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Nomenclature

Of

Organic Compounds
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Organic Compounds
form the chemical basis of life
more abundant than inorganic compounds

Organic compounds

Inorganic compounds

obtained from plants and animals

derived from minerals

composed mainly of carbon and limited
number of other elements

compositions are quite varied and include
most of the elements

most contain more atoms and have
more complex structures

contain relatively few atoms and have
simpler structure

covalently bonded

ionic bonded

nearly all are insoluble in water

many are soluble in water

are non-electrolyte

are electrolytes

have low melting point and boiling point

have high melting point and boiling point

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Organic Compounds
Hydrocarbon

Aliphatic

Alkanes

Aromatic

Cyclic
group

Alkynes

Alkenes

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Representation of Compounds
Molecular formula
exact ratio of the atoms in a molecule is given

C6H12O6

C10H22

Structural formula
shows the arrangement of atoms and bonds in a molecule

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Representation of Compounds
Condensed structural formula
shows only specific bonds, other bonds are left out but implied

Bond-line formula
C are represented as point or corners
C-H bonds are left out but implied

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Counting in Organic Chemistry • 01 = meth- • 06 = hex- • 02 = eth- • 07 = hept- • 03 = prop- • 08 = oct- • 04 = but- • 09 = non- • 05 = pent- • 10 = dec- MSAESMALLA -GO FOR EXCELLENCEarmsalcedo2008 O R G A N I C C H E M I S T R Y .

Alkanes Simplest type of organic compound Saturated hydrocarbons General formula: CnH2n+2 Name # of C MF Methane Ethane Propane Butane Pentane Hexane Heptane Octane Nonane Decane 1 2 3 4 5 6 7 8 9 10 CH4 C 2 H6 C 3 H8 C4H10 C5H12 C6H14 C7H16 C8H18 C9H20 C10H22 MSAESMALLA -GO FOR EXCELLENCEarmsalcedo2008 O R G A N I C C H E M I S T R Y .

Alkanes Condensed structural formula Structural formula Name Bond-line structure Methane Ethane MSAESMALLA -GO FOR EXCELLENCEarmsalcedo2008 O R G A N I C C H E M I S T R Y .

Alkanes Condensed structural formula Structural formula Name Bond-line structure Propane Butane MSAESMALLA -GO FOR EXCELLENCEarmsalcedo2008 O R G A N I C C H E M I S T R Y .

Alkanes Condensed structural formula Structural formula Name Bond-line structure Pentane Hexane MSAESMALLA -GO FOR EXCELLENCEarmsalcedo2008 O R G A N I C C H E M I S T R Y .

C directly bonded to three other C MSAESMALLA -GO FOR EXCELLENCEarmsalcedo2008 O R G A N I C C H E M I S T R Y .C directly bonded to two other C tertiary (3°) carbon.Structural Isomers molecules that have the same molecular formula but different structures C4H10 C4H10 NOTE: primary (1°) carbon.C directly bonded to only one other C secondary (2°) carbon.

-Cl. -I   SUFFIX Alkyl groups location MSAESMALLA -GO FOR EXCELLENCEarmsalcedo2008 O R G A N I C C H E M I S T R Y .Nomenclature The General Format PREFIX PARENT Substituents Longest continuous C-chain name  -name ending Halogens -F. -Br.

Alkyl Groups derived from simple alkanes that has lost 1 H atom Methane Ethane Methyl Ethyl MSAESMALLA -GO FOR EXCELLENCEarmsalcedo2008 O R G A N I C C H E M I S T R Y .

Determine longest continuous chain (i. parent hydrocarbon) 2 MSAESMALLA -GO FOR EXCELLENCEarmsalcedo2008 O R G A N I C C H E M I S T R Y .e.IUPAC rules 1.

Cite the name of substituent before the name of the parent hydrocarbon along with the number of the carbon to which it is attached.IUPAC rules 2. 2 MSAESMALLA -GO FOR EXCELLENCEarmsalcedo2008 O R G A N I C C H E M I S T R Y .

Number in the direction that gives the lower number for the lowest-numbered substituent. 2 MSAESMALLA -GO FOR EXCELLENCEarmsalcedo2008 O R G A N I C C H E M I S T R Y .tertetc. Substituents are listed in alphabetical order – neglecting prefixes such as di.IUPAC rules 3.tri.

MSAESMALLA -GO FOR EXCELLENCEarmsalcedo2008 O R G A N I C C H E M I S T R Y .IUPAC rules 4. When both directions yield the same lower number for the lowest numbered substituent. select the direction that yields the lower number for the next lowest numbered substituent.

IUPAC rules 5. 6. If same substituent numbers are obtained in either direction. MSAESMALLA -GO FOR EXCELLENCEarmsalcedo2008 O R G A N I C C H E M I S T R Y . number in direction giving lowest number to the first named substituent. If compound has two or more chains of the same length. parent hydrocarbon is chain with greatest number of substituents.

This number together with the substituent name is placed inside parentheses. Numbering of the substituent begins with the carbon attached to the parent hydrocarbon. MSAESMALLA -GO FOR EXCELLENCEarmsalcedo2008 O R G A N I C C H E M I S T R Y .IUPAC rules 7.Names such as sec-butyl and tert-butyl are acceptable. but systematic substituent names are preferable.

Cycloalkanes alkanes in ring structures usually drawn using bond–line structure MSAESMALLA -GO FOR EXCELLENCEarmsalcedo2008 O R G A N I C C H E M I S T R Y .

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.Nomenclature of Cycloalkanes 1. no need to give it a number. MSAESMALLA -GO FOR EXCELLENCEarmsalcedo2008 O R G A N I C C H E M I S T R Y .

If the ring has 2 substituents.Nomenclature of Cycloalkanes 2. list in alphabetical order and give number 1 to first named group MSAESMALLA -GO FOR EXCELLENCEarmsalcedo2008 O R G A N I C C H E M I S T R Y .

If there is more than one substituent. number either clockwise or counterclockwise .lowest numbers MSAESMALLA -GO FOR EXCELLENCEarmsalcedo2008 O R G A N I C C H E M I S T R Y .Nomenclature of Cycloalkanes 3. list in alphabetical order. one substituent is given the position number 1.

Exercises A C B E D MSAESMALLA -GO FOR EXCELLENCEarmsalcedo2008 O R G A N I C C H E M I S T R Y .

Answers to Exercises A B C D E MSAESMALLA -GO FOR EXCELLENCEarmsalcedo2008 O R G A N I C C H E M I S T R Y .

Exercises A B C D E MSAESMALLA -GO FOR EXCELLENCEarmsalcedo2008 O R G A N I C C H E M I S T R Y .

Answers to Exercises A B C D E MSAESMALLA -GO FOR EXCELLENCEarmsalcedo2008 O R G A N I C C H E M I S T R Y .

alkyne = CnH2n-2 Name ends with –ene (alkene) . -yne (alkyne) # of C Alkene MF Alkyne MF 2 3 4 5 6 7 8 9 10 Ethene Propene Butene Pentene Hexene Heptene Octene Nonene Decene C 2 H4 C 3 H6 C 4 H8 C5H10 C6H12 C7H14 C8H16 C9H18 C10H20 Ethyne Propyne Butyne Pentyne Hexyne Heptyne Octyne Nonyne Decyne C 2 H2 C 3 H4 C 4 H6 C 5 H8 C6H10 C7H12 C8H14 C9H16 C10H18 MSAESMALLA -GO FOR EXCELLENCEarmsalcedo2008 O R G A N I C C H E M I S T R Y .Alkenes & Alkynes Unsaturated hydrocarbon Presence of double bond (alkene) and triple bond (alkyne) General formula: alkene = CnH2n .

Alkenes & Alkynes 1-propene 1-butene 2-butene 1-pentene 2-pentene = 1-propyne 2-butyne 1-butyne MSAESMALLA -GO FOR EXCELLENCEarmsalcedo2008 O R G A N I C C H E M I S T R Y .

Alkenes & Alkynes MSAESMALLA -GO FOR EXCELLENCEarmsalcedo2008 O R G A N I C C H E M I S T R Y .

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 MSAESMALLA -GO FOR EXCELLENCEarmsalcedo2008 O R G A N I C C H E M I S T R Y .

Alkyl Halide MSAESMALLA -GO FOR EXCELLENCEarmsalcedo2008 O R G A N I C C H E M I S T R Y .

Aromatics refer to benzene and its structural derivatives Benzene a cyclic conjugated molecule planar and has a shape of a regular hexagon all C are sp2-hybridized MSAESMALLA -GO FOR EXCELLENCEarmsalcedo2008 O R G A N I C C H E M I S T R Y .

Aromatics Monosubstituted Common name of monosubstituted benzene ring MSAESMALLA -GO FOR EXCELLENCEarmsalcedo2008 O R G A N I C C H E M I S T R Y .

2- 1.Aromatics Disubstituted 1.4- o- m- p- (ortho-) (meta-) (para-) MSAESMALLA -GO FOR EXCELLENCEarmsalcedo2008 O R G A N I C C H E M I S T R Y .3- 1.

Functional Groups hydrocarbon derivatives structural features that classify compounds by reactivity causes characteristic chemical behavior determines physical properties basis for naming organic compounds MSAESMALLA -GO FOR EXCELLENCEarmsalcedo2008 O R G A N I C C H E M I S T R Y .

replace –e with -ol MSAESMALLA -GO FOR EXCELLENCEarmsalcedo2008 O R G A N I C C H E M I S T R Y . followed by alcohol Name of parent as alkane.Alcohols R-OH General Formula: Nomenclature common: IUPAC: Name of parent alkyl.

Alcohols Classification 1° 3° 2° 1° alcohol 2° alcohol 3° alcohol MSAESMALLA -GO FOR EXCELLENCEarmsalcedo2008 O R G A N I C C H E M I S T R Y .

Alcohols MSAESMALLA -GO FOR EXCELLENCEarmsalcedo2008 O R G A N I C C H E M I S T R Y .

replace –yl with –oxy then name of the longer R as alkane MSAESMALLA -GO FOR EXCELLENCEarmsalcedo2008 O R G A N I C C H E M I S T R Y .Ethers R-O-R’ General Formula: Nomenclature common: Name of 2 alkyl groups in alphabetical order. followed by ether IUPAC: Name of shorter R group as alkyl.

Aldehydes General Formula: Nomenclature Name of parent as alkane. replace –e with -al IUPAC: MSAESMALLA -GO FOR EXCELLENCEarmsalcedo2008 O R G A N I C C H E M I S T R Y .

Ketone General Formula: Nomenclature Name of parent as alkane. replace –e with -one IUPAC: MSAESMALLA -GO FOR EXCELLENCEarmsalcedo2008 O R G A N I C C H E M I S T R Y .

replace –e with –oic + acid IUPAC: MSAESMALLA -GO FOR EXCELLENCEarmsalcedo2008 O R G A N I C C H E M I S T R Y .Carboxylic Acid General Formula: Nomenclature Name of parent as alkane.

Esters General Formula: Nomenclature Name of alkyl’. name of parent alkane replace – e with –oate IUPAC: MSAESMALLA -GO FOR EXCELLENCEarmsalcedo2008 O R G A N I C C H E M I S T R Y .

Br.Acid Halide General Formula: . Cl. where X is a halogen (F. I) Nomenclature Name of parent alkane replace –e with –oyl + name of halogen as halide IUPAC: MSAESMALLA -GO FOR EXCELLENCEarmsalcedo2008 O R G A N I C C H E M I S T R Y .

Acid Anhydride General Formula: Nomenclature Name of parent alkane replace –e with –oic + anhydride IUPAC: MSAESMALLA -GO FOR EXCELLENCEarmsalcedo2008 O R G A N I C C H E M I S T R Y .

Organic Nitrogen Compounds Amine General Formula: Nomenclature: name ending is -amine MSAESMALLA -GO FOR EXCELLENCEarmsalcedo2008 O R G A N I C C H E M I S T R Y .

Organic Nitrogen Compounds Amide General Formula: Nomenclature: name ending is -amide MSAESMALLA -GO FOR EXCELLENCEarmsalcedo2008 O R G A N I C C H E M I S T R Y .

Organic Nitrogen Compounds Nitrile General Formula: or Nomenclature: name ending is –nitrile (or cyanide) MSAESMALLA -GO FOR EXCELLENCEarmsalcedo2008 O R G A N I C C H E M I S T R Y .

Organic Sulfur Compounds Thiol General Formula: Nomenclature: name ending is –thiol MSAESMALLA -GO FOR EXCELLENCEarmsalcedo2008 O R G A N I C C H E M I S T R Y .

Summary Functional group General formula Suffix Example MSAESMALLA -GO FOR EXCELLENCEarmsalcedo2008 O R G A N I C C H E M I S T R Y .