NOMENCLATURE OF HYDROCARBONS

Hydrocarbons are organic compounds that are composed solely of carbon and hydrogen atoms. They
are nonpolar and neutral in nature. They are classified according to type of bonds between the carbon atoms as
summarized in Table 1 below.

Table 1. Classes of Hydrocarbons

Gen.
Class Bonding Description
Formula
Alkane -C-C- CnH2n+2 Saturated hydrocarbon (aliphatic)
Alkene -C=C- CnH2n Unsaturated hydrocarbon (olefinic)
Alkyne -C≡C- CnH2n-2 Unsaturated hydrocarbon

A. Saturated Hydrocarbons: Alkanes and Cycloalkanes

The number of carbon atoms determines the name of a hydrocarbon chain as summarized in Table 2
below.

Table 2. Root Name for Carbon Chains

No. of C No. of C
Root Name Root Name
atoms atoms

1 Meth- 11 Undec-
2 Eth- 12 Dodec-
3 Prop- 13 Trideca-
4 But- 14 Tetradeca-
5 Pent- 15 Pentadeca-
6 Hex- 16 Hexadeca-
7 Hept- 17 Heptadeca-
8 Oct- 18 Octadeca-
9 Non- 19 Nonadeca-
10 Dec- 20 Eicos-

In naming hydrocarbons, the rules set by the International Union of Pure and Applied Chemistry (IUPAC)
is applied:
1. Identify the parent chain which is the longest continuous carbon chain. The rest of the attached groups are
called as substituents. If in case there are two possible parent chains, the parent is the one with a larger
number of substituents.
2. Number the parent chain starting from the end of the chain nearest the first substituent.
3. Name the substituents as alkyl (e.g. methyl, ethyl, etc.) chain and indicate their number or position of
attachment to the parent chain.
4. For substituents that occur at least twice, use the prefix di-, tri-, tetra-, penta-, etc. to indicate their number.
5. List the substituents in alphabetical order then name the parent chain. Take note that prefixes di-, tri- etc.
do not affect alphabetical order!
6. Halogen substituents are named as fluoro- (F-), chloro-l (Cl-), bromo (Br-) and iodo (I-). Special alkyl
substituents that have special names include the following:

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 isopropyl tert-butyl

Sample Exercise 1: Name the given alkane.

3-ethyl

6-isopropyl
2 4 6
1 3 5

Br 7
2-bromo 9
8 10

2-bromo-3-ethyl-6-isopropyldecane

Practice Exercise 1: Draw the structure of 6-tert-butyl-5-chloro-2,4-dimethylnonane

A cycloalkane is a saturated hydrocarbon that has carbon atoms in a ring. Its general formula is C nH2n
which make it a functional isomer of an equivalent alkene. The same rule for naming is applied with the
addition of the prefix cyclo- to the parent chain which is included in alphabetical ordering. For geometric
isomers, the prefix cis- or trans- is added at the beginning of the name. When the cylcoalkane is attached to a
longer acyclic parent chain, then it is named as a cycloalkyl substituent.

Sample Exercise 2: Name the given cycloalkane.

4-ethyl 3
4 2 Cl 2-chloro

cis- configuration
5
6
1 Cl 1-chloro

cis-1,2-dichloro-4-ethylcyclohexane

Practice Exercise 2: Draw the structure of trans-3-cyclopropyl-4,5-diethyloctane.

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B. Unsaturated Hydrocarbons: Alkenes and Alkynes

Alkenes are named as –ene to indicate the presence of double bond. The same rule as in alkane is
followed but the double bond is given priority in numbering. If there are multiple numbers of double bonds,
appropriate prefix before –ene is added to indicate the number of double bonds. Cycloakene are named with the
prefix cyclo- on the parent ring. For disubstituted alkene, the prefix cis- or trans- is added at the beginning to
indicate the geometric isomerism.

Sample Exercise 3: Name the given alkene.

4-methyl
1 5 7 7-bromo

2
3
4 6
Br

4-methyl

7-bromo-4,4-dimethyl-1,5-heptadiene

Practice Exercise 3: Draw the structure of cis-4-iodo-1,2-dimethyl-1,4-cyclohexadiene

The E,Z designation is used in determining the geometric isomerism of tri- and tetrasubstituted
alkenes. In this scheme, the alkene is subdivided into left and right sides across the double bond. The two
groups attached to the double bond at each side are assigned a high or low priority according to higher atomic
number (i.e. Br > Cl > F > O > N > C > H). If the high priority groups are at the same side, then it is designated as
a Z isomer (German “zusammen”, meaning together). Otherwise if they are opposite one another, it is
designated as an E isomer (German “entgegen”, meaning opposite).

Sample Exercise 4: Name the given alkene.

imaginary division across double bond

high pr iority Br high pr iority

3-bromo
7 5 3 1
6 4 2

low priority low priority

4-methyl

Since the high priority groups are located on the same side it is a Z isomer: Z-3-bromo-4-methyl-3-heptene.

Practice Exercise 4: Draw the structure of E-3,5-difluoro-2-pentene.

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 Alkynes are named as –yne to indicate the presence of triple bond. The same basic rule is followed
when naming alkyne. When both double and triple bonds are present, the compound is named as an enyne. The
numbering starts from the end nearest a multiple bond. However, when a choice is possible the double bond is
given the priority than the triple bond.

Sample Exercise 5: Name the given unsaturated hydrocarbon.

cis- configuration Cl 5-chloro

2 3
5 6 7 8
1 4

4-ethyl

cis-4-ethyl-5-chloro-2-octen-6-yne

Practice Exercise 5: Draw the structure of all trans-3-isopropyl-4,6,8-dodecatrien-1-yne.

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 Enabling Assessment 8.1

NOMENCLATURE OF HYDROCARBONS

NAME: __________________________________________________ SCORE: ____________

SECTION:___________ LABORATORY INSTRUCTOR:________________________________________

A. Name the following hydrocarbons (20 pts)

1. 6.

Cl

2. 7. Cl

Br

3. 8.

4. 9.
C H3
Cl Cl Cl

C H3

5. 10.

Br

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 B. Draw the structure of the following hydrocarbons. (20 pts)

1. 3-ethyl-4-(2-bromopropyl)-dodecane 6. Z-4-bromo-3-ethyl-1,4-heptadiene

2. trans-5-bromo-4-chloro-1-methyl-1,4- 7. trans-, cis-1,2,5,6-tetramethylcyclooctane

cyclohexadiene

3. 2-cyclopentyl-6-decaen-3-yne 8. E-2-cycohexyl-3-methyl-2,5-octadiene

4. 1-(2-propenyl)-cyclopentene 9. 3-ethyl-4-isopropyl-1-hepten-6-yne

5. 5. all cis-4,7,11-trimethyl-2,5,8,11-tridecatetraene 10. 4,6-dichloro-5-methyl-2-(1-methylethenyl)-

cyclohexene

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 EXPERIMENT #5: REACTIONS OF HYDROCARBONS

The reactions of saturated hydrocarbons are different from that of unsaturated ones. Generally,
unsaturated hydrocarbons are more reactive than saturated counterpart. Addition of strong oxidative reagent like
Bayer’s reagent (basic potassium permanganate) leads to the formation of alcohol for alkenes and carboxylic
acids for alkynes. Tollen’s reagent is a weak oxidizing agent composed of ammoniacal silver nitrate. It reacts
with terminal alkynes to form silver alkylides. Halogenation is the addition of halide substituents like bromine. This
occurs via different mechanisms and extent with different hydrocarbons.

Objectives
In this experiment, you will be able to distinguish hydrocarbons based on their characteristic reactions.
Using this knowledge, you will understand how to identify unknown hydrocarbon samples. Lastly, you will be able
to generate acetylene, an economically useful alkyne, from a simple reaction.

Materials and Reagent

Hexane Bromine in CCl4 Screw-capped test tubes
D-Limonene Bayer’s reagent Separatory funnel
Calcium carbide Distilled water Distilling flask
Unknown hydrocarbon 1 Tollen’s reagent Iron ring and clamp
Unknown hydrocarbon 2 Pasteur pipettes Rubber tubing and pinchcock

Procedures

PRECAUTIONS: Hydrocarbons are combustible compound. Generation of acetylene is a highly exothermic

process. Avoid direct skin contact and inhalation of vapour of hydrocarbons. Tollen’s reagent has an explosive
tendency when it forms alkylide precipitates. Dilute with copious amount of water and dispose of it immediately!

1. Place 5 drops of hexane, D-limonene, unknown hydrocarbon 1, and unknown hydrocarbon 2 on separate
dry test tubes. Prepare new set of samples for each of the chemical test below:
a. Bayer’s test – add 5 drops of Bayer’s reagent to each sample. Shake and then observe.
b. Bromination (with light) – add 5 drops of bromine. Shake and then observe.
c. Bromination (without light) – wrap the test tube with paper, add 5 drops of bromine and immediately
place the sample in a dark place for 2 minutes. Observe afterwards.
d. Tollen’s test – add 5 drops of Tollen’s reagent. Shake and then observe.
2. Prepare the set-up for acetylene generation as in Figure 1 [one set-up will suffice for the whole class].
Add the chemicals as listed in #1 a-d to four separate dry screw-capped test tubes [one for each group].
3. Add small increments of water to calcium carbide at a time to initiate the formation of acetylene. Collect
acetylene into the test tubes by inserting the end of the rubber tubing and then opening the pinchcock.
When enough acetylene is collected, cap the tubes immediately and observe any ensuing reaction.
4. From the results of the tests, identify whether your unknown sample is an alkane, alkene, or alkyne.
5. Write the pertinent general equations involved in each reaction.

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 Figure 1. Acetylene Generation Set-up

EXPERIMENT #3: REACTIONS OF HYDROCARBONS

DATA SHEET
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 EXPERIMENT #3: REACTIONS OF HYDROCARBONS

NAME:________________________________________________________________ SCORE:_________

SECTION:______ DATE PERFORMED:____________ INSTRUCTOR:_____________________________

SCHEMATIC DIAGRAM (10 pts)

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 A. Chemical Test Results (20pts)

Bayer’s Test Br2 Test (light) Br2 Test (dark) Tollen’s Test
Visible + result
SAMPLES
Hexane
D-Limonene
Acetylene
Unknown 1
Unknown 2
Legend: ++ → fast reaction; + → slow reaction; - → no reaction

Identities of Unknown Hydrocarbons

Sample 1:___________________________
Sample 2:___________________________

B. Pertinent General Reactions (15 pts)

(1) Bayer’s oxidation:

(2) Bromination (light):

(3) Bromination (dark):

(4) Tollen’s Test:

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 C. Follow-up Questions and Applications (15 pts)

1. Which of the above chemical tests can be used to distinguish the following? (3 pts)
a. Alkane from alkene

b. Alkane from alkyne

c. Alkene from alkyne

2. Why are unsaturated hydrocarbons more reactive than saturated ones? (3 pts)

3. What is the difference between the mechanism of bromination of saturated and unsaturated hydrocarbons?
(3pts)

4. What is the chemical equation involved in the generation of acetylene? (3 pts)

5. What are the economic uses of acetylene? (3pts)

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