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SAMPLE PROBLEM FORMULA OF ORGANIC COMPOUNDS

Compounds maybe represented either by a molecular formula or a structural
DIRECTIONS: Indicate the hybridization of the orbitals on each carbon. formula. A Molecular Formula indicates the atomic composition of the compound
while Structural Formula shows the arrangement of atoms and bond. Structural
formula can be alternatively drawn using any of the following types of formula:
A. B. C. D.  𝑬𝑿𝑷𝑨𝑵𝑫𝑬𝑫 𝑶𝑹 𝑪𝑶𝑴𝑷𝑳𝑬𝑻𝑬 𝑺𝑻𝑹𝑼𝑪𝑻𝑼𝑹𝑨𝑳 𝑭𝑶𝑹𝑴𝑼𝑳𝑨
- a structural formula that shows all the valences and the bonds between atoms

Ex. 𝐶 𝐻 (propane)

FORMULA OF ORGANIC COMPOUNDS FORMULA OF ORGANIC COMPOUNDS

 𝑪𝑶𝑵𝑫𝑬𝑵𝑺𝑬𝑫 𝑺𝑻𝑹𝑼𝑪𝑻𝑼𝑹𝑨𝑳 𝑭𝑶𝑹𝑴𝑼𝑳𝑨  𝑪𝑶𝑵𝑫𝑬𝑵𝑺𝑬𝑫 𝑺𝑻𝑹𝑼𝑪𝑻𝑼𝑹𝑨𝑳 𝑭𝑶𝑹𝑴𝑼𝑳𝑨
- the abbreviated or condensed forms of structural formula which shows only - the abbreviated or condensed forms of structural formula which shows only
specific bonds, other bonds are left out as implied specific bonds, other bonds are left out as implied

Ex. 𝐶 𝐻 (butane) Ex. 𝐶 𝐻 (butane)

In cases where there is branching In cases where there is branching

𝐶𝐻 𝐶𝐻
𝐶𝐻 − 𝐶𝐻 − 𝐶 −𝐶𝐻 −𝐶𝐻 − 𝐶𝐻 𝐶𝐻 𝐶𝐻 𝐶 (𝐶𝐻 ) (𝐶𝐻 ) 𝐶𝐻 𝐶𝐻 − 𝐶𝐻 − 𝐶 −𝐶𝐻 −𝐶𝐻 − 𝐶𝐻 𝐶𝐻 𝐶𝐻 𝐶 (𝐶𝐻 ) (𝐶𝐻 ) 𝐶𝐻
𝐶𝐻 𝐶𝐻
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FORMULA OF ORGANIC COMPOUNDS Exercises

 𝑩𝑶𝑵𝑫 − 𝑳𝑰𝑵𝑬 𝑺𝑻𝑹𝑼𝑪𝑻𝑼𝑹𝑬 𝑶𝑹 𝑳𝑰𝑵𝑬 − 𝑨𝑵𝑮𝑳𝑬 𝑺𝑻𝑹𝑼𝑪𝑻𝑼𝑹𝑬𝑺 DIRECTIONS: Draw the expanded structural formula, condensed structural formula, and
bond-line structure for compounds that satisfy the following molecular formulas. There is
Example: more than one possibility in each case.
𝐶𝐻 (𝐶𝐻 ) 𝐶𝐻

a. 𝐶 𝐻
b. 𝐶 𝐻 𝑂
c. 𝐶 𝐻 𝑁

SAMPLE PROBLEM CHAPTER 2: ALKANES

DIRECTIONS: Identify the functional groups in each of the following molecules.
LEARNING OBJECTIVES
At the end of the lesson, the students should be able to:

identify and draw acyclic alkanes and cycloalkanes;

identify constitutional isomers;
name alkanes using the IUPAC system of nomenclature;
predict the physical properties of alkanes;
and write equations for the complete and incomplete combustion
of alkanes
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ALKANES ALKANES AND ALKANE ISOMERS

• The carbon–carbon single bond in ethane results from σ (head-on) • Alkanes are often described as saturated hydrocarbons:
overlap of carbon s𝑝 hybrid orbitals. If we imagine joining three, hydrocarbons because they contain only carbon and hydrogen;
four, five, or even more carbon atoms by C-C single bonds, we can saturated because they have only C-C and C-H single bonds and thus
generate the large family of molecules called alkanes. contain the maximum possible number of hydrogens per carbon.
• Alkanes are also occasionally called aliphatic compounds, a name
derived from the Greek aleiphas, meaning “fat.”

AN INTRODUCTION TO IUPAC
ALKANE ISOMERS NOMENCLATURE
• Isomers are compounds that have the same • In earlier times, when relatively few pure organic chemicals were
numbers and kinds of atoms but differ in the known, new compounds were named at the whim of their discoverer.
way the atoms are arranged. It comes from the Thus, urea (𝐶𝐻 𝑁 𝑂) is a crystalline substance isolated from urine;
Greek isos + meros, meaning “made of the morphine ( 𝐶 𝐻 𝑁𝑂 ) is an analgesic (painkiller) named after
same parts.” Compounds like butane and Morpheus, the Greek god of dreams; and acetic acid, the primary
isobutane, whose atoms are connected organic constituent of vinegar, is named from the Latin word for
differently, are called constitutional isomers. vinegar, acetum.
• The potential for discovery or synthesis of great numbers of chemical
compounds showed the need for a method of systematically naming
millions of compounds.
NUMBER OF ALKANE ISOMERS
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• Early in the 20th century, the International Union of Pure and Applied NOMENCLATURE OF CONTINUOUS CHAIN,
Chemistry (IUPAC) developed the IUPAC system of nomenclature, UNBRANCHED ALKANES:
which relates names of compounds to molecular structure. For BASIS OF ORGANIC NOMENCLATURE
example, the name of a simple hydrocarbon is based on the number
of carbon in the longest continuous chain of carbons in the • Compounds containing only carbon and hydrogen, with continuous
molecules. Double bonds and triple bonds are identified, and their unbranched carbon chains and with only single bonds, are named
with Greek name for the number of carbons followed by the suffix –
locations within the longest chain are described numerically. ane. For example, a compound with a 5 carbon chain is named pent,
the Greek denoting five, followed by the suffix –ane, which indicates
that all carbon-carbon bonds are single bonds.
• Ring or cyclic hydrocarbons followed the same naming scheme except
that the prefix cyclo- is used to indicated that the chain is a ring.

• The names of some continuous-chain alkanes NOMENCLATURE OF BRANCHED-CHAIN

ALKANES

• Branched-chain alkanes are compounds in which shorter

carbon chains (alkyl groups) are attached to longer carbon
skeletons. Their names are based on the name of the longest
continuous carbon chain; If you imagine removing a hydrogen
atom from an alkane, the partial structure that remains is
called an alkyl group.
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NOMENCLATURE OF BRANCHED-CHAIN • Combining an alkyl group with any of the functional groups listed
ALKANES earlier makes it possible to generate and name many thousands of
compounds. For example:
• Alkyl groups are named by replacing the -ane ending of the parent
alkane with a -yl ending. Removal of a hydrogen atom from the
end carbon of any straight-chain alkane gives the series of
straight-chain alkyl groups

• Just as straight-chain alkyl groups are generated by removing a

hydrogen from an end carbon, branched alkyl groups are generated NAMING ALKANES
by removing a hydrogen atom from an internal carbon. Two 3-carbon
alkyl groups and four 4-carbon alkyl groups are possible.
• A chemical name typically has four parts in the IUPAC system of
nomenclature: prefix, parent, locant, and suffix. The prefix identifies
the various substituent groups in the molecule, the parent selects a
main part of the molecule and tells how many carbon atoms are in
that part, the locants give the positions of the functional groups and
substituents, and the suffix identifies the primary functional group.
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PRACTICE
• All but the most complex branched-chain alkanes can be named by
following four steps. For a very few compounds, a fifth step is needed.
STEP 1
Find the parent hydrocarbon
heptane hexane
a) Find the longest continuous chain of carbon atoms in the molecule, and nonane
use the name of that chain as the parent name. The longest chain may not
always be apparent from the manner of writing; you may have to “turn
corners.”
nonane
undecane cyclohexane

cyclohexane decane heptane

https://www.chemistrysteps.com/naming-alkanes-iupac-nomenclature-practice-problems/

b) If two different chains of equal length are present, choose the one with the STEP 2
larger number of branch points as the parent. Number the atoms in the longest chain
a) Beginning at the end nearer the first branch point, number each carbon
atom in the parent chain.

The first branch occurs at C3 in the proper system of numbering, not

at C4.
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b) If there is branching an equal distance away from both ends of the parent STEP 3
chain, begin numbering at the end nearer the second branch point. Identify and number the substituents
a) Assign a number, or locant, to each substituent to locate its point of
attachment to the parent chain.

STEP 4
b) If there are two substituents on the same carbon, give both the same Write the name as a single word
number. There must be as many numbers in the name as there are a) Use hyphens to separate the different prefixes, and use commas to
substituents. separate numbers. If two or more different substituents are present, cite
them in alphabetical order. If two or more identical substituents are present
on the parent chain, use one of the multiplier prefixes di-, tri-, tetra-, and so
forth, but don’t use these prefixes for alphabetizing. Full names for some of
the examples we have been using are as follows:
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STEP 5
• The substituent is treated as a whole and is alphabetized according to the first
Name a branched substituent as though it were itself a compound. letter of its complete name, including any numerical prefix. It is set off in
In some particularly complex cases, a fifth step is necessary. It occasionally parentheses when naming the entire molecule.
happens that a substituent on the main chain is itself branched. In the
following case, for instance, the substituent at C6 is a three-carbon chain
with a methyl group. To name the compound fully, the branched substituent
must first be named.

Number the branched substituent beginning at the point of its attachment

to the main chain, and identify it—in this case, a 2-methylpropyl group.

• For historical reasons, some of the simpler branched-chain alkyl groups also have • The common names of these simple alkyl groups are so well entrenched in the
nonsystematic, common names, as noted earlier. chemical literature that IUPAC rules make allowance for them. Thus, the following
compound is properly named either 4-(1-methylethyl)heptane or 4-
isopropylheptane. There’s no choice but to memorize these common names;
fortunately, there are only a few of them.

• When writing an alkane name, the nonhyphenated prefix iso- is considered

part of the alkyl-group name for alphabetizing purposes, but the hyphenated
and italicized prefixes sec- and tert- are not. Thus, isopropyl and isobutyl are
listed alphabetically under i, but sec-butyl and tert-butyl are listed under b.
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SAMPLE PROBLEM 1 SAMPLE PROBLEM 2

What is the IUPAC name of the following alkane? What is the IUPAC name of the following alkane?

𝐶𝐻 − 𝐶𝐻 − 𝐶𝐻

𝐶𝐻 − 𝐶𝐻 − 𝐶𝐻 −𝐶𝐻 − 𝐶𝐻 −𝐶𝐻

2,6-dimethyloctane 𝐶𝐻 𝐶𝐻 −𝐶𝐻

3-ethyl-4,5-dimethyloctane

SAMPLE PROBLEM 3 SAMPLE PROBLEM 4

What is the IUPAC name of the following alkane? What is the IUPAC name of the following alkane?
𝐶𝐻
𝐶𝐻 𝐶𝐻
𝐶𝐻 𝐶𝐻 𝐶𝐻
𝐶𝐻 − 𝐶 − 𝐶𝐻 − 𝐶𝐻 − 𝐶𝐻 − 𝐶𝐻 − 𝐶𝐻
𝐶𝐻 − 𝐶𝐻 − 𝐶𝐻 −𝐶𝐻 − 𝐶𝐻 −𝐶𝐻 − 𝐶𝐻 − 𝐶𝐻
𝐶𝐻 𝐶𝐻 − 𝐶𝐻
𝐶𝐻 𝐶𝐻 𝐶𝐻 − 𝐶𝐻 − 𝐶𝐻
5-ethyl-2,2,4-trimethylheptane
4,7-diethyl-3,3,5-trimethyldecane