ORGANIC NOMENCLATURE RULES

Alkanes:
1. Determine the longest continuous (not necessarily drawn straight) chain of carbon atoms in the molecule. The parent name
of the compound uses the appropriate prefix for the number of carbons as indicated in the chart below, followed by the suffix
–ane.
# Carbons 1 2 3 4 5 6 7 8 9 10
Main Chain meth- eth- prop- but- pent- hex- hept- oct- non- dec-
2. Any carbon chain on the parent chain (longest chain) is considered a branch. It is also referred to as an alkyl group. It is
named with the appropriate prefix for the number of carbons as indicated in the chart below & the suffix –yl.
# Carbons 1 2 3 4 5 6 7 8 9 10
Branch Name methyl ethyl propyl butyl pentyl hexyl heptyl octyl nonyl decyl
3. The complete name of a branch requires a number that locates the branch on the parent chain. For this purpose, number
each carbon atom on the parent chain in the direction that gives the lowest numbers to all the branches. A methyl branch
located on the third carbon of octane is 3-methyl, & the compound is named 3-methyloctane. NOTE THE CORRECT USE
OF HYPHENS & THAT THE NAME IS ALL ONE WORD.
4. When there is more than one of the same sized alkyl group (i.e., two methyl C C
groups), the alkyl group name includes di-, tri-, tetra-, etc., to indicate the C C C C C C C C C C
number. The position of each group on the parent chain is given by its C C
position number, in numerical order. NOTE THE CORRECT USE OF 2,3-dimethylpentane 2,2-dimethylpentane
COMMAS & HYPHENS.
5. When there are two or more different alkyl groups, the names & numbers of all the C

branches precede the parent name. The branch names are placed in alphabetical C
C C C C C C C
order by alkyl group (di-, tri-, tetra-, etc., are ignored). C
6. When there are two possible numbering systems for the same molecule, the 4-ethyl-3-methylheptane
lowest number goes to the first branch. C C C C C C C
C C
C
3-ethyl-5-methylheptane
Alkenes:
1. Find the longest chain containing the double bond(s). This longest chain gives you the parent name, but with the suffix –
ene rather than –ane. The carbon atoms of the longest chain are numbered to give the double bond(s) the lowest possible
number(s). The position of the double bond is indicated as the number of the first carbon atom of that bond. This number is
written in front of the base name of the alkene.
2. If there is more than one double bond, the number of the first carbon of each bond is
included, & the suffix –ene is preceded by di-, tri-, tetra-, etc., to indicate the number of C C C C C
double bonds. NOTE THE CORRECT POSITION OF “DI” IN THE EXAMPLE. 1,3-pentadiene
3. All branches are alkyl groups & are named accordingly. The branch numbers
C
correspond to the numbers from step 1. The double bonds have priority in the
numbering, so the branch numbers may be higher than they would be for an alkane. C C C C C
NOTE THE NUMBERING FOR THE ALKYL GROUP & THE DOUBLE BOND. 4-methyl-1-pentene

Cis & Trans Geometric Isomers:

1. In circumstances where the longest chain occurs on the same side of a double bond, C
then the prefix cis must precede the location where the double bond occurs. If the chain C C C C
occurs on opposite sides of a double bond, the prefix used is trans is used. NOTE THE C C C
CORRECT USE OF CIS & TRANS. cis-2-butene trans-2-butene
2. It should be noted that not all alkenes have cis or trans isomers, such as when the double bond is at the end of a molecule
(assuming there is no cyclic or other functional group present on the first carbon where the double bond is located), or when
it is unknown due to the way the molecule is drawn.

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Alkynes:
1. Alkynes are named by IUPAC rules in the same way as the alkenes, except that the parent name is determined from the
longest chain containing the carbon-carbon triple bond. The suffix for the parent names of alkynes is –yne.

Cyclic Hydrocarbons:
1. If a hydrocarbon structure contains a completed ring with branches on the ring structure, the ring structure becomes the
parent chain with the prefix “cyclo” preceding it. Name all branches following regular nomenclature rules.
2. If the ring structure is a branch, or if there is more than C

one ring structure, use “di”, “tri”, etc., along with the C C C C C

prefix “cyclo”, & end with “yl” to name the ring structure
as a branch.
1,2,4-trimethylcyclohexane 2,4-dicyclopentyl-2-methylpentane
3. Cyclic structures typically contain single bonds, but can contain double bonds if the ring structure has sufficient size (5 or
more carbon atoms) to accommodate the bond angle strain. Typically double bonds in cyclic structures tend to be cis while
triple bonds are not found in cyclic structures. Both are due to bond angle strain.

Benzene-Based (Aromatic) Hydrocarbons:

1. Name the branches as usual, ending in benzene. Apply the smallest sum rule if more than one alkyl group exists on the
benzene ring.
2. If the molecule has more than one benzene ring, select the central part of the molecule as the parent chain. Number the
carbons on the parent chain so that the benzenes have the lowest possible number.
3. Benzene rings are branches are called “phenyl”. Name the rest
of the molecule as usual.
2-methyl-1-phenylpentane 1-methyl-2-pentylbenzene
Alkyl Halides:
1. Find the longest chain containing the C atom to which the halogen is attached.
2. Number the C atoms to give the halogen the lowest possible number.
3. Name the branches as usual.
4. Write the number for the halogen, followed by “fluoro”, “bromo”, “chloro” or “iodo” before the base name, keeping the
aliphatic name as the base.
5. For more than one halogen, include both numbers, keep the
alkane name & add “di”, “tri”, etc., before the name of the halogen.
2-bromo-1-iodobutane 4-fluoro-2-methyl-2-pentene
Alcohols:
1. Find the longest chain containing the C atom to which the OH is attached.
2. Number the C atoms to give the OH the lowest possible number.
3. Name the branches as usual.
4. Write the number for the location of the OH before the base name, keep the alkane name as the base, but replace the “e”
with “ol”.
5. For more than one OH, include both numbers, keep the alkane name & add “di”, “tri”, etc., before the “ol”.

Alternate Naming of Alcohols:

If the OH group is named as a branch, then write the number for the location of the OH group, followed by “hydroxy” then the
name of the parent. If more than one branch is present, usual naming rules apply.
IUPAC name Alternate name
1,3-pentanediol 1,3-dihydroxypentane

4-hexyn-3-ol 3-hydroxy-4-hexyne

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Ethers:
1. Choose the longest C chain to be the base.
2. Number the chain to give the O the lowest possible number & write that number at the beginning of the name. (It is not
necessary to write “1” if the O is at the end of the longest chain).
3. Name the shorter chain as branch, replacing the usual suffix “yl” with the suffix “oxy”.
4. Name the base as you would a regular hydrocarbon.
 General format: (name of short alkyl group, ending in “oxy”)(name of longer alkyl group)

2-cyclobutoxypentane 1-(2-butoxy)-2-methylhexane

Aldehydes:
1. Find the longest C chain that contains the C=O group.
2. Number the chain starting at the C in the C=O group. (Writing the location of the carbonyl group is redundant)
3. Name any branches as usual.
4. Name the base as a regular hydrocarbon, but change the suffix to “al”.

pentanedial 3-bromopropanal

Ketones:
1. Locate the longest C chain that contains the C=O group.
2. Number the C atoms to give the smallest number to the position of the C=O group.
3. Name any branches as usual.
4. Place the number of the C=O before the base name, keep the alkane name & replace the “e” with “one”.
5. If there is more than one C=O, number both, keep the alkane name & use “di”, “tri”, etc., before the suffix “one”.

4-hydroxy-2-pentanone 2,3-pentanedione 1-cyclohexyl-1-propanone

Carboxylic Acids:
1. Select the longest base that includes the carboxyl group—it will always be on the end.
2. Number the C atoms starting with (& including) the C in the carboxyl group.
3. Name any branches as usual.
4. In the base name, the final “e” from the hydrocarbon name is
replaced by “oic acid”.
3-methylheptanoic acid propanedioic acid
Esters:
1. Find the name of the alcohol that reacted to form the ester (the C chain without the C=O) & change its suffix to “yl”.
2. Determine the name of the carboxylic acid that reacted & change the suffix from “oic acid” to “oate”.
3. Combine the two into the ester name using two words.

ethyl 2-methylpentanoate 2-methylpentyl ethanoate

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Amines:
IUPAC: (name mostly as a branch)
1. Number the longest chain connected to the NH2 to give the N the lowest possible number.
2. Name the NH2 branch as “amino”. Name all other branches as usual.
3. If there is more than one NH2, number all of them. Use “di”, “tri”, etc . Write it all as one name.
4. For 2° & 3° amines, use the notation: N-alkylamino as the branch name. The “N” means the alkyl group is located on the
amino group. You are still required to indicate the numerical location of the N-alkylamino group on the parent chain. It is all
one word.

Chemical Abstract Service, CAS: (name mostly as a main chain)

1. Number the longest chain connected to the NH2 to give the N the lowest possible number.
2. Name branches as usual.
3. The number for the NH2 goes before the base name. In the base name, the final “e” from the hydrocarbon name is replaced
by “amine”.
4. If there is more than one NH2, number all of them. For the suffix, keep the alkane name, followed by “di” or “tri” & finally
“amine”. Write it all as one name.
5. For 2° & 3° amines, use N- to indicate the location of the alkyl groups on N. It is all one word.
IUPAC name CAS name
1-aminopentane pentanamine

2-amino-2-methylpropane 2-methyl-2-propanamine

1-methylaminopropane N-methylpropanamine

dimethylaminoethane N,N-dimethylethanamine

Amides:
1. Determine the length of the carbon chain(s) on the amine that reacted to form the amide. Give it the suffix “yl” & designate it
as a branch located on “N”.
2. Determine the name of the carboxylic acid that reacted & changed the suffix from “oic acid” to “amide”.
3. Combine the two into the amide name. If there are two branches on the “N”, write them in alphabetical order.
Note: If the amide was formed with ammonia, only the second rule applies.

N-methyl-N-propylbutanamide 3-methylbutanamide 3,N-dimethylbutanamide

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 FUNCTIONAL GROUP SUMMARY
Order of Priority for Numbering Carbons on a Carbon Chain for Functional Groups
Suffix
Order of Functional Prefix
Type of Molecule Formula (if naming as a main
Priority Group (if named as a branch)
chain)

1 carboxylic acid -COOH carboxy___ ___oic acid

R-oxycarbonyl___
2 ester -COOR ___oate
(i.e., propoxycarbonyl___)

3 amide -CONH2 carbamoyl___ ___amide

4 nitrile -CN cyano___ ___nitrile

5 aldehyde -CHO formyl___ ___al

6 ketone -CO oxo___ ___one

7 alcohol -OH hydroxy___ ___ol

8 amine -NH2 amino___ ___amine

alkenyl___ or alkynyl___
9 alkene & alkyne = or ≡ (i.e., propenyl___ or ___ene or ___yne
propynyl___)

10 ether -OR ___oxy___

fluoro___, chloro___, ___fluoride, ___chloride,
11 halogen -X
bromo___, iodo___ ___bromide, ___iodide
12 nitro -NO2 nitro___
___yl
alkyl (carbon chains,
13 -R (i.e., propyl) (if aromatic, ___benzene)
including phenyl)
(if aromatic, phenyl___)
(The general rule is to give the lowest number to the suffix of the organic molecule name).

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 PERIODIC TABLE
(Electronegativities, Common Valences, Atomic Masses)
1 (IA) 18 (VIIIA)

1 2.20 2 0
1+, 1-

H He
Hydrogen 2 (IIA) Legend 13 (IIIA) 14 (IVA) 15 (VA) 16 (VIA) 17 (VIIA) Helium
1.01 4.00
3 0.98 4 1.57 Atomic # EN 5 2.04 6 2.55 7 3.04 8 3.44 9 3.98 10 0
1+ 2+ Common Valences  Most stable valence is bolded 3+ 4, 2+ 1+. 2-, 3+, 3-, 4-, 5- 2-, 1- 1-

Li Be Symbol B C N O F Ne
Lithium Beryllium Atomic Name Boron Carbon Nitrogen Oxygen Fluorine Neon
6.94 9.01 Atomic Mass 10.81 12.01 14.01 16.00 19.00 20.18
11 0.93 12 1.31 13 1.61 14 1.90 15 2.19 16 2.58 17 3.16 18 0
1+ 2+ 3+ 4 3+, 3-, 4-, 5- 2+, 2-, 6- 1+, 1-, 3-, 5-, 7-

Na Mg Al Si P S Cl Ar
Sodium Magnesium 3 (IIIB) 4 (IVB) 5 (VB) 6 (VIB) 7 (VIIB) 8 (VIIIB) 9 (VIIIB) 10 (VIIIB) 11 (IB) 12 (IIB) Aluminum Silicon Phosphorus Sulphur Chlorine Argon
22.99 24.31 26.98 28.09 30.97 32.07 35.45 39.95
19 0.82 20 1.00 21 1.36 22 1.54 23 1.63 24 1.66 25 1.55 26 1.83 27 1.88 28 1.91 29 1.90 30 1.65 31 1.81 32 2.01 33 2.18 34 2.55 35 2.96 36 0
1+ 2+ 3+ 3+, 4+ 2+, 3+, 4+, 5+ 2+, 3+, 6+ 2+, 3,+, 4+, 6+, 7+ 2+, 3+ 2+, 3+ 2+, 3+ 1+, 2+ 2+ 3+ 4 3+, 3-, 5- 2-, 4-, 6- 1+, 1-, 5-

K Ca Sc Ti V Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr
Potassium Calcium Scandium Titanium Vanadium Chromium Manganese Iron Cobalt Nickel Copper Zinc Gallium Germanium Arsenic Selenium Bromine Krypton
39.10 40.08 44.96 47.88 50.94 52.00 54.94 55.85 58.93 58.69 63.55 65.39 69.72 72.61 74.92 78.96 79.90 83.80
37 0.82 38 0.95 39 1.22 40 1.33 41 1.60 42 2.16 43 1.90 44 2.20 45 2.28 46 2.20 47 1.93 48 1.69 49 1.78 50 1.96 51 2.05 52 2.10 53 2.66 54 0
1+ 2+ 3+ 4+ 3+, 5+ 2+, 3+, 4+, 5+, 6+ 2+, 3+, 4+, 6+, 8+ 2+, 3+, 4+ 2+, 4+ 1+ 2+ 3+ 2+, 4+ 3+, 3-, 5- 2-, 4-, 6- 1+, 1-, 5-, 7-

Rb Sr Y Zr Nb Mo Tc Ru Rh Pd Ag Cd In Sn Sb Te I Xe
Rubidium Strontium Yttrium Zirconium Niobium Molybdenum Technetium Ruthenium Rhodium Palladium Silver Cadmium Indium Tin Antimony Tellurium Iodine Xenon
85.47 87.62 88.91 91.22 92.91 95.94 (98.91) 101.07 102.91 106.42 107.87 112.41 114.82 118.71 121.75 127.60 126.90 131.29
55 0.79 56 0.89 71 1.27 72 1.30 73 1.50 74 2.36 75 1.90 76 2.20 77 2.20 78 2.28 79 2.54 80 2.00 81 2.04 82 2.33 83 2.02 84 2.00 85 2.20 86 0
1+ 2+ 2+ 4+ 5+ 2+, 3+, 4+, 5+, 6+ 1-, 2+, 4+, 6+, 7+ 2+, 3+, 4+, 6+, 8+ 2+, 3+, 4+, 6+ 2+, 4+ 1+, 3+ 1+, 2+ 1+, 3+ 2+, 4+ 3+, 5+ 2+, 4+ 1+, 1-, 3-, 5-, 7-

Cs Ba Lu Hf Ta W Re Os Ir Pt Au Hg Tl Pb Bi Po At Rn
Cesium Barium Lutetium Hafnium Tantalum Tungsten Rhenium Osmium Iridium Platinum Gold Mercury Thallium Lead Bismuth Polonium Astatine Radon
132.91 137.33 174.97 178.49 180.95 183.85 186.21 190.23 192.22 195.88 196.97 200.59 204.38 207.2 208.98 (208.98) (209.99) (221.02)
87 0.70 88 0.90 103 104 105 106 107 108 109 110 111 112 113 114 115 116 117 118
1+ 2+ 3+

Fr Ra Lr Rf Db Sg Bh Hs Mt Ds Rg Cn Nh Fl Mc Lv Ts Og
Francium Radium Lawrencium Rutherfordium Dubium Seaborgium Bohrium Hassium Meitnerium Darmstadtium Roentgenium Copernicium Nihonium Flerovium Moscovium Livermorium Tennessine Oganesson
223.02 226.03 (260.11) (261.11) (262.12) (263.12) (262.12) (264) (266.14) (269) (272) (277) (285) (289)

57 1.10 58 1.12 59 1.13 60 1.14 61 1.13 62 1.17 63 1.20 64 1.20 65 1.20 66 1.22 67 1.23 68 1.24 69 1.25 70 1.11
3+ 3+, 4- 3+, 4+ 3+ 3+ 2+, 3+ 2+, 3+ 3+ 3+, 4+ 3+ 3+ 3+ 2+, 3+ 2+, 3+

La Ce Pr Nd Pm Sm Eu Gd Tb Dy Ho Er Tm Yb
Lanthanum Cerium Praseodynium Neodymium Promethium Samarium Europium Gadolinium Terbium Dysprosium Holmium Erbium Thulium Ytterbium
138.91 140.12 140.91 144.24 144.91 150.36 151.96 157.24 158.93 162.50 164.93 167.26 168.93 173.04
89 1.10 90 1.30 91 1.50 92 1.38 93 1.36 94 1.28 95 1.30 96 1.30 97 1.30 98 1.30 99 1.30 100 1.30 101 1.30 102 1.30
3+ 4+ 4+, 5+ 3+, 4+, 5+, 6+ 3+, 4+, 5+, 6+ 3+, 4+, 5+, 6+ 3+, 4+, 5+, 6+ 3+ 3+, 4+ 3+ 3+ 3+ 2+, 3+ 2+, 3+

Ac Th Pa U Np Pu Am Cm Bk Cf Es Fm Md No
Actinium Thorium Protactinium Uranium Neptunium Plutonium Americum Curium Berkelium Californium Einsteinium Fermium Mendelevium Nobelium
227.03 232.04 231.04 238.03 237.05 224.06 243.06 247.07 247.07 251.08 252.08 257.10 258.10 259.10

100