naming alkenes and alkynes

advertisement

- Alkenes / Dienes

- Alkynes

Alkenes

 The Alkenes form another homologous hydrocarbon series

 Each member contains one double covalent bond between two C atoms.

So alkenes are said to be unsaturated .

Only 3 atoms joined to each C, not 4

 General formula = C n

H

2n

What was the general formula for the Alkanes?

Saturated vs Unsaturated

Saturation vs. Unsaturation

 Simply put, a saturated hydrocarbon has no double bonds between the Carbon atoms (ex. alkanes)

H

H

H

C

H

C

H

H

C

H

H

C

H

H

CH

3

CH  Unsaturated has one or more double or triple bonds between carbons

(alkenes, alkynes)

H

3

C

C

C

CH

3

(CH

2

)

2

CH

3

CH

CH

3

CH

3

Physical properties of the Alkenes

-Very similar to the alkanes

Insoluble in water

- very soluble in organic solvents

- Less dense than water

B.P. and M.P increase with increasing carbon

As with alkanes B.P rises about 20-30 C per carbon

- Hexane b.p. 69 C ; 1-Hexene b.p. 63.5 C

- Heptane b.p. 98 C ; 1-Heptene b.p. 93 C

Naming Alkenes

 Names are derived from the name of the alkane chain with the same number of C atoms.

 Replace the –ane ending of the alkane name with –ene.

1 st member is C

2

H

4

, ethene.

H H

C=C

H H

Alkene Homologous Series

(C1-C2 double bond)

 Ethene

 Propene

 1-Butene

 1-Pentene

 1-Hexene

 1-Heptene

 1-Octene

 1-Nonene

 1-Decene

C=C

C-C=C

C-C-C=C

C-C-C-C=C

C-C-C-C-C=C

C-C-C-C-C-C=C

C-C-C-C-C-C-C=C

C-C-C-C-C-C-C-C=C

C-C-C-C-C-C-C-C-C=C

Naming Alkenes

 Location of double bond is specified by numbering C atoms in backbone. Give bond the lowest possible number.

1-butene (not 4)

H H H

C=C–C–C–H

H H H H

C

4

H

8

CH

2

CHCH

2

CH

3

2-butene

H H H H

H–C–C=C–C–H

H H

C

4

H

8

CH

3

CHCHCH

3

Structural Formula

Chemical formula

Condensed

Structural formula

Naming Alkenes

 Once double bond is numbered specify substituents alphabetically by number

 Use di, tri and tetra for multiple substituents of the same group

2,3-dimethyl-1-butene

C=C–C–C

C C

Structural Formula

(w/o the H)

C

6

H

12

Chemical formula

CH

2

C(CH

3

)CH(CH

3

)CH

3

Condensed

Structural formula

Problems:

 Draw the following alkenes:

2-Butene

2 –methylpropene

4 –Methyl–2-pentene

3,3-Dimethyl-1-butene

Name this Compound:

4-ethyl-5-methyl-4-octene

Dienes

 Alkenes = 1 double bond

 Dienes have 2 double bonds

Example: 1,3 – penta diene c=c-c=c-c

Not 2,4-pentadiene

End in -diene

Location still denoted by numbers

Substituents are named first

Determine which way to number the C backbone by assigning the lowest possible

[Numbers are separated by commas and the #’s are

Separated from the name by a dash number to one of the double bonds Double bonds must all be in the backbone.

Name this compound:

C=C-C-C-C=C-C

C

5-methyl-1,5-heptadiene

Draw 2-methyl-1,3-heptadiene:

C=C-C=C-C-C-C

C

Alkynes

Homologous series of unsaturated hydrocarbons that contain one triple bond.

Each member contains one triple carbon-carbon bond.

Alkynes are unsaturated.

 General formula = C n

H

2n-2

Alkyne Homologous Series

(C1-C2 triple bond)

 Ethyne

 Propyne

 1-Butyne

 1-Pentyne

 1-Hexyne

 1-Heptyne

 1-Octyne

 1-Nonyne

 1-Decyne

C C

C-C C

C-C-C C

C-C-C-C C

C-C-C-C-C C

C-C-C-C-C-C C

C-C-C-C-C-C-C C

C-C-C-C-C-C-C-C C

C-C-C-C-C-C-C-C-C C

Ethene

(Common name)

A common use of one of the alkynes:

The Acetylene torch

Hydrocarbon Table

Notice that each

Of the hydrocarbon

Families differs

From the next

By 2 hydrogen

Alkanes share 1pr e -

Alkenes share 2pr e -

Alkynes share 3pr e -

Can you explain how

The above comments

Are related?

Naming Alkynes

 Use the corresponding name from the alkane series and change the –ane to –yne.

 If necessary, number the carbon atom at which the triple bond occurs with the lowest number.

 Use the same naming process you used for naming Alkenes

Structural Chemical Name Condensed

Formula Formula Structural formula

H–C

C–H C

2

H

2 ethyne CHCH

H

H–C

C–C–H

H

C

3

H

4 propyne CHCCH

3

H H

H–C

C–C–C–H

H H

C

4

H

6

1-butyne CHCCH

2

CH

3

H H

H–C–C

C–C–H

H H

C

4

H

6

2-butyne CH

3

CCCH

3

Can you name this compound?

3-ethyl-1-pentyne

Download