UNIT 2: ALKANES, ALKENES AND ALKYNES

PART 2: ALKENES & ALKYNES

A “functional group” is a segment of an organic molecule that has unique physical and chemical properties. The
simplest type of functional group is a pi bond, or a pair of delocalized electrons. Like alkanes, alkenes and alkynes
contain only hydrogen and carbon. However, alkenes and alkynes are unsaturated, or do not contain the maximum
number of hydrogens possible due to the presence of double (alkene) and triple (alkyne) bonds.

1. MOLECULAR FORMULA AND NAMING OF ALKENES:

a. Each molecule below is an alkene. Write the molecular formula for each molecule in the space provided.

__________________ _________________ ________________________

propene (propylene) 2-butene (but-2-ene) 2-pentene pent-2-ene

(2-butylene)

b. Study each molecular formula that you wrote. Write a generic formula for alkenes.

c. Use the formula you found above to try to predict the molecular formula of an alkene with 7 carbon atoms:

d. The name for each of the molecules is given below the diagrams. Notice that the “ene” suffix replaces the “ane” that
was used for alkanes. Why do you think the number 2 is included in the name for 2-pentene and 2-butene? Why isn’t
included for propene?

NOTE: The names “2-pentene” and “pent-2-ene” are both IUPAC and commonly used today. Ethylene and butylene
are named in the “common naming system”, but are not IUPAC names. You need to be familiar with this form, but the
correct IUPAC names are propene and ethene.
2. NAMING ALKENES:
The steps for naming alkenes are given below.

 1. Find the longest continuous carbon chain that contains the double bond, and number from the end nearer
the double bond.
 2. Write the alkane name corresponding to the number of carbons, changing the –ane to –ene.
 3. Identify by number the lower-numbered carbon atom containing the double bond, followed by a hyphen
directly before the alkene name.
 4. If substituent groups are present, they should precede the name of the alkene in the usual way.

CH3
H3C

EXAMPLE: Name the following molecule: H3C CH3

CH3
5 6
H3C
4 3

H3C CH3
2 1

STEPS 1 & 2 : hexene STEP 3: 2-hexene STEP 4: 4-ethyl-5-methyl-2-hexene

hex-2-ene 4-ethyl-5-methyl-hex-2-ene

PRACTICE: Name the following molecules:

CH3
CH3 CH3
H3C

CH3 H3C CH2

3. NAMING POLYUNSATURATED ALKENES:

A polyunsaturated alkene has more than one double bond. The molecule below is a diene. To name a diene;
 List the lower numbered carbons containing the double bonds, separated by a comma.
 After the alkane name, -di- is used to signify 2 double bonds, followed by –ene.
4. MOLECULAR FORMULAS AND NAMING FOR ALKYNES: CnH2n-2
Alkynes are unsaturated hydrocarbons that contain a triple bond. To name alkynes, follow the same process you used
for naming alkenes except substitute the suffix –yne.

TRY: Name the molecules below. Use the prefix chloro- to indicate the presence of a chlorine atom. Then check your
answers:

H3C CH3 H3C Cl

H3C
CH b. CH3 c. H3C CH
a.

Answers: 1-butyne; 4-methyl-2-pentyne; 3-chloro-4-methyl-1-pentyne

but-1-yne; 4-methyl-pent-2-yne; 3-chloro-4-methyl-pent-1-yne

5. CYCLIC ALKANES, ALKENES & ALKYNES

Cycloalkanes, cycloalkenes and cycloalkynes have ring structures. The prefix “cyclo” is used in the name. Numbering
begins at the multiple bond and moves in the direction toward the nearest branch, the goal being to assign the lowest
numbers possible to the branch. All other naming rules are followed.

EXAMPLES:
CH3 CH3
2
3 4
1
CH3
4 5 CH3
3 CH3
5 3
6 5 4
2 2 6
1
Cl CH3 1
Br 3-ethyl-5-methylcyclohexyne
5-bromo-3-ethylcyclohexene 1-chloro-2,3,4-trimethylcyclopentane

1. Name the following molecules:

CH3

CH3

H3C H3C CH3

2. Write the molecular formula for each molecule. How does it compare with a noncyclic molecule
containing the same number of carbon atoms?
COMMON BRANCH NAMES: ISO-, TERT- & SEC-

Number of C Atoms
Line Drawing Name
in group
Three carbon branch coming off
3 isopropyl of a chain; attached at the middle
carbon
Four carbon branch coming off of
4 isobutyl a chain, attached at the second
carbon
Same as iso-

4 sec-butyl

Four carbons coming off of a

4 tert-butyl chain, in a “methyl propyl”
arrangement
5-carbon branch coming off of a
5 isopentyl chain, attached at the second
carbon
Same as iso-

5 sec-pentyl

Examples:

4-isopropyl nonane secbutyl cyclopentane

CH3

CH3

4-tertbutyl-cyclohexene TRY: 3-tertbutyl -4-propyl-2-octene

LOTS OF PRACTICE & CONDENSED FORMULAS: Complete the charts below. Leave the condensed formula column
blank. We will work on it together.:

NAME STRUCTURAL DIAGRAM CONDENSED FORMULA

4,4 dimethyl-2-pentene

3-methyl-4-propyl-1-
heptene

3-isopropyl cyclo-octyne

4-ethyl-2-hexyne

H3C CH3

H3C CH3

H3C
CH3
CH3
H3C

H3C Br

CH3
ALKENES/ALKYNES – HOMEWORK 1 NAME:
DATE:

1. Name each of the alkenes/alkynes below.

H3C CH3
H3C

H3C CH3
H3C Br

CH3 CH3 H3C CH3

a. b. H3C c.

4,4 dimethyl 2 hexene 4-secbutyl-2-octyne 2-bromo-3-methyl-2-pentene

CH3
F
H3C CH3
H3C CH3

d. CH3 e. CH3 f. CH3

2,4-dimethyl-2-pentene 4-ethyl-2-fluoro(2,4) hexadiene 4-propyl cyclohexyne

3. Draw and name each molecule below based on its condensed formula:

a. CH2CHCH2CH(CH3)2 b. (CH3)3CCCCH2CH2CH2Cl

H3C CH3
H3C

H2C CH3

CH3 Cl
4-methylpent-1-ene 7-chloro-2,2-dimethylhept-3-yne
4. Draw the molecules listed below:

a. 2,3 dichloro-3-heptene b. 3-hexene

Cl
H3C
H3C
Cl
CH3 CH3

5. Complete the chart:

CONDENSED FORMULA STRUCTURAL FORMULA NAME

H3C 2-methyl-3-hexene
CH3CH2CHCHCH(CH3)2
CH3
H3C
(3E)-2-methylhex-3-ene
Cl
CHC(CH2)5CH2Cl

HC
8-chlorooct-1-yne
CH3 7,7-dimethyl-(1,5) octadiene
(CH3)3CCHCH(CH2)2CHCH2 H3C
CH3

CH2