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Organic
Nomenclature and
Formula Writing
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Unit
Organic
Nomenclature and
Formula Writing
Organic Nomencl
Index
· Explain
· Carbon and its Bonds 06
· Organic Chemistry 06
· Organic Molecules 06
· Naming Organic Compounds 07
· Types of Formula 07
· Writing Formulas and Naming Organic Compounds 08
· Simple Hydrocarbons 08
· Saturated and Unsaturated Hydrocarbons 08
· Alkanes 08
· Alkenes 09
· Alkynes 09
· Branched-Chain Alkanes 10
· Halogenated Hydrocarbons 10
· Oxygenated Compounds 11
· Alcohols 11
· Ethers 12
· Carboxylic Acids 12
· Esters 13
· Aldehydes 13
· Ketones 14
· Nitrogenated Hydrocarbons 14
· Amines 14
· Amides 15
· Exercises 16
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lature and Formula Writing
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Explain
Types of covalent bonds between Organic chemistry studies the majority of substances containing
two carbon atoms. carbon and their properties.
Organic Molecules
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Alkanes Alkenes Alkynes
Tables
Halogens Alcohols Ethers
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Outline Writing Formulas and Naming Organic Compounds
To identify a compound unequivocally, we need to use its structural or
condensed formula. The molecular formula, by comparison, is not al-
ways exclusive to a single compound.
Given the huge variety of existing organic molecules, a system was de-
veloped to allow compounds to be named unequivocally from a struc-
tural or condensed formula, and vice versa.
Simple Hydrocarbons
Outline Saturated and Unsaturated Hydrocarbons
1.
Count each carbon atom in the parent chain.
2.
Use the prefix corresponding to the number of carbon atoms.
3.
Place the suffix -ane at the end of the name.
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Gallery
Alkenes
Alkenes are unsaturated hydrocarbons which contain at least
one carbon-to-carbon double bond.
Alkynes
Alkynes are unsaturated hydrocarbons which contain at least
one carbon-to-carbon triple bond.
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If the triple bond is found in the only possible location within the mol-
ecule, its position does not need to be indicated.
Gallery If more than one triple bond is present, write out the number of the first
carbon of each triple bond, using commas to separate numbers and
making sure to use the lowest-possible set of numbers. Then, add the in-
fix -di-, -tri-, and so on.
Branched-Chain Alkanes
Branched-chain alkanes are alkanes with chains of carbon atoms
laid out as side branches (substituent groups) of the parent chain.
Halogenated Hydrocarbons
When hydrocarbons bond to one or more halogen atoms—
namely fluorine, chlorine, bromide, or iodine— they are called
halogenated hydrocarbons.
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To name halogenated hydrocarbons, the following IUPAC rules are used:
1.
Number the carbon atoms in the parent chain, beginning with the
end carbon closest to a halogen.
2.
If necessary, write the number of the carbon atom in the parent chain Gallery
to which the halogen is attached. Use a hyphen to separate numbers
and words.
3.
Write the name of the halogen with the prefixes fluoro-, chloro-,
bromo-, or iodo-, preceded by that number indicating the substituent.
4.
Write the name of the hydrocarbon the halogen is attached to.
If the molecule has different halogens attached to the same parent
chain, place their names in alphabetical order. If the same halogen oc-
curs more than once, write the number of the carbon atoms to which
they are attached in between commas, using the infix -di-, -tri-, and so
on, as applicable.
Oxygenated Compounds
Alcohols
Alcohols are organic compounds containing at least one hy-
droxyl functional group (–OH) forming a single bond with a car-
bon atom.
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Ethers
Ethers are organic compounds in which two carbon atoms are
bonded to an oxygen atom.
Carboxylic Acids
Carboxylic acids are compounds whose chain ends with a car-
boxyl group (—COOH).
Gallery 1.
Count the carbon atoms in the chain, including the carbon of the
carboxyl group.
2.
Add the word acid at the end.
3.
Change the -e ending of the name of the hydrocarbon which has
the same number of carbon atoms to the suffix -oic.
If both ends of the chain have a carboxyl group, do not drop the -e
from the name of the hydrocarbon and place the infix -di- before
the -oic ending.
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Esters
Esters are carboxylic acids in which the hydrogen atom of the
carboxyl group has been replaced with another chain of carbon
atoms.
This way, the esters have two chains: one attached to the carbon of
the carboxylic group and the other attached to the oxygen.
To name esters, the following IUPAC rules are used:
1.
Count the carbon atoms in the two chains attached to the car-
boxyl group.
2.
Write the prefix corresponding to the number of carbon atoms in Gallery
the chain attached to the oxygen of the carboxyl group.
3.
Add the suffix -yl.
4.
As for the other chain, write the name of the hydrocarbon with the
same number of carbon atoms, but replace the -e ending with the
suffix -oate.
5.
Put the two names together, since esters are named with two words.
Aldehydes
Aldehydes are compounds in which at least one carbonyl
group is located at the end of a carbon chain (—CHO).
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Ketones
Ketones are compounds in which at least one carbonyl group;
(—CO—) is located within the carbon chain rather than at the end.
Nitrogenated Hydrocarbons
Amines
Amines are compounds containing a nitrogen atom attached
to the chain of carbon atoms. At most, the nitrogen can be at-
tached to three chains of carbon atoms.
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4.
Write the number of the carbon atom which the nitrogen atom is
attached to, using hyphens to separate numbers from words.
5.
Place the suffix -amine at the end of the name. Gallery
If the amine has two branch chains, write their names in alphabeti-
cal order and use hyphens to separate them. If the chains are identi-
cal, write in N,N- and use the infix -di-.
Amides
Amides are compounds which have an amide group (—CONH2)
at the end of the chain. In this functional group, the carbon atom
and the oxygen atom are bonded by a double bond.
If both ends of the chain have an amide group, keep the final -e of the
name of the hydrocarbon and use the infix -di- before the -amide ending. Gallery
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EXERCISES
Organic Molecules
..........
.......... ..........
..........
.......... ..........
2. Functional Groups
Identify the functional groups: [alkane / alkene / alkyne / halogen / alcohol / ether / aldehyde / ketone /
carboxyl acid / ester / amine / amide].
Types of Formula
3. Formula Types
Classify the following into molecular, condensed, or structural formulas:
A. B. C. D. E.
F. G. H. I.
4. Saturated or Unsaturated?
Indicate whether the following formulas correspond to saturated or unsaturated compounds.
Use the expression to find the molecular formula of the compound to determine whether it is a saturated or
an unsaturated hydrocarbon.
1. CH4: .......... 2. C3H8: .......... 3. C2H2: .......... 4. C10H22: .......... 5. C4H8: .......... 6. C5H8: ..........
7. C6H10: .......... 8. C20H34: .......... 9. C8H18: .......... 10. C20H42: .......... 11. C4H10: ..........
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EXERCISES
5. Multiple Bonds 4H8: .......... H atoms
C
a. Indicate how many hydrogen atoms are still C20H34: .......... H atoms
needed for the following unsaturated hydrocar-
C2H2: .......... H atoms
bons to become saturated.
C5H8: .......... H atoms
To find out, use the expression of the molecular formu-
C6H10: .......... H atoms
la of saturated hydrocarbons.
Alkanes
6. Naming Alkanes
Name the following alkanes:
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EXERCISES
9. The Smallest Combination Alkynes
a. Number the carbon atoms in both directions.
12. Naming Alkynes
Name A Name the following alkynes: In molecules with more
than one triple bond, the prefix indicating the number
of carbons must end in -a. For example, write hexa-
.......... .......... .......... .......... .......... instead of hex-.
1. CH≡CH: ..........
2. CH3−C≡C−CH2−CH2−CH2−C≡CH: ..........
Name B
3. CH3−C≡C−CH3: ..........
4. CH3−C≡C−C≡CH: ..........
5. CH≡C−C≡CH: ..........
.......... .......... .......... .......... .......... 6. CH≡C−C≡C−C≡CH: .........
1. CH2=CH–CH3: ..........
2. CH3−CH=C=CH2: .......... Compound 1.
3. CH2=CH−CH2−CH=C=CH2: ..........
4. CH2=C=CH2: ..........
5. CH2=CH2: ..........
Compound 2.
6. CH3−CH2−CH=CH2: .........
Compound 4.
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EXERCISES
Compound 5.
Compound 6. Compound 6.
Compound 8.
Compound 4. Compound 1.
Compound 5.
Compound 2.
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EXERCISES
Compound 3.
Compound 3. Compound 4.
Compound 4.
Compound 5.
Compound 6.
Compound 5.
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EXERCISES
24. Two Molecules, One Formula
Despite having different physical and chemical
properties, some compounds share the same
chemical formula. Compound 3.
This means that, despite having the same propor-
tion of elements, the atoms forming the molecules
of both compounds bond differently.
Compound 4.
When two (or more) molecules have the
same molecular formula but different struc-
tural and condensed formulas, we call them
isomers.
Compound 1. Compound 2.
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EXERCISES
Esters
Compound 1. Compound 2.
Compound 2. Compound 3.
Compound 3. Compound 4.
Compound 4.
Compound 5.
Compound 5. Compound 6.
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EXERCISES
Compound 5.
Compound 2.
Compound 6.
Compound 3.
Compound 7.
Compound 4.
Compound 8.
Compound 5.
34. Writing the Formulas for Oxygenated Hy-
drocarbons
Use the interactive editing tool in the digital version.
Compound 6. a. Write the formula for acetic acid.
b. Write the formula for formaldehyde.
32. Writing the Formulas for Ketones
c. Write the formula for ethane-1,1-diol.
Use the interactive editing tool in the digital version.
d. Write the formula for butanedione.
a. Write the formula for pentan-3-one.
e. Write the formula for pentyl butanoate.
b. Write the formula for pentanetrione.
c. Write the formula for hexan-2-one. 35. Isomers
The composition of a given molecule corresponds
d. Write the formula for hexane-2,5-dione.
to the molecular formula C3H6O2.
e. Write the formula for hexan-3-one. Which of the following compounds are isomers of
this molecule?
33. Naming Oxygenated Hydrocarbons
Name the following compounds.
Compound 1. Compound 1.
Compound 2.
Compound 2.
Compound 3.
Compound 4.
Compound 3.
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EXERCISES
Compound 4.
Compound 4.
Compound 5.
Compound 5.
Compound 6.
Compound 6.
Compound 7.
Compound 7. Compound 8.
Amides
Compound 2.
Compound 1.
Compound 3.
Compound 2.
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EXERCISES
Compound 5.
Compound 3.
Compound 6.
Compound 4.
Compound 7.
Compound 5.
Compound 8.
Compound 6.
Compound 12.
Compound 1.
41. Writing the Formulas for Organic Com-
pounds
Use the interactive editing tool in the digital version.
Compound 2. a. Write the formula for N,N-dimethylbutan-1-amine.
b. Write the formula for methylbutane.
c. Write the formula for methyl formate.
d. Write the formula for pentanedioic acid.
Compound 3. e. Write the formula for pentane.
f. Write the formula for ethoxyhexane.
g. Write the formula for butanone.
h. Write the formula for ethylene.
i. Write the formula for hexanamide.
Compound 4.
j. Write the formula for ethanol.
k. Write the formula for butanal.
l. Write the formula for butadiyne.
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NOTES
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Organic Nomenclature and Formula Writing
Related Units:
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