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Nomenclature

Nomenclature

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Published by: Darice Wong on Mar 05, 2012
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Alkanes

CnH2n+2

ALKANES are compounds that contain only carbon-carbon and carbonhydrogen single bonds. The title shows the general formula for a chain alkane. The first ten alkanes are:

METHane CH4 ETHane

HEXane C6H12

C2H6HEPTane C7H16

PROPane C3H8OCTane
BUTane C4H10

C8H18
NONane C9H20 DECane C10 H22

PENTane C5H12

Lewis dot vs condensed formulas: propane.

H H H H C C C H CH3CH2CH3 H H H
Terminal carbons condense to CH3 with the hydrogens usually to the right of the carbon. Interior carbons condense to CH2.

Branching
A branch or substituents on a chain may be condensed into the chain usually after the carbon from which it branches.

CH3CH(CH3)CHClCH2CH3
H HCH H H H H H C C C C C H H H Cl H H

It is named by replacing the -ane of the alkane name with -yl. Methane becomes a methyl group. e.NOMENCLATURE Alkyl Groups H H C H H H H C or CH3 H An alkyl group is an alkane with one hydrogen atom removed. .g.

removal of a hydrogen generates two different propyl groups depending on whether an end or center H is removed. CH3 CH2 CH3 CH3CH2CH2 n-propyl CH3CH CH3 isopropyl .For PROPANE.

CH3 CH2 CH2 CH3 CH3 CH2 CH2 CH2 CH3 CH CH2 CH3 n-butyl sec-butyl .For BUTANE. gives two butyl groups depending on whether an end (1o) or interior (2o) H is removed.

CH3 CH3 CH CH3 CH3 1o CH3 CH CH2 isobutyl CH3 3o CH3 C CH3 tert-butyl .ISOBUTANE gives two butyl groups depending on whether a 10 or 30 H is removed.

Note: the longest chain may bend and twist. CH3 A CH2CH2CH CH2CH3 B CH3 CH2 CH3CH2CH2 CH2 CH3 CH3CH2CH CH2CH CH3 A. 8 carbons . – These carbon groups are also called alkyl groups. It is seldom horizontal! – Any carbon groups not part of the base chain are called branches or substituents. 7 carbons B. The base or parent name for an alkane is determined by the longest chain of carbon atoms in the formula.NOMENCLATURE 1.

2. If both branches are equally from the ends. Number the carbon atoms in the chain starting from the end with the first branch. 1 4 5 6 7 CH3 CH2 3 4 6 7 8 CH3 3 2 1 2 CH2CH2CH3 5 6 7 CH2CH2CH CH2CH3 CH3CH CH2CH CH2CH3 CH2 CH3 this branch would be on C-4 if you started at correct C-8 . continue until a point of difference occurs.

CH3 CH2 CH3 CH3 CH2 CH CH2 CH CH3 4-ethyl-2-methylhexane .Indicate the position of the branch on the main chain by prefixing its name with the carbon number to which it is attached. Halogens usually come first. .3. Separate numbers and letters with a hyphen. Prefix the branches/substituents in alphabetical order before the base/stem name (longest chain).

5-sec-butyl-4-isopropylnonane CH3 CH3 CH CH2 CH3 CH CH CH CH2 CH2 CH2 CH3 CH2 CH2 CH3 CH3 .Hyphenated and number prefixes are not considered when alphabetizing groups..

. etc. Separate numbers with commas. Then prefix the number to the name with a separate number for each occurrence.3-dimethylheptane NOTE: ethyl > dimethyl . tri-. CH3 CH2CH3 CH3CH CH CH2CH CH2CH3 CH3 5-ethyl-2. tetra-. prefix the name with di-.When a branch/substituents occurs more than once.

3-dimethyldecane .CH3 CH3CH CH3 CH2 CH2 CH3C CH2CH2C CH2CH3 CH3 CH2CH2CH2CH3 6-isobutyl-6-ethyl-3.

With the general formula of. Simplest alkyne: ethyne (acetylene) C2H2 . CnH2n. Simplest alkene: ethene (ethylene) C2H4 • ALKYNES have one or more carbon-carbon triple bonds.Alkenes and Alkynes • ALKENES are compounds that have carbon-carbon double bond framework.

CH3 CH2 CH3 3-ethyl-6-methyl-3-heptene CH3 CH CH2 CH C CH2 CH3 2-bromo-3-hexyne CH3CH C Br C CH2CH3 . Change -ane to -ene or -yne. Prefix the name with the number of the first multiple bond carbon. Prefix branch/substituent names as for alkanes.NOMENCLATURE Base name from longest chain containing the multiple bond. Number from the end that will give the first carbon of the multiple bond the lower number.

Substituents must have the lower possible numbers. Cl CH CH2 CH2 CH3 CH 5-chloro-3-methylcyclohexene CH CH . Prefix name with cyclo-.Cyclic alkenes are named like cyclic alkanes. Numbering MUST start at one end of the double bond and go THROUGH the bond.

the molecule did NOT react as if it had any UNSATURATION.Aromatic Hydrocarbons BENZENE‟s structure was first proposed by KEKULE in the 1850s. although his structures showed double bonds. CH3 NH2 NOMENCLATURE Toluene Certain groups change the base name of the ring system. C6H6. He proposed a CYCLIC structure for BENZENE. Kekule realized that there was something special about BENZENE because. Aniline OH COOH Phenol Benzoic acid .

NOMENCLATURE For monosubstituted benzenes. name the group and add “benzene”. NO2 Cl nitrobenzene CH2 CH3 chlorobenzene ethylbenzene .

An older system of naming uses ortho (o). and para (p) to indicate groups that are 1. The first named group is at position 1.4-dichlorobenzene p-dichlorobenzene NOTE: AS LONG AS YOU KNOW HOW TO NUMBER!. it must be number 1 on the ring.3 and 1. meta (m). 1.4 on the ring.For disubstituted benzenes.2. not necessary for the old name . If a “special group” is present. CH2 CH3 Br CH3 NO2 1-bromo-2-ethylbenzene o-bromoethylbenzene 3-nitrotoluene m-nitrotoluene Cl Cl 1. name the groups in alphabetical order.

it is called a PHENYL GROUP. Note the difference between phenyl and phenol (a functional group).When the benzene ring is a substituent on a chain (C6H5). CH2 CH CH2 CH CH3 4-phenyl-1-pentene .

CH3CH2OH CH3CH CH3 OH CH3 CH3 C CH3 OH Primary: ONE R group on the carbon attached to -OH Secondary: TWO R groups on the carbon attached to -OH Tertiary: THREE R groups on the carbon attached to -OH .ALCOHOLS AND PHENOLS Alcohols are classified as primary (1°). or tertiary (3°) depending on the number of carbon groups bonded to the hydroxyl bearing carbon. secondary (2°).

ALCOHOLS AND PHENOLS NOMENCLATURE Alcohols are classified as primary (1o). or tertiary. and write the name listing the substituents in alphabetical order. . depending on the numbers of carbon substituents bonded to the hydroxyl-bearing carbon: STEP 1 Select the longest chain containing the hydroxyl and replace the –e ending of the corresponding parent with –ol STEP 2 Number the carbons of the parent chain beginning at the end nearer the hydroxyl STEP 3 Number all substituents according to their position on the chain. secondary (2o).

The longest chain will be the parent structure (-ane). eg.ETHERS NOMENCLATURE Common names for ethers consist of the names of the two groups attached to the O listed in alphabetical order (or size) and followed by „ether‟. (alkane with the ane replaced by oxy. CH3CH2O = ethoxy). CH3CH2CH2CH2CH2-O-CH3 CH3CH2-O-CH2CH2CH2CH3 1-methoxypentane 1-ethoxybutane methyl pentyl ether ethyl butyl ether . The shorter chain is named as an alkoxy substituent. Each part is a separate word O CH3 CH3CH – O – CH3 Ethyl phenyl ether tert-Butyl methyl ether The IUPAC names for ethers are based on the alkane name of the longest chain attached to the O.

and sulfides. 3D CH3 CH3 – CH .THIOLS Thiols (mercaptans). R-SH.CH2 – CH2 SH 3-methyl-1-butanethiol . the mercaptan group. are sulfur analogs of ether. are sulfur analogs of alcohols. The SH group is variously called the thiol group. RSR‟. or the sulfuhydryl group. NOMENCLATURE Name based on the longest alkane chain with the suffix position indicated by a number.

C=O O R C R Aldehydes: R may be hydrogen usually a carbon containing group O R C H RCHO O R C R RCOR Ketones: R contains carbon .CARBONYL COMPOUNDS • contains the carbonyl group.

Aldehydes NOMENCLATURE STEP 1 Select the longest carbon chain containing the carbonyl carbon.) Name the substituents attached to the chain in the usual way. The carbonyl carbon is always numbered “1. The -e ending of the parent alkane name is replaced by the suffix -al. STEP 2 STEP 3 STEP 4 O CH3CH Ethanal (Acetaldehyde) O CH3CH2CH Propanal (Propionaldehyde) O CH3CH CH2CH2CH 1 H2C 5 CH 3 4 3 2 4-methylhexanal 6 .” (It is not necessary to include the number in the name.

KETONES NOMENCLATURE STEP 1 Naming the two alkyl groups attached to the carbonyl in a) alphabetical order or b) by increasing size. O CH3 C CH2 CH3 STEP 2 Methyl ethyl ketone or Ethyl methyl ketone Longest chain with the C=O. STEP 3 Cl O 4-chloro-2-pentanone CH3CH CH2C CH3 . The corresponding alkane is (-e) is replaced with -one The position of C=O by number of chain is indicated.

or aromatic .CARBOXYLIC ACIDS O C OH or -CO2H or -COOH carboxyl group O S OH or -SO3H O sulfonic acid group O R C OH R = may be H. alkyl.

O CH3 CH3 CH CH2 C OH 4 3 2 1 3-methylbutanoic acid .NOMENCLATURE Start numbering at the -COOH carbon. Replace the -e of the alkane name with oic acid.

or. alkyl. alkyl. aromatic . aryl ACID CHLORIDES O R1 C Cl R1 may be H. R2. R3 may be H.The Acid Derivatives AMIDES O R1 C N R2 R3 R1.

The Acid Derivatives ACID ANHYDRIDE O O R C O CR R may be alkyl or aryl ESTERS O R1 C O R2 R2 may not be H .

or aromatic .ESTERS Esters are derivatives of an ACID and an ALCOHOL that can also be hydrolyzed to these parent compounds. ESTER LINKAGE O R C OR R = may be alkyl.

O CH3CH2C O CH2CH3 ethyl propanoate . Base name for the acid part of the structure from the longest chain ending in the C=O. (Alcohol part of the ester). Change the oic acid of the acid name to oate and add this to the name in 1 as a second word.NOMENCLATURE Name the alkyl group attached to the oxygen atom first.

the smaller groups on the amine nitrogen are designated as substituents and given the locant N .AMINES NOMENCLATURE • Primary amines are named in systematic (IUPAC) nomenclature by replacing the -e of the corresponding parent alkane with -amine • In common nomenclature they are named as alkylamines • Simple secondary and tertiary amines are named in common nomenclature by designating the organic groups separately in front of the word amine • In systematic nomenclature.

NOMENCLATURE • In IUPAC nomenclature the substituent -NH2 is called the amino group .

• In IUPAC nomenclature the prefixes aza-. . diaza.NOMENCLATURE Heterocyclic Amines • The important heterocylcic amines have common names.are used to indicate that nitrogen has replaced carbon in the corresponding hydrocarbon.and triaza. The nitrogen is assigned position 1 and the ring is numbered to give the lowest overall set of locants to the heteroatoms.

NOMENCLATURE Heterocyclic Amines .

STEP 2 Remove –ic acid (common) or –oic acid (IUPAC) and replace with –amide. STEP 3 Nitrogen substituents are prefixed to the name and indicated by N. O CH3C NH2 ethanamide or acetamide O CH3CH2C NH CH3 N-methylpropanamide .AMIDES NOMENCLATURE STEP 1 Names are derived from the acid.

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