Chemistry 11

Organic Chemistry
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Book 3
Name:_____________________ Block:________

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Functional Group Overview
 Functional Groups
Earlier in this chapter, you learned about organic compounds containing carbon and hydrogen atoms. The number of isomers
possible for large hydrocarbons is enormous. Now imagine how many more isomers would be possible if we included atoms of
oxygen, nitrogen, sulphur, or other elements!

In Books 1 & 2, you learned about the structures of alkenes, alkynes, and aromatic hydrocarbons, such as benzene. Groups of
organic compounds like these are called ___________________________________groups.
A functional group is an atom, group of atoms, or organization of bonds in an organic molecule that react in a characteristic
manner.
Organic compounds with the same functional group _______________ in a ___________________manner

Functional groups are identified by the placement of certain _____________________in a molecule.

NEW SHORTHAND:

Chemists use a shorthand to represent _________________and _________________ atoms that are not part of the functional
group itself.
We use the symbol __________to represent the hydrocarbon fragment of the organic molecule __________________________
in the functional group.
______________(called “r prime”) may be used for a _________________ hydrocarbon fragment in the same molecule.
Cl Figure 8.2.1 Examples of alkyl halides
Alkyl Halides: R-X (where X = F, Cl, I, or Br)
Organic compounds containing ____________________ are called
________________________.
They are named using the same rules you learned before, except that the
halogen atom is named as a __________group.
It is treated the same way as an __________group was in branched
alkanes, alkenes and alkynes. (a)______________________________________
The ____________________to use for each element are:
Cl Br

F = _________ Cl = __________ Br = __________ I = i__________ CH CH

CH3 CH2 CH3

(b) _________________________________________

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Alcohols: R-OH
Organic compounds containing a __________________________________–OH) group attached to a carbon atom are
called ___________________________
Do not confuse a hydroxyl group with a hydroxide ion.
Compounds with a hydroxide ion are bases and are ionic.
Alcohols are ______________________________________compounds that do not readily release the –OH group.

1. The parent chain must contain an atom ______________________to the –OH group.
____________________________the carbon atoms in the parent chain such that the –OH group is given the
_______________________number.

2. The name of the parent chain ends with “____________” instead of “–e.”

3. Name and identify positions of the ________________________as usual.

Study the examples shown (right).

Note that the number indicating the

position of the -OH group is not used if
the chain is shorter than 3 carbons.

Why is that?

Also you see that the -OH group is not

included in the names of cyclic alcohols
either.

Why not?

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 O Ethers
R R΄ ____________________are organic compounds in which__________hydrocarbon fragments are
attached by an _______________________atom.

Table 8.2.2 Examples of Ethers and Their Applications

Ether Name Application Structure

Methoxymethane aerosol spray propellant O
(commonly called H3C CH3
dimethyl ether)
Ethoxyethane early anesthetic
H3C O CH3
(commonly called CH2 CH2
diethyl ether)
Methoxybenzene anise (licorice) flavoring OCH3
(commonly called
methylphenyl ether)
 O Aldehyde
R C H An aldehyde is an organic compound containing a ___________________ at the END of a carbon chain.
A carbonyl group is a ____________ atom ___________________ bonded to an ________________atom.
Aldehydes are used to produce dyes and organic acids. You may be familiar with formaldehyde, which is
used as a biological preservative. Almond extract and some perfumes contain benzaldehyde.

O
H C
H H
(a) methanal (commonly called formaldehyde) (b) benzaldehyde
Figure 8.2.2 Examples of aldehydes
 O Ketone
C A ketone is an organic compound also containing a ___________________group, but unlike an aldehyde,
R R΄ the carbonyl group of a ketone is _____________________________________________________of the
carbon chain.
Nail polish remover is a ketone commonly called ________________. Ketones are used as solvents and to
make polymers and pharmaceuticals. A polymer is a very large molecule that is produced by linking
together many smaller molecules.

O Would it be possible for a ketone to have a

O
name: "3-methyl-1-hexanone" ?
C H3C C ____________________________
H3C CH3 CH2 CH3

(a) propanone (commonly (b) 2-butanone (commonly

called acetone) called ethylmethylketone)

Figure 8.2.3 Examples of ketones

 O Carboxylic Acid
C
A carboxylic acid is an organic compound containing a ___________________________(–________) group.
These are sometimes called ___________________________and are commonly found as food preservatives.
R OH
White vinegar is a 5% solution of ethanoic acid, commonly called acetic acid.
Methanoic acid (commonly called formic acid) is the compound responsible for the sting of bee or red ant
bites.
Carboxylic acids usually have unpleasant odours.
Figure 8.2.4 Examples of carboxylic acids

O O
CH3 C H C
O H OH
(a) ethanoic acid (b) methanoic acid
(commonly called acetic acid) (commonly called formic acid)

a) _____________________________ d)_____________________________

b) _____________________________ e)_____________________________

c) _____________________________ f)_____________________________
 O Ester
C An ester is an organic compound in which a –_____________– group connects _____ other hydrocarbon
R OR΄ fragments. Many esters have strong _______________odors and are used in perfumes and flavorings.
DNA and some plastics and explosives contain ester groups.

CH3 CH3CH2CH2
Figure 8.2.5 Examples of esters C O C O
CH3CH2CH2CH2CH2CH2CH2CH2O CH3CH2O
(a) octyl ethanoate (orange flavouring) (b) ethyl butanoate (pineapple flavouring)
 Amines: R-NH2 or R-NH-R’ or as in the diagram to the left
R N R΄
Amines are organic compounds containing only ____________bonds and ______________________
R΄
΄ atoms attached to a carbon atom. Amines are used to produce dyes and drugs. For example,
chlorpheniramine is used as an antihistamine. Ephedrine and phenylephrine are decongestants.
 O Amides
R΄ Organic compounds containing a nitrogen atom bonded to a carbonyl group are called amides.
C ΄
R N Amides are found in plastics, rubber, inks, and cosmetics. Amides are also used to make nylon and
Kevlar. The pain killer acetaminophen is an amide. An amide group links amino acids together in
R΄ the peptide chains that make up proteins. You do not need to know how to name amides. Figure
8.2.7 shows two examples of amides.

O O
(a) ethanamide (ethylamide) CH3C (b) butanamide CH3 CH2 CH2 C
NH2 NH2
Figure 8.2.7 Examples of amides
 Table 8.2.3 summarizes what you have learned about the functional groups described
Functional Group in this booklet.
Summary Table 8.2.3 Functional groups

Functional Group Classification of Organic Compound

H H alkene
C C

C C alkyne
H H aromatic hydrocarbon
C C

H C C

C C
H H
X alkyl halide
C

OH alcohol
C

ether
C O C

O aldehyde
C H
O ketone
C
O carboxylic acid
C OH
O ester
C O C

NH2 amine
C

O amide
C NH2
Activity: Recognizing Functional Groups
Question
Can you classify an organic compound according to its functional group?
Background
The reactivity of an organic compound depends largely on the presence of its functional group. You can classify
organic compounds by their functional group by carefully examining which groups of atoms are present on
a molecule. You should be able to recognize the following types of functional groups in the following organic
compounds: alkane, alkene, alkyne, cycloalkane, aromatic, alkyl halide, alcohol, ether, amine, amide, aldehyde,
ketone, carboxylic acid, and ester.
Procedure
1. Work with a partner.
2. Copy the following structure diagrams onto a piece of paper.

1. CH3 2. Cl Cl
H3C
C O CH CH2 CH3
O

CH3

3. HC C CH3 4. CH3
H
C C CH3
O
CH3

5. CH3 CH CH2 OH 6. CH3

CH3 N
CH3 CH2 CH2 CH3

7. CH3 CH2 CH2 H 8. CH3

C C CH2 CH2
CH3 CH2 CH3 CH3 O C CH3

CH3

9. O 10. CH2 CH2

CH3 H3C C CH3
CH3 CH2 C N
H O

Continued on next page

3. Cut the paper into 10 squares and place each square face down on the table.

4. Take turns with your partner. Turn over one piece of paper, and state which functional groups are represented.
Some examples may include more that one functional group. If your partner agrees, you get to keep that piece
of paper. If your partner disagrees, place that piece of paper to the side.

Results and Discussion

1. Once you have completed all 10 squares, count how many questions you answered correctly. ______________

2. For questions where you disagreed, re-examine the question and try to come to an agreement about the
functional group. If you cannot agree, ask a nearby pair of students.

3. You know how to name some of these compounds. List the names below of as many as you can and compare
your answers to those of a nearby pair of students.

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