobenzene



***X stands for halogen atom – F, Cl, Br, I

PHENOL

Class

General

Structural

Formula Example

Name of

Example

Phenol Ar OH**

Cl OH

4-Chlorophenol



***X stands for halogen atom – F, Cl, Br, I

REFERENCES

• PETRUCCI, R.H., HARDWOOD, W.S., HERRING, F.G. 2002. General Chemistry:

Principles and Modern Applications. 8th Edition. Pearson Education South Asia Pte.

Ltd. Singapore.

• Collins English Dictionary – Complete & Unabridged 2012 Digital Edition

• http://science.uvu.edu/ochem/index.php

http://science.uvu.edu/ochem/index.php

10.1 ORGANIC CHEMISTRY · RULES IN NAMING ORGANIC COMP0UNDS 1. Select the longest continuous carbon...

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