Functional groups

Hydroxyl group: Alcohol

Prepared by: Ma. Divina Kristi A. Discar

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 There are about 10 million
known organic compounds.
Functional groups How can we possibly study
those enormous compounds?

 What is a functional group ?

 A functional group is an atom or group of atoms within a

molecule that shows a characteristic set of predictable physical
and chemical behaviors
 The same functional group in whatever organic molecule it
occurs, undergoes the same type of chemical reactions.

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 There are about 10 million
known organic compounds.
Functional groups How can we study possibly
those enormous compounds?

 A functional group is important because they are units by

which we divide organic compounds into families of
compounds

Example: (a) OH (hydroxyl) group bonded to a

tetrahedral carbon into a family called
alcohols
(b) COOH (carboxyl group) belong to a family called
carboxylic acid

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Six Common Functional groups
Family Functional Group Example Name

Alcohol OH CH3CH2OH Ethanol

Amine NH2 CH3CH2NH2 Ethylamine
Aldehyde

H CH3 H Acetaldehyde
Ketone
Acetone
CH3 CH3
Carboxylic Acid
Acetic acid

OH CH3 OH
Ester
Ethyl acetate

OR CH3 OCH2CH3
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 There are about 10 million
known organic compounds.
Functional groups How can we study possibly
those enormous compounds?

 Functional groups are sites of predictable chemical

behavior, in whatever compound it is found, undergoes the
same type of chemical reactions.
 Functional groups determine in large properties of organic
compounds.
 Functional groups serve as the units by which we classify
organic compounds into families.
 Functional groups serve as the basis for naming organic
compounds
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 There are about 10 million
known organic compounds.
Functional groups How can we study possibly
those enormous compounds?

Lesson Objective: Pattern Recognition

(a) How to recognize and identify one of these six common functional
groups when you see it
(b) How to draw structural formulas of molecules containing it

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 Alcohols
The functional group is –OH (hydroxyl) group bonded to a tetrahedral
carbon

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 Alcohols
The functional group is –OH (hydroxyl) group bonded to a tetrahedral
carbon

A. Physical Properties
B. Structure
C. Nomenclature

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A. Physical Properties of alcohols

• The most important physical properties of alcohols is polarity of their –OH groups.
• Alcohols have higher boiling points than alkanes, alkenes, and alkynes of similar molecular
weight, because alcohol molecules associate with one another in liquid state ny hydrogen
bonding. The strength of hydrogen bonding between alcohol molecules is approximately 2 to 5
kcal/mol, which means that extra energy is required to separate hydrogen-bond alcohols from
their neighbors.
• Alcohols are much more soluble in water than hydrocarbons of similar molecular weight,
because alcohol molecules interact by hydrogen bonding with water molecules
• As molecular weight increases, the water solubility of alcohols becomes more like that of
hydrocarbons of similar molecular weight. Higher-molecular-weight alcohols are much less
soluble in water, because the size of the hydrocarbon portion of their molecules (which decreases
water solubility) becomes so large relative to the size of the –OH group (which increases water
solubility).

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A. Physical Properties of alcohols
Structural formula Name Molecular weight Boiling point (OC) Solubility in water
(amu)

CH3OH methanol 32 65 Infinite

CH3CH3 Ethane 30 -89 Insoluble

CH3CH2OH Ethanol 46 78 Infinite

CH3CH2CH3 Propane 44 -42 Insoluble

CH3CH2CH2OH 1-Propanol 60 97 Infinite

CH3CH2CH2CH3 Butane 58 0 Insoluble

CH3CH2Ch2CH2OH 1-Butanol 74 117 8g/100g

CH3CH2CH2CH2CH3 pentane 72 36 Insoluble

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 -OH
B. Drawing Structural Formulas of Alcohols (Hydroxyl
group)

R H H

R C O H H C C O H
CH3CH2OH
H H
R
Functional Condensed
Group Structural
Structural
Formula
Formula
R=H
(hydrogen or An alcohol
Carbon (ethanol)
group)
*R indicates either a hydrogen or another carbon group

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B. Drawing Structural Formulas of Alcohols -OH
(Hydroxyl
group)

H H CH3

CH3 C OH CH3 C OH CH3 C OH

H
CH3 CH3

A 1O alcohol A 2O alcohol A 3O alcohol

*Alcohols are classified as primary (1O), secondary (2O), tertiary (3O), depending
on the number of carbon atoms bonded to the carbon bearing the –OH group.

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B. Drawing Structural Formulas of Alcohols

Exercise 1 (Example):

Draw Lewis structures and condensed structural formulas for the two
alcohols with the molecular formula C3H8O. Classify each as primary,
secondary or tertiary. OH

C C C C C C OH C C C

Carbon chain The two locations for the –OH group

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B. Drawing Structural Formulas of Alcohols

Strategy and Solution to Sample Problem 1:

Finally, add seven more hydrogens, giving a total of eight as shown in the
molecular formula. Show unshared electron pairs on the Lewis structures but not
on the condensed structural formulas.
H

H H H
H Lewis structures
H

H H H
H
Condensed structural
CH3CH2CH2OH CH3CHCH3 formulas

A primary alcohol (1-Propanol) A secondary alcohol (2-Propanol)

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B. Drawing Structural Formulas of Alcohols

Chemical
Connection

The secondary alcohol (2-Propanol), whose common name is

isopropyl alcohol, is the cooling, soothing component in rubbing
alcohol

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B. Drawing Structural Formulas of Alcohols
Exercise 2

Draw Lewis structures and condensed structural formulas for the four alcohols
with the molecular formulaC4H10O. Classify each alcohol as primary, secondary,
or tertiary. (Hint: First consider the connectivity of the four carbon atoms; they
can be bonded either four in a chain or three in a chain with the fourth carbon as
a branch on the middle carbon. Then consider the points at which the –OH group
can be bonded to each carbon chain.)

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C. Nomenclature of Alcohols

The IUPAC names of alcohols are derived in the same manner as those for alkenes and
alkynes, with the exception that the ending of the parent alkane is changed from –e to
–ol. The ending –ol tells us that the compound is an alcohol.

1. Select as the parent alkane the longest carbon chain that contains the –OH group
and number it from the end that gives –OH the lower number. In numbering the
parent chain, the location of the –OH group takes precedence over alkyl groups,
aryl groups, and halogens.
2. Change the ending of the parent alkane from –e to –ol and use a number to
show the location of the –OH group. For cyclic alcohols, numbering begins at the
carbon bearing the –OH group; this carbon is automatically carbon 1.
3. Name and number substituents and list them in alphabetical order.
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C. Nomenclature of Alcohols

The IUPAC names of alcohols are derived in the same manner as those for alkenes and
alkynes, with the exception that the ending of the parent alkane is changed from –e to
–ol. The ending –ol tells us that the compound is an alcohol.

4. A compound containing two hydroxyl groups is named as diol, one containing

three hydroxyl groups as a triol, and so on, the final e- in the name of the parent
alkane is retrained- for example, 1,2-ethanediol.
5. As with many organic compounds, common names for certain diols and triols have
persisted. Compounds containing a hydroxyl groups on adjacent carbons are often
referred to as glycols.

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C. Nomenclature of Alcohols

To derive common name for alcohols, name the alkyl group bonded to –OH and then
add the word “alcohol”, name the alkyl group bonded to –OH and then add the word
“alcohol”. Following are IUPAC names and, in parenthesis, common names of some
low- molecular weight alcohols:

Test: Please write

OH the line-angle
OH
OH formula and the
Ethanol Cyclohexanol
common name of 2-
1-Propanol
(Ethyl alcohol) (Propyl alcohol) (Cyclohexyl alcohol) Propanol.

*IUPAC name
*(Common name) 19
C. Nomenclature of Alcohols

EXERCISE 3 Write the IUPAC name of each alcohol.

OH
a.) OH b.) OH c.

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C. Nomenclature of Alcohols

EXERCISE 3: Write the IUPAC name of each alcohol.

OH
a.) OH b.) OH c.

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