Module 1 - Nomenclature of Organic Compounds Lab 1

CHEM 36: FUNDAMENTALS OF ORGANIC CHEMISTRY
MODULE 1: NOMENCLATURE OF ORGANIC COMPOUNDS (LAB 1)

2ND SEMESTER | S.Y. 2021-2022 TRANSCRIBED BY: KATE LINDSAY MONTESCLAROS
LECTURER: MRS. DAWN ABATAYO
Nomenclature of Organic Compounds

❖ Some organic compounds are known and easily
remembered by their common names such as
acetone, acetic acid, formaldehyde, ether, isopropyl
alcohol, and many others. As one encounters more
and more organic compounds however,
memorizing their common names becomes a
tedious job.
➢ This burden is minimized through a
systematic way of naming as provided by the
International Union of Pure and Applied
Chemistry (IUPAC).
HYDROCARBONS
❖ These are organic compounds containing only
carbon and hydrogen atoms in their formulas.
❖ All other organic compounds are considered as
derivatives of the hydrocarbons as their formulas
contain other units called functional groups
attached to the parent hydrocarbon skeleton. 2. The parent chain is named using:
❖ A generic root (Table 1.1) which indicates
NAMING
the number of C atoms in the parent chain;
❖ Generally, the name of an organic compound
❖ An ending or suffix (Table 1.2) which
consists of two main parts:
indicates the class of hydrocarbon
1. Parent chain
compounds.
2. Substituent(s) or branching groups
Table 1.1 Generic roots
RULES FOR NAMING HYDROCARBONS (IUPAC SYSTEM)
Number of C Atom Generic Root
1. Select the longest continuous chain of carbon (C) 1 meth-
atoms. This is the parent chain and will serve as
the framework on which the various substituent 2 eth-
groups are attached. 3 prop-
EXAMPLE: 4 but-
5 pent-
6 hex-
7 hept-
8 oct-
9 non-
10 dec-
Table 1.2 Suffixes for hydrocarbons EXAMPLE:
Class of General Suffix Example

hydrocarbon Formula
Compounds
Alkane – all CnH(2n+2) -ane CH3 – CH3
bonds are single; Ethane
saturated 4. (a) All groups not included in the parent chain
Alkene – with at CnH2n -ene CH2=CHCH3 are considered as substituents or branches.
least one double Propene ➢ The substituents containing carbon atoms
bond; attached to the parent chain are named by
unsaturated replacing the ending -ane of the
Alkyne – with at CnH(2n-2) -yne CHC―CH3 corresponding alkane by -yl becoming an alkyl
least one triple Propyne group.
bond;
➢ Examples of alkyl groups which are used as
unsaturated
substituents are shown in Table 1.3.
3. Number the parent chain beginning at that end

which gives the lowest possible number to the
following in the given order of priority:
❖ double bond
❖ triple bond
❖ the substituent(s), in the absence of multiple
bonds. Other alkyl groups:
EXAMPLE:
❖ The position of unsaturation or multiple bonds must

be indicated before the name of the parent chain. A
dash is used to separate a number from a word.
Hence, the name of the compound above is 3- ❖ NOTE: Italicized prefixes such as sec- and tert- are
heptene, not 5-heptene. ignored when alphabetizing except when they are
compared with each other. tert-butyl precedes
isobutyl, and sec-butyl precedes tertbutyl.
➢ The prefix iso- is not hyphenated and is
considered part of the alkyl-group name for
alphabetizing purposes, but the hyphenated
prefixes sec- and tert- are not considered part
❖ Note that the position of the unsaturation shall of the name. Thus, isopropyl and isobutyl are
listed alphabetically as i, but sec-butyl and
precede the name of the parent chain like the
tert-butyl are listed as b.
example above. If both the double and triple bonds
are found in the parent chain, the double bond gets
❖ Substituents groups containing double bonds are:
higher priority in numbering (lower number) and its
suffix is indicated before that of the triple bond.
(b) The substituents are assigned numbers ❖ IUPAC name: 4-Ethyl-6-isopropyl-2-
corresponding to their position in the chain. methylnonane
➢ not 6-ethyl-4-isopropyl-8-methylnonane
➢ Number each C atom on the longest chain in the
direction that gives the smaller numbers for the EXAMPLE:
locations of all substituents (number the parent
chain such that the combination of the number-
designations gives the lowest sum)
➢ In naming, the number comes before the name
of the substituent(s), followed by the name of
the parent chain. The names are written as one ❖ IUPAC name: 6-Ethyl-3,4-dimethyloctane
word. Join the prefix (if there is any) to the name ➢ not 3-Ethyl-5,6-dimethyloctane
of the substituent, and name of the parent chain.
(f) When the substituent is a halogen, the following
prefixes are used:
Table 1.4 The halide Substituents
Halogen Name
-F Fluoro
-Cl Chloro
-Br Bromo
-I iodo
❖ IUPAC name: 4-Ethyloctane
(c) The following are the rules for punctuations:
➢ use a dash to separate a number from a word

➢ use a comma to separate numbers
(d) When there are identical substituents, position

numbers are applied for each and the prefixes, di-, tri-, ❖ IUPAC name: 2-Chloro-3-ethylhexane
tetra-, etc. are used.
(g) When a substituent is attached to a hydrocarbon
containing a multiple bond, numbering should start at
that end which gives the lowest possible number to the
multiple bonds.
❖ IUPAC name: 2,2,4,5-Tetramethylheptane
(e) When there are different substituents, they are

mentioned in alphabetical order (disregarding the
prefix). The number may be omitted when the
substituent is on Carbon-1.
❖ The longest chain chosen for the root name must (h) If more than one double bond is present the
include both carbon atoms of the double bond. compound is named as a diene, triene or equivalent
If the double bond is in the center of the chain, prefix indicating the number of double bonds and each
the nearest substituent rule is used to determine double bond is assigned a locator number.
the end where numbering starts
SELF-REVIEW QUIZ SELF-REVIEW QUIZ

1.
5. (a) Hydrocarbons can also form rings. Such

compounds are called alicyclic compounds and
❖ IUPAC name: ______________________ are named by adding the prefix cyclo- to the
name of the parent chain.
2.
❖ IUPAC name: ______________________
3.
❖ IUPAC name: ______________________
4.
(b) When the ring contains fewer carbon atoms than an

alkyl group attached to it, the compound is named as an
❖ IUPAC name: ______________________ alkane, and the ring is treated as a cycloalkyl substituent.
(c) In cycloalkenes the double bond carbons are assigned
ring locations #1 and #2. Which of the two is #1 may be
Step 4: Attach the correct number of H atoms to each
determined by the nearest substituent rule.
carbon
SELF-REVIEW QUIZ
1. 2-chloro-3-methylpentane
STRUCTURE WRITING
1. Identify the parent chain from the name
2. 7-amino-5-fluoro-4-methyl-2-nonyne
2. Set up the carbon chain. Assign numbers
consistent with the rules.
3. The name preceding the parent name describes
the substituent and its position in the parent
chain. Attach the substituents to the chain as
indicated by the numbers.
4. Supply the necessary number of H atoms to each
carbon consistent with the covalency of the
atom. Each carbon atom must have four bonds
5. Zigzag structure
EXAMPLE: 2,3,4,5-tetramethylhexane ❖ Another way of representing organic molecules
Step 1: Identify the parent chain – hexane is by means of zigzag structures. These are drawn
using zigzag lines to represent the C―C bonds.
Step 2: Set up the carbon chain and number. ➢ The C and H atoms are not shown as well as
bonds to H.
❖ Zigzag structures are the most convenient
representations for long open-chain structures
since they save time and space in writing
Step 3: Attach substituents as indicated by the numbers.
structural formulas for these compounds.
❖ Although C−H bonds are not shown, it is
assumed that each C is bonded to the correct
number of hydrogen atoms.
❖ The functional groups are shown in the
structures and also bonds of C to heteroatoms.
EXAMPLES:
❖ Ring compounds can be represented in a similar

manner, the C and H atoms are dispensed with,
leaving only the lines in the structural formula.
EXAMPLES:

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CHEM 36: FUNDAMENTALS OF ORGANIC CHEMISTRY

MODULE 1: NOMENCLATURE OF ORGANIC COMPOUNDS (LAB 1)

Nomenclature of Organic Compounds

Class of General Suffix Example

3. Number the parent chain beginning at that end

❖ The position of unsaturation or multiple bonds must

Table 1.4 The halide Substituents

(c) The following are the rules for punctuations:

➢ use a dash to separate a number from a word

(d) When there are identical substituents, position

❖ IUPAC name: 2,2,4,5-Tetramethylheptane

(e) When there are different substituents, they are

SELF-REVIEW QUIZ SELF-REVIEW QUIZ

5. (a) Hydrocarbons can also form rings. Such

❖ IUPAC name: ______________________

❖ IUPAC name: ______________________

(b) When the ring contains fewer carbon atoms than an

❖ Ring compounds can be represented in a similar

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