Organic Nomenclature

Compounds in which carbon is the

principal element.
Writing formulas. . .
 Condensed: CH3CH(CH3)CH = CHCH(CH3)CH3

H H
 Kekule’ H C C H
H H

 Skeletal
Hydrocarbons. . .
 Contain only hydrogen and carbon.
 Types:
 Alkane: single bonds; saturated (largest possible number of
hydrogens/carbon atom. [CnH2n+2]
H H
 Alkene: one or more carbon-carbon double bond. Unsaturated
H C C H
hydrocarbon. H H

H H H
 H C C Unsaturated
Alkyne: one carbon-carbon triple bond. C
hydrocarbon. H
H
 Aromatic: carbon atoms connected in a planar ring. Unsaturated
hydrocarbon.
Hydrocarbons. . .
 Relatively nonpolar. (covalent bonds)
 Insoluble in water. (like dissolves like)
 Less volatile with increasing molar
mass. (because of London dispersion forces)
Alkanes. . . [CnH2n+2]
 Methane: CH4 major component of natural gas;
home heating; gas stoves; hot water heaters
 Ethane: C2H6 H H
H C C H
H H
 Propane: C3H8 used for home cooking and
heating; gas grills
 Butane: C4H10 disposable lighters and fuel
canisters for gas camping stoves.
Name consists of. . .
 1. Prefix
 Where are the substituents?
 [Link]
 How many carbons in the longest chain?
 3. Suffix
 Which family?
 If two different chains of equal length are present:
 choose the one with the larger number of branch points as
the parent.
Rules for naming alkanes. . .
Longest continuous chain of carbon atoms gives the root name
1. For alkanes, add –ane to the root:
Meth: C
Eth: C2
Prop: C3
But: C4
2. For alkanes beyond butane, use the Greek root for
the number of carbons then add -ane to the end.
C-C-C-C-C-C = hexane
pent=5; hex=6; hept=7; oct=8; non=9; dec= 10
Substituent

Group(s) added in place of a

removed hydrogen.
Alkanes as a substituent
group. . .
Alkyl substituents:
1. Remove a hydrogen from the
alkane.
C2H6 is ethane
2. Drop the -ane and add -yl.
-C2H5 is ethyl
Positions of substituent groups are
specified by numbering the longest
chain sequentially. (Use the lowest number for the
position of the substituent group)
C
C-C-C-C-C-C
3-methylhexane
The location and name of the
substituent group is followed by root
alkane name.
Substituents in alphabetical order.
Use di-, tri-, etc. to indicate multiple
identical substituents.
Practice. . .write skeletal and
condensed formulas.
 2,3-dimethylhexane
 2-ethyl-3-methylpentane
 4-ethyl-3,5-dimethylnonane
 4-tert-butylheptane
 2,3-dimethylpentane
Cyclic Alkanes. . . CnH2n
 Cycloalkanes
 Smaller than five carbons, very reactive.
 Rings of carbon atoms.
 Isomers
 Cis: both substituents are on the same side of
the ring.
 Trans: substituents are on opposite sides of the
ring.
Reactions of Alkanes. . . .
 Combustion: react with oxygen produce
carbon dioxide and water
 Substitution: halogen atoms replace
hydrogen atoms
 Dehydrogenation reactions:hydrogen
removed forms double bond there
unsaturated hydrocarbon is the product
Alkenes. . .
 1. Root hydrocarbon (longest chain containing double
bond) name ends in –ene.
 2. More than three carbon atoms, the location of the
double bond is indicated by the lowest numbered
carbon atom in the bond. If equidistant: begin at end
closer to substituent group.
 CH2=CHCH2CH3 1-butene
 CH3CH=CHCH3 2- butene
 3. More than one double bond
 Indicate the position of each and use –diene, triene,
tetraene. . .
Cycloalkenes. . .
 Name same as alkenes.
 Number so double bond is between C1
and C2 and the first substituent has the
lowest number possible.
Practice. . .write the skeletal
formula and name.
 CH2=CHCH(CH3)C(CH3)(CH3)CH3

 CH3CH2CH=C(CH3)CH2CH3

 CH3CH=CHCH(CH3)CH=CHCH(CH3)CH3
Practice. . .
 2-methyl-1,5-hexadiene
 3-ethyl-2,2dimethyl-3-heptene
 2,3,3-trimethyl-1,4,6-octatriene
 4-tert-butyl-2-methylheptane
 3,4-diisopropyl-2,5-dimethyl-3-hexene
Practice. . .
CH3
CH3

CH(CH3)2

CH3

CH3
Alkynes. . .
 Unsaturated hydrocarbons contain atleast one
triple carbon-carbon bond.
 -yne replaces –ane.
 Begin numbering chain at end closest to triple
bond.
 More than one bond: -diynes, -triynes.
 Double and triple bonds: -enynes
 Start numbering from end nearer first bond. (if
there is a choice. Usually double bonds get lower
numbers than triple.)
Practice. . .
 CH3CH(CH3)C CCH(CH3)CH3
 CH CC(CH3)(CH3)CH3
 CH3CH=CHCH=CHC CCH3
 CH3CH2C(CH3)(CH3)C CCH2CH2CH3
Practice. . .
Reactions of Alkenes and
Alkynes. . .
 Addition reactions: double bond broken and new
bonds formed to atoms added.
 Hydrogenation reactions: addition of hydrogen atoms
 Halogenation: addition of a halogen
 Elimination:one reactant splits apart to give two
products.
 Substitutions: two reactants exchange parts to give
two new products.
 Rearrangement:one reactant undergoes a
reorganization of bonds and atoms to give a new
product.
Aromatic Hydrocarbons. . .
Benzene and its structural relatives

 Monosubstituted benzene: named as other

hydrocarbons, with benzene as parent name.
 If substituent larger than ring (six carbons) :
benzene becomes substituent group called phenyl.
 Disubstituted benzene: ortho:1,2 meta-1,3
para-1,4
 More than two: number the position of each
substituent group.
Hydrocarbon derivatives. . .
 Alcohols: presence of an –OH (hydroxyl group)
 Nomenclature: replace final -e of parent
hydrocarbon with –ol.
 (parent: longest chain containing –OH)
 Position of –OH specified by number.
 Number is lowest of substituent groups.
 Classified by: number of hydrocarbon fragmennts
bonded to carbon where –OH group is attached.
 R,R’,R”represent the hydrocarbon fragments.
Alcohols. . . .
 Polar
 Higher boiling points than expected
from molecular weights.
 Intermolecular attractions. –OH
extensive hydrogen bonding.
Practice. . .
 CH3C(OH)(CH3)CH2CH2CH3

 2methyl-2-pentanol

 CH3CH(OH)CH2CH(OH)CH(CH3)2

 5-methyl-2,4-hexanediol
Practice. . .
 2-ethyl-2-buten-1-ol

 3-cyclohexen-1-ol

 trans-3-chlorocycloheptanol

 1,4-pentanediol
 Practice. . .
CH3
OH
CH3
4,4-dimethylcyclohexanol

CH2CH2C(OH)(CH3)2

2-methyl-4-phenyl-2-butanol
Aldehydes. . .
 Nomenclature: remove –e replace with –al.
 Longest chain as base name,must contain the
carbonyl group. Aldehyde carbon assigned
number 1, when subtituent positions are
listed in the name.
 Bonded to at least one hydrogen atom.
 Number indicates position of carbonyl group.
 -CHO group attached to a ring, suffix
-carbaldehyde.
Practice. . .
 CH3CHO
 Ethanal

 CH3CH2CHO
 Propanal

 CH3CH(CH3)CH2CH(CH2CH3)CHO
 2-ethyl-4-methylpentanal
Practice. . .

CHO

Cyclohexanecarbaldehyde

CHO

benzenecarbaldehyde
Ketones. . .
 Contain carbonyl group bonded to two carbon
atoms
 Final –e replaced with -one.
 Longest chain with ketone group is the
parent.
 Numbering begins at the end nearest the
carbonyl carbon.
 If ketones is the substituent group, -acyl is
used and the name ending –yl is attached.
Practice. . .
 CH3CH=CHCH2COCH3
 4-hexen-2-one
 CH3CH2COCH2COCH3
 2,4-hexanedione
 CH3CH2COCH(CH3)2
 2-methyl-3-pentanone
 CH3COCH2CH2CH2COCH2CH3
 2,6-octanedione
Practice. . .
 OHCCH2CH2CH2CHO
 Pentanedial
 CH3CH2CH(CH3)CH(CH2CH2CH3)COCH3
 4-methyl-3propyl-2-hexanone
 CH3CH=CHCH2CH2CHO
 4-hexenal
Practice. . .
 3-methylbutanal

 3-methyl-3-butenal

 4-chloro-2-pentanone
Carboxylic Acids. . .
 Two systems:
 Derived from open chain alkanes:
 Carboxyl carbon is always C1.
 Replace terminal –e of alkane with –oic
acid.
 -COOH group bonded to a ring, the suffix
–carboxylic acid is used. The carboxylic
acid carbon is attached to C1 and is not
itself numbered in this system.
Practice. . .
 CH3CH(CH3)CH2CH2COOH

 4-methylpentanoic acid

 HOOCCH2CH(CH2CH3)CH2CH2CH(CH3)CH2COOH

 3-ethyl-6-methyloctanedioic acid
Practice. . .
 (CH3)2CHCH2COOH
 3-methylbutanoic acid
 CH3CHBrCH2CH2COOH
 4-bromopentanoic acid
 CH3CH=CHCH=CHCOOH
 2,4-hexadienoic acid
 CH3CH2CH(COOH)CHCH2CH2CH3
 2-ethylpentanoic acid
Practice. . .
COOH

3-bromocyclohexanecarboxylic acid

Br

COOH

1-cyclopentenecarboxylic acid
Carboxylic Acids. . .
 Strong hydrogen bonding has a
noticeable effects on boiling points.
 Much higher than corresponding
alcohols.
Isomerism