Naming Hydrocarbons

(nomenclature)

Handout: Hydrocarbons: IUPAC names

Drawing structures: it’s all good
H
C

2-butene
H
H

H

C

C

C

C

H

H

H

H

H3C
H

H3C CH CH CH3

C
H

CH
H3C
H3C

CH

CH3

CH3
CH3

This is called the
“condensed structure” On a test, choose a method
that shows all Hs

CH3CH=CHCH3
Using brackets can also shorten some formulas:
CH3(CH2)4CH3 vs. CH3CH2CH2CH2CH2CH3

2 = 10 .Background: formulas for HCs • Alkanes= CnH2n+2.how many hydrogens in each of these: 6 carbon alkane 14 Alkene: C22H 44 H3C CH3 8 (2x5 . propyne vs. propadiene) Q . • Provides some useful information (e. ynes= CnH2n-2 • Remember enes. enes= CnH2n.g.2) . or to check work) • Cannot always tell hydrocarbon type based on numbers (e. then think of what would happen if bond was single or triple instead. for compositional analysis.g.

Naming: common vs. IUPAC • Common names used in the 1800’s are still used for some compounds today: O O H C H OH Formic acid C C Acetylene H C H3C CH3 Acetone • The International Union of Pure and Applied Chemistry (IUPAC) was established in 1900s • Frequent revisions to nomenclature • Systematic method allows an infinite number of compounds to be named given a few rules .

or -yne • 2) the number of carbons is given by a “Prefix” 1 meth.2 eth. but a is dropped when next to a vowel.7 hept.9 non.What names would be given to these: 7C. 3C alkene does not exist. 3) side chain type and 4) position • 1) name will end in -ane.5 pent6 hex.4 but. propene . butyne 1C. all end in a.Basic names of hydrocarbons • Hydrocarbon names are based on: 1) class 2) # of C.g.10 dec• Actually.8 oct.3 prop. a 6 C alkene is hexene Q . E. 9C alkane heptane. nonane 2C. 4C alkyne ethyne. -ene.

Mnemonic for first four prefixes First four prefixes • • • • MethEthPropBut- Monkeys Eat Peeled Bananas .

Hept-. Non- .Other prefixes ? Decade Decimal Decathalon • Pent• Oct• Dec• Hex-.

Numbering carbons Q.Where’s the bond? We number C atoms H3C 5 1 H H 1-pentene C C C C H H H H 4 2 3 2 4 1 5 H • Thus. are #s needed • Always give double bond the lowest number • Q . naming compounds with multiple bonds is more complex than previously indicated • Only if 2+ possibilities exist.draw pentene A.Name these 2-butene H3C H3C C H H C C2H4 CH3 Ethene CH3 3-nonyne .

tri.6-nonatriyne • • • • CH2 CH3 Give 1st bond (1st point of difference) lowest # include di. tetra.4-pentatriene CH3CH2CH2CH=C=CH2 1. penta.3-heptadiene H3C C C C C C C 2. hyphen between #-letter You do not need to know ene + yne H H C H C C C HC 2-butyne H H2C C CH2 CH 1. before ene/yne Comma between #s.2. etc.Multiple multiple bonds H3C CH3 2.2-hexadiene H H .4.

3-cyclopentadiene cyclopropane H H H2C CH2 HC CH H H C C C H C C H CH2 H H2C CH2 .): cyclobutene 1. 5 and 6. etc.Draw these (note: carbons in a double bond should be consecutive.1 and 2.Cyclic structures H H H H C C C H • Cyclic structures are circular C C • Have “cyclo” in name H H H H • Benzene is not a cyclic structure • cyclopentane Q.

I.propyl (CH3)2CH.(bromo). root • 2. Cl.(fluoro).(iodo) .(chloro).3-dimethylpentane CH3 • Root is the longest possible HC chain • Must contain multiple bonds if present • Add -yl to get name of side chain H3C CH3 • Common side chains include: CH CH3.ethyl * CH3CH2CH2. F.Naming side chains CH3 H3C CH3 • Names are made up of: side chains.methyl CH3CH2.isopropyl • “iso” (branched) is not an IUPAC convention • Br.

Naming side chains Example: use the rules on the bottom of handout to name the following structure CH2 CH3 CH2 C CH2 CH3 CH2 C CH3 CH3 Rule 1: choose the correct ending ene .

Naming side chains CH2 CH3 CH2 C CH2 CH3 CH2 C CH3 CH3 Rule 2: longest carbon chain ene .

Naming side chains CH2 CH3 CH2 C CH2 CH3 CH2 C CH3 CH3 Rule 3: attach prefix (according to # of C) 1-hexene ene .

Naming side chains CH2 CH3 CH2 C CH2 CH3 CH2 C CH3 CH3 Rule 4: Assign numbers to each carbon 1-hexene .

Naming side chains CH2 CH2 CH3 1 CH3 CH2 C 2 5 CH2 C 3 4 6 CH3 CH3 Rule 4: Assign numbers to each carbon 1-hexene .

Naming side chains CH2 ethyl CH2 CH3 1 CH3 CH2 C 2 5 CH2 C 3 4 CH3 6 CH3 methyl methyl Rule 5: Determine name for side chains 1-hexene .

Naming side chains CH2 ethyl CH2 CH3 1 CH3 CH2 C 2 5 CH2 C 3 4 CH3 6 CH3 methyl methyl Rule 6: attach name of branches 2-ethyl-4-methyl-4-methyl-1-hexene 1-hexene .

Naming side chains CH2 ethyl CH2 CH3 1 CH3 CH2 C 2 5 CH2 C 3 4 CH3 6 CH3 methyl methyl Rule 7: list alphabetically 2-ethyl-4-methyl-4-methyl-1-hexene 1-hexene .

Naming side chains CH2 ethyl CH2 CH3 1 CH3 CH2 C 2 5 CH2 C 3 4 CH3 6 CH3 methyl methyl Rule 8.9: group similar branches 2-ethyl-4-methyl-4-methyl-1-hexene 1-hexene .

4-dimethyl-1-hexene .9: group similar branches 2-ethyl-4.Naming side chains CH2 ethyl CH2 CH3 1 CH3 CH2 C 2 5 CH2 C 3 4 CH3 6 CH3 methyl methyl Rule 8.

Naming side chains • Try PE 1 on pg.6-trimethyloctane .3-dimethylheptane CH3 CH3 CH3 CH3 CH2 CH CH CH CH2 CH CH3 CH2 CH3 5-ethyl-2. 1019 (answer to a is wrong) H3C H3C CH2 CH CH3 H2C CH2 CH CH CH2 CH3 H3C CH3 3-methylhexane CH2 CH2 CH3 CH CH3 4-ethyl-2.4.

5.Naming side chains Name the structures below CH3 H3C CH CH2 CH CH3 H2C H3C H3C 3-ethyl-2-methylpentane CH3 CH3 3-ethyl-1.5trimethylcyclohexene CH3 .

4-octadiene Pg.More practice Br 4-bromo-7-methyl-2-nonene Br 2.6. 24. 24.5.14.7. 1049 # 24.15 e) .7-dimethyl-2.15 Ignore 24.5-dibromo-6-chloro-1.3-cycloheptadiene Br Cl CH3 H3C C CH3 CH2 C F CH CH CH CH3 5-fluoro-7. 24. 24.

bicarbonates. c) one H too many (should be CH3CH=CHCH2CH3). cyanides. b) is an oxide.6 .7 . d) bicarbonate.Recall.This is a straight chain molecule as all carbons are consecutive. e) carbonate 24.5 .Pg. 24.none are possible: a) one too few Hs (should be CH3CH2CH3). the exceptions to organic compounds are oxides of carbon. b) one H too many (should be CH2=CHCH2CH3). 1049 24. carbonates. .

3-dimethylcyclopentane 1.1-diethylcyclohexane 6-ethyl-5-isopropyl-7-methyl-1-octene .24.15 2.2-dimethyloctane 1.

meta.3-dimethylbenzene metadimethylbenzene H3C CH3 1.2-dimethylbenzene orthodimethylbenzene CH3 ST Ortho H3C Meta Para Benzene is very stable (does not generally undergo addition) H3C 1.4-dimethylbenzene paradimethylbenzene . para (stomp) H3C 1.H3C Aromatic nomenclature There are 2 naming methods 1) Numbering carbons 2) ortho.

3) the name of the structure. 2) the structure of your molecule.More practice • Build a molecule that can be named according to the rules that we have talked about. Give this to your teacher. • Place your model at a vacant lab station.com .chalkbored. visit www. Make it challenging. • On a scrap piece of paper write the following: 1) your station number. • Rotate through the stations. drawing the structures and determining their names. For more lessons. At the end of the class students will reveal the answer with an explanation.