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Naming Hydrocarbons (nomenclature). Handout: Hydrocarbons: IUPAC names. Drawing structures: it’s all good. 2-butene. On a test, choose a method that shows all Hs. This is called the “condensed structure”. CH 3 CH=CHCH 3.

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drawing structures it s all good
Drawing structures: it’s all good

2-butene

On a test, choose a method that shows all Hs

This is called the “condensed structure”

CH3CH=CHCH3

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

background formulas for hcs
Background: formulas for HCs
  • Alkanes= CnH2n+2, enes= CnH2n, ynes= CnH2n-2
  • Remember enes, then think of what would happen if bond was single or triple instead.
  • Provides some useful information (e.g. for compositional analysis, or to check work)
  • Cannot always tell hydrocarbon type based on numbers (e.g. propyne vs. propadiene)

Q - how many hydrogens in each of these:

6 carbon alkane

Alkene: C22H

14

44

8 (2x5 - 2 = 10 - 2)

naming common vs iupac

Formic acid

Acetone

Acetylene

Naming: common vs. IUPAC
  • Common names used in the 1800’s are still used for some compounds today:
  • 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
basic names of hydrocarbons
Basic names of hydrocarbons
  • Hydrocarbon names are based on: 1) class 2) # of C, 3) side chain type and 4) position
  • 1) name will end in -ane, -ene, or -yne
  • 2) the number of carbons is given by a “Prefix”

1 meth- 2 eth- 3 prop- 4 but- 5 pent- 6 hex- 7 hept- 8 oct- 9 non- 10 dec-

  • Actually, all end in a, but a is dropped when next to a vowel. E.g. a 6 C alkene is hexene

Q - What names would be given to these:

7C, 9C alkane

2C, 4C alkyne

1C, 3C alkene

heptane, nonane

ethyne, butyne

does not exist, propene

mnemonic for first four prefixes

Monkeys

Eat

Peeled

Bananas

Mnemonic for first four prefixes

First four prefixes

  • Meth-
  • Eth-
  • Prop-
  • But-
other prefixes
Other prefixes
  • Pent-

?

Decade

Decimal

Decathalon

  • Oct-
  • Dec-
  • Hex-, Hept-, Non-
numbering carbons

C2H4

Numbering carbons

1-pentene

Q- draw pentene

A- Where’s the bond?

We number C atoms

  • Thus, naming compounds with multiple bonds is more complex than previously indicated
  • Only if 2+ possibilities exist, are #s needed
  • Always give double bond the lowest number
  • Q - Name these

2-butene

Ethene

3-nonyne

multiple multiple bonds

CH3CH2CH2CH=C=CH2

Multiple multiple bonds

2,3-heptadiene

2,4,6-nonatriyne

  • Give 1st bond (1st point of difference) lowest #
  • include di, tri, tetra, penta, etc. before ene/yne
  • Comma between #s, hyphen between #-letter
  • You do not need to know ene + yne

2-butyne

1,2,4-pentatriene

1,2-hexadiene

cyclic structures
Cyclic structures
  • Cyclic structures are circular
  • Have “cyclo” in name
  • Benzene is not a cyclic structure
  • cyclopentane

Q- Draw these (note: carbons in a double bond should be consecutive- 1 and 2, 5 and 6, etc.):

cyclobutene 1,3-cyclopentadiene cyclopropane

naming side chains

C

H

3

H

C

C

H

3

3

C

H

3

Naming side chains
  • 2,3-dimethylpentane
  • Names are made up of: side chains, root
  • Root is the longest possible HC chain
  • Must contain multiple bonds if present
  • Add -yl to get name of side chain
  • Common side chains include:

CH3- methyl CH3CH2- ethyl

CH3CH2CH2- propyl (CH3)2CH- isopropyl

  • “iso” (branched) is not an IUPAC convention
  • Br- (bromo), Cl- (chloro), F- (fluoro), I- (iodo)
naming side chains12
Naming side chains

Example: use the rules on the bottom of handout to name the following structure

Rule 1: choose the correct ending

ene

naming side chains13
Naming side chains

Rule 2: longest carbon chain

ene

naming side chains14
Naming side chains

Rule 3: attach prefix (according to # of C)

1-hexene

ene

naming side chains15
Naming side chains

Rule 4: Assign numbers to each carbon

1-hexene

naming side chains16
Naming side chains

Rule 4: Assign numbers to each carbon

1-hexene

1-hexene

naming side chains17
Naming side chains

ethyl

methyl

methyl

Rule 5: Determine name for side chains

1-hexene

1-hexene

naming side chains18
Naming side chains

ethyl

methyl

methyl

Rule 6: attach name of branches

2-ethyl-4-methyl-4-methyl-1-hexene

1-hexene

naming side chains19
Naming side chains

ethyl

methyl

methyl

Rule 7: list alphabetically

2-ethyl-4-methyl-4-methyl-1-hexene

1-hexene

naming side chains20
Naming side chains

ethyl

methyl

methyl

Rule 8,9: group similar branches

2-ethyl-4-methyl-4-methyl-1-hexene

1-hexene

naming side chains21
Naming side chains

ethyl

methyl

methyl

Rule 8,9: group similar branches

2-ethyl-4,4-dimethyl-1-hexene

naming side chains22
Naming side chains
  • Try PE 1 on pg. 1019 (answer to a is wrong)

3-methylhexane

4-ethyl-2,3-dimethylheptane

5-ethyl-2,4,6-trimethyloctane

naming side chains23
Naming side chains

Name the structures below

3-ethyl-2-methylpentane

3-ethyl-1,5,5-trimethylcyclohexene

more practice
More practice

Pg. 1049 # 24.5, 24.6, 24.7, 24.14, 24.15

Ignore 24.15 e)

4-bromo-7-methyl-2-nonene

2,5-dibromo-6-chloro-1,3-cycloheptadiene

5-fluoro-7,7-dimethyl-2,4-octadiene

pg 1049
Pg. 1049

24.5 - Recall, the exceptions to organic compounds are oxides of carbon, carbonates, bicarbonates, cyanides.

b) is an oxide, d) bicarbonate, e) carbonate

24.6 - This is a straight chain molecule as all carbons are consecutive.

24.7 - none are possible: a) one too few Hs (should be CH3CH2CH3), b) one H too many (should be CH2=CHCH2CH3), c) one H too many (should be CH3CH=CHCH2CH3).

24 15
24.15

2,2-dimethyloctane

1,3-dimethylcyclopentane

1,1-diethylcyclohexane

6-ethyl-5-isopropyl-7-methyl-1-octene

aromatic nomenclature

Ortho

Meta

Para

Aromatic nomenclature

1,2-dimethylbenzene

orthodimethylbenzene

There are 2 naming methods

  • Numbering carbons
  • ortho, meta, para (stomp)

ST

1,3-dimethylbenzene

metadimethylbenzene

Benzene is very stable (does not generally undergo addition)

1,4-dimethylbenzene

paradimethylbenzene

more practice28
More practice
  • Build a molecule that can be named according to the rules that we have talked about. Make it challenging.
  • Place your model at a vacant lab station.
  • On a scrap piece of paper write the following: 1) your station number, 2) the structure of your molecule, 3) the name of the structure. Give this to your teacher.
  • Rotate through the stations, drawing the structures and determining their names. At the end of the class students will reveal the answer with an explanation.

For more lessons, visit www.chalkbored.com