Organic Nomenclature 2010

Organic Compounds
Organic Compounds
form the chemical basis of life
Nomenclature more abundant than inorganic compounds
Organic compounds Inorganic compounds
Of obtained from plants and animals

composed mainly of carbon and limited
number of other elements
derived from minerals
compositions are quite varied and include
most of the elements
most contain more atoms and have contain relatively few atoms and have
more complex structures simpler structure
Organic Compounds covalently bonded

nearly all are insoluble in water
are non-electrolyte
ionic bonded
many are soluble in water
are electrolytes
have low melting point and boiling point have high melting point and boiling point
armsalcedo2008 armsalcedo2008
O R G A N I C C H E M I S T R Y O R G A N I C C H E M I S T R Y
Organic Compounds
Organic Compounds Representation of
Representation of Compounds
Compounds
Molecular formula
Hydrocarbon exact ratio of the atoms in a molecule is given
C6H12O6 C10H22
Aliphatic Aromatic
Structural formula
shows the arrangement of atoms and bonds in a molecule
Alkanes Alkenes Alkynes Cyclic

group
Representation of
Representation of Compounds
Compounds Counting in
Counting in Organic
Organic Chemistry
Chemistry
Condensed structural formula
shows only specific bonds, other bonds are left out but implied
O • 01 = meth- • 06 = hex-
CH3CHCH2C OH • 02 = eth- • 07 = hept-
CH3
• 03 = prop- • 08 = oct-
Bond-line formula
C are represented as point or corners • 04 = but- • 09 = non-
C-H bonds are left out but implied
• 05 = pent- • 10 = dec-
Alkanes
Alkanes Alkanes
Alkanes
Simplest type of organic compound Structural Condensed Bond-line
Saturated hydrocarbons Name structural
formula structure
General formula: CnH2n+2 formula
H
Name # of C MF
Methane H C H
Methane 1 CH4
Ethane 2 C 2H6
H
Propane 3 C 3H8
Butane 4 C4H10
Pentane 5 C5H12
Hexane 6 C6H14
Ethane
Heptane 7 C7H16
Octane 8 C8H18
Nonane 9 C9H20
Decane 10 C10H22
Alkanes
Alkanes Alkanes
Alkanes
Structural Condensed Bond-line Structural Condensed Bond-line
Name structural Name structural
formula structure formula structure
formula formula
Propane Pentane
Butane Hexane
Structural Isomers
Structural Isomers Nomenclature
Nomenclature
molecules that have the same molecular formula but different structures
The General Format
PREFIX PARENT SUFFIX

C4H10 C4H10
Substituents Longest -name ending

continuous
NOTE: name
C-chain
primary (1°) carbon- C directly bonded to only one other C Halogens
secondary (2°) carbon- C directly bonded to two other C -F, -Cl, -Br, -I
Alkyl groups
tertiary (3°) carbon- C directly bonded to three other C
location
Alkyl Groups
Alkyl Groups IUPAC rules
IUPAC rules
derived from simple alkanes that has lost 1 H atom
1. Determine longest continuous chain (i.e. parent hydrocarbon)
Methane Methyl Ethane Ethyl
IUPAC rules
IUPAC rules IUPAC rules
IUPAC rules
2. Cite the name of substituent before the name of the parent 3. Number in the direction that gives the lower number for the
hydrocarbon along with the number of the carbon to which it is lowest-numbered substituent. Substituents are listed in
attached. alphabetical order – neglecting prefixes such as di- tri- tert-
etc.
2
2
IUPAC rules
IUPAC rules IUPAC rules
IUPAC rules
5. If same substituent numbers are obtained in either direction,
4. When both directions yield the same lower number for the number in direction giving lowest number to the first named
lowest numbered substituent, select the direction that yields substituent.
the lower number for the next lowest numbered substituent. 6. If compound has two or more chains of the same length,
parent hydrocarbon is chain with greatest number of
substituents.
Cycloalkanes
Cycloalkanes Nomenclature of
Nomenclature of Cycloalkanes
Cycloalkanes
alkanes in ring structures
usually drawn using bond–line structure 1. Ring is the parent hydrocarbon unless the alkyl substituent has
more carbons; in that case the substituent becomes the parent
hydrocarbon.
If only one substituent, no need to give it a number.
Nomenclature of
Cycloalkanes Nomenclature of
Cycloalkanes
2. If the ring has 2 substituents, list in alphabetical order and give 3. If there is more than one substituent, list in alphabetical order;
number 1 to first named group one substituent is given the position number 1; number either
clockwise or counterclockwise - lowest numbers
Exercises
Exercises Answers to
Answers to Exercises
Exercises
A
B
C
A D
E
C
D E
Exercises
Exercises Answers to
Answers to Exercises
Exercises
A B C
C
D E
Alkenes &
Alkenes & Alkynes
Alkynes Alkenes &
Alkenes & Alkynes
Alkynes
Unsaturated hydrocarbon
Presence of double bond (alkene) and triple bond (alkyne)
General formula: alkene = CnH2n ; alkyne = CnH2n-2
1-propene 1-butene 2-butene
Name ends with –ene (alkene) ; -yne (alkyne)
# of C Alkene MF Alkyne MF
2 Ethene C 2H4 Ethyne C 2H2 1-pentene 2-pentene
3 Propene C 3H6 Propyne C 3H4
4 Butene C 4H8 Butyne C 4H6
5 Pentene C5H10 Pentyne C 5H8
6 Hexene C6H12 Hexyne C6H10
=
7 Heptene C7H14 Heptyne C7H12 1-propyne
8 Octene C8H16 Octyne C8H14
9 Nonene C9H18 Nonyne C9H16
10 Decene C10H20 Decyne C10H18
1-butyne 2-butyne
Alkenes &
Alkenes & Alkynes
Alkynes Alkyl Halide
Alkyl Halide
common name: name of alkyl group + name of halogen, end with -ide
methyl chloride ethyl fluoride
isopropyl iodide sec-butyl bromide
IUPAC name: treat the halogen as a substituent
Alkyl Halide
Alkyl Halide Aromatics
Aromatics
refer to benzene and its structural derivatives
Benzene
a cyclic conjugated molecule
planar and has a shape of a regular hexagon
3-ethyl-1-methyl-1-cyclopentene all C are sp2-hybridized
Aromatics
Aromatics Aromatics
Aromatics
Monosubstituted Disubstituted
ethylbenzene
1,2- 1,3- 1,4-

Common name of monosubstituted benzene ring
o- m- p-
(ortho-) (meta-) (para-)
Functional Groups
Functional Groups Alcohols
Alcohols
hydrocarbon derivatives General Formula: R-OH
structural features that classify compounds by reactivity Nomenclature
causes characteristic chemical behavior common: Name of parent alkyl, followed by alcohol
determines physical properties IUPAC: Name of parent as alkane, replace –e with -ol
basis for naming organic compounds
Alcohols
Alcohols Alcohols
Alcohols
Classification
OH
1° 2° 3°
1° alcohol 2° alcohol 3° alcohol
Ethers
Ethers Aldehydes
Aldehydes
General Formula: R-O-R’ General Formula:
Nomenclature
common: Name of 2 alkyl groups in alphabetical order, Nomenclature
followed by ether IUPAC: Name of parent as alkane, replace –e with -al
IUPAC: Name of shorter R group as alkyl, replace –yl
with –oxy then name of the longer R as alkane
Ketone
Ketone Carboxylic Acid
Carboxylic Acid
General Formula: General Formula:
Nomenclature Nomenclature
IUPAC: Name of parent as alkane, replace –e with -one IUPAC: Name of parent as alkane, replace –e with –oic
+ acid
C
H OH
methanoic acid
formic acid
Esters
Esters Acid Halide
Acid Halide
General Formula: General Formula:
, where X is a halogen (F, Cl, Br, I)
Nomenclature Nomenclature
IUPAC: Name of alkyl’, name of parent alkane replace – IUPAC: Name of parent alkane replace –e with –oyl
e with –oate + name of halogen as halide
O O
C C
Br Cl
ethanoyl bromide propanoyl chloride
acetyl bromide propionyl chloride
Acid Anhydride
Acid Anhydride Organic Nitrogen
Organic Nitrogen Compounds
Compounds
General Formula:
Amine
Nomenclature General Formula:
IUPAC: Name of parent alkane replace –e with –oic
+ anhydride
O O
Nomenclature: name ending is -amine

C C
O
ethanoic methanoic anhydride
acetic propionic anhydride
NH2
ethanamine
Organic Nitrogen
Compounds Organic Nitrogen
Compounds
Amide Nitrile
General Formula: General Formula: or
O
R'
C
Nomenclature: name ending is –nitrile (or cyanide)
R N
R"
tertiary (3°) amide
Nomenclature: name ending is -amide
O N
N 3-methylpentanenitrile
N ,N-dimethylpropanamide
Organic Sulfur
Organic Sulfur Compounds
Compounds Summary
Summary
Thiol
Functional group General formula Suffix Example
General Formula:
Nomenclature: name ending is –thiol

Organic Nomenclature 2010

Uploaded by

Document Information

Original Description:

Copyright

Available Formats

Share this document

Share or Embed Document

Sharing Options

Did you find this document useful?

Is this content inappropriate?

Copyright:

Available Formats

Organic Nomenclature 2010

Uploaded by

Copyright:

Available Formats

Organic Compounds

Nomenclature more abundant than inorganic compounds

Organic compounds Inorganic compounds

Of obtained from plants and animals

Organic Compounds covalently bonded

Hydrocarbon exact ratio of the atoms in a molecule is given

Alkanes Alkenes Alkynes Cyclic

CH3CHCH2C OH • 02 = eth- • 07 = hept-

The General Format

PREFIX PARENT SUFFIX

Substituents Longest -name ending

1. Determine longest continuous chain (i.e. parent hydrocarbon)

Methane Methyl Ethane Ethyl

methyl chloride ethyl fluoride

isopropyl iodide sec-butyl bromide

IUPAC name: treat the halogen as a substituent

1,2- 1,3- 1,4-

1° alcohol 2° alcohol 3° alcohol

Nomenclature: name ending is -amine

Nomenclature: name ending is –thiol

You might also like