15/08/2020

OUR LADY OF FATIMA UNIVERSITY

College of Pharmacy UNIT OUTCOMES
 At the end of this module, the students are expected to:

PHARMACEUTICAL AND 1. Write chemical reactions involved in some organic

compounds such as alcohols, aldehydes and ketones,
MEDICINAL ORGANIC carboxylic acids and esters.
CHEMISTRY lab 2. Differentiate tests for different organic compounds

PMOC 311

Chemical Reactions of
Organic Compounds
Exercise 1

CHECKLIST
Chemical Reactions of Organic
 Read course outcomes

 Read course guide prior to class attendance

Compounds
 Proactively participate in discussions Exercise 1
 Watch videos related to the topic

 Participate in discussion board (Canvas)

 Answer and submit course unit tasks

ALCOHOLS
 Compounds that have –OH group bonded to a saturated, alkane-like
carbon atom.
EXERCISE IA  R-OH

Classification of alcohol
(Alcohols, Aldehydes, and According to number of hydroxyl group attached to their molecule

Ketones)  monohydric, dihydric, or trihydric,

according to number of carbon atoms are bound to the carbon atom
to which the hydroxyl group is bound.
 primary, secondary, or tertiary,

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ALCOHOLS
 Monohydric alcohol
 Different kinds of carbonyl-containing products are formed,
depending on the structure of the starting alcohol and on the
reaction conditions.
 Dihydric alcohol
[O] More [O]
RCH2OH RCOH RCOOH
Primary Alcohol Aldehyde Carboxylic Acid
 Trihydric alcohol
(Formed if carefully (Formed if an excess
controlled conditions) oxidant is used)

ALCOHOLS ALCOHOLS
 Secondary alcohols (R2CHOH) are converted into ketones  Tertiary alcohols don’t normally react with oxidizing agents
(RC=OR) on treatment with oxidizing agents. because they don’t have a hydrogen on the carbon atom to
which the –OH group is bonded.
[O] [O]
RCHOHCH3 RC=OR R3COH No Reaction
Secondary Alcohol Ketone Tertiary Alcohol

TESTS FOR ALCOHOLS TESTS FOR ALCOHOLS

I. Ester Formation/ Esterification I. Ester Formation/ Esterification
It is carried out by warming a carboxylic acid with an Example 1 H+ Catalyst
alcohol in the presence of a strong acid catalyst such as CH3-CH2-CH2-C=O-OH + H-O-CH2-CH3
H2SO4. Butanoic Acid Ethanol

It is reversible and often reach equilibrium with

substantial amounts of both reactants and products CH3-CH2-CH2-C=O-CH2-CH3 + H2O
present. Ethyl butanoate Water
It is favored either by using a large excess of the alcohol or (found in pineapple oil)
by continuously removing one of the products (An
application of Le Chatelier’s Principle).

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TESTS FOR ALCOHOLS

I. Ester Formation/ Esterification
Example 2
CH3COOH + CH3CH2OH
Acetic Acid Ethyl Alcohol

CH3-C=OO-CH2CH3 + H2O
Ethyl Acetate Water
(Ethyl acetate is removed as soon as it’s formed, the production of more and
more product is forced to occur.)

TESTS FOR ALCOHOLS

Evidence of esterification
II. Test for Enol Structure
 2 layers are formed
 Top layer – ester Enols (AKA: alkenols)
 alkENe alcohOL
 A molecule which has a hydroxyl
group (OH) group directly bonded
to an alkene (C=C)

TESTS FOR ALCOHOLS ALDEHYDES AND KETONES

II. Test for Enol Structure Aldehydes and ketones are the 2 simplest families of carbonyl
 FeCl3 – traditional colorimetric test for phenol compounds.
Enols interconvert with carbonyl compounds that have an α- aldehydes
hydrogen, like ketones and aldehydes. The compound Aroma of cinnamon, vanilla, or almond are natural flavors and
is deprotonated on one side and protonated on another side, aromas from.
whereas a single bond and a double bond are exchanged. This is
called keto-enol tautomerism. Ketones
jasmone from jasmine flower
(+) – purple iron complex muscone from the male musk deer

Keto-enol tautomerism vital to the complex formulas of expensive perfumes

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PROPERTIES OF ALDEHYDES PROPERTIES OF ALDEHYDES

AND KETONES AND KETONES
moderately polar compound  state
they have higher boiling point than alkanes with similar MW.  Other simple RCHO and RCOR – liquid
 no hydrogen atoms bonded to oxygen or nitrogen, their  >12 C – solid
molecules don’t form hydrogen bond with each other  Solubility
compounds with similar MW  RCHO and RCOR soluble in common organic solvents
a. alkane - lowest boiling  <5 C soluble in water
b. alcohol - the highest boiling
 Ketone - dissolve both polar and non-polar compounds
c. aldehydes and ketones fall in between
 ↑ # carbons - become more alkane-like and less water-
soluble

PROPERTIES OF ALDEHYDES
AND KETONES TESTS FOR ALDEHYDES AND KETONES
 Flammability
I. Oxidation
 lower-boiling aldehydes and ketones - flammable  Alcohols can be oxidized to aldehydes or ketones , and
 Toxicity aldehydes can be further oxidized to carboxylic acids.
 Simple ketone - generally low toxicity  In aldehyde oxidation, the hydrogen bonded to the
 simple aldehydes (esp. formaldehyde) – toxic carbonyl carbon is replaced by an –OH group.
 Biochemistry  Ketones, because they don’t have this hydrogen, do not
 simplest sugars called monosaccharides contain either an react with oxidizing agents (except with those strong
aldehyde group or ketone group enough to destroy the molecules).

TESTS FOR ALDEHYDES AND KETONES TESTS FOR ALDEHYDES AND KETONES
I. Oxidation I.Oxidation
Oxidizing Agent  Among the mild oxidizing agents that cause the conversion from
RCHO RCOOR aldehyde to carboxylic acid, one is oxygen in the air. To prevent
oxidation, aldehydes are often stored under nitrogen gas.
Aldehyde Carboxylic Acid
 Because ketones can not be oxidized, treatment with a mild
oxidizing agent can be used as a test to distinguish between
Oxidizing Agent aldehyde and ketones. Tollen’s reagent is the most visually
RCOR No Rxn appealing oxidizing agent for aldehydes. Treatment of an aldehyde
with this reagent rapidly yields the carboxylic acid anion and
Ketone metallic silver producing a shiny mirror.

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TESTS FOR ALDEHYDES AND KETONES TESTS FOR ALDEHYDES AND KETONES
I. Oxidation I. Oxidation
Tollen’s Test Tollen’s Test
 contains the diamminesilver(I) ion, [Ag(NH3)2]+ NH3 , H20
RCHO + Ag(NH3)2+ RCOO- +
Aldehyde (Tollen’s Reagent)
ketone No change in the colourless solution.
NH4 + Ag+
The colourless solution produces a grey Silver Mirror
aldehyde precipitate of silver, or a silver mirror on the
test tube.

TESTS FOR ALDEHYDES AND KETONES TESTS FOR ALDEHYDES AND KETONES
I. Oxidation I. Oxidation
 Benedict’s reagent
RCHO + Cu2+ RCOO- + Cu2O
 contains copper(II) ions
complexed with citrate ions in Blue in sol’n Brick Red solid
sodium carbonate solution
 The reagent solution contains the blue
copper (II) ion that is reduced to give a ketone No change in the colourless solution.
precipitate of a red copper (I) oxide in the
reaction with an aldehyde sugars The blue solution produces a dark red
aldehyde
precipitate of copper(I) oxide.

TESTS FOR ALDEHYDES AND KETONES TESTS FOR ALDEHYDES AND KETONES
III. Formaldehyde Milk Test IV. Resin Formation
 + FeCl3
 Formalin is used to preserve milk for a
long time

 (+) test for formalin – violet or purple

at the junction Acetaldehyde + NaOH Acetaldehyde + NaOH + H2O

ORANGE YELLOW
An aldehyde resin is formed when heated with strong NaOH
sol’n.

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CARBOXYLIC ACIDS
Esters and amides are derivatives of carboxylic acids.

EXERCISE IB Carboxylic acids are easily converted to esters and

amides, and the esters and amides are easily converted
back to the carboxylic acids.
Carboxylic Acids and
Esters)

TESTS FOR CARBOXYLIC ACIDS

I. Ester Formation
Methanol + salicylic acid 
CH3C=OOH + CH3CH2OH
Acetic Acid Ethanol methyl salicylate

CH3C=OOCH2CH3 + H-OH Oil of wintergreen

Ethyl Acetate Water
(+) nail polish
An ester can be converted back to carboxylic acids
remover, paint or
by such reactions.
glue odor, plastic
balloon like odor

TESTS FOR CARBOXYLIC ACIDS

II. Effect of Oxidizing Agents consist of a
 Carboxylic acids are relatively resistant to oxidation, however,
carboxylic acid
some acids like alpha-hydroxy acids (AHAs)substituted
like glycolicwith a
acid, lactic acid, citric acid, mandelic acid may be oxidized.
hydroxyl group on Glycolic acid
the adjacent carbon

[O] CH3C=OH + CO2 + H2O

KMnO4
2-Hydroxypropanoic Acid
(Lactic Acid)
citric acid lactic acid

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ESTERS TESTS FOR ESTERS

When the –OH of the carboxyl group is converted to the – I. Hydrolysis
OR of an ester group (-COOR), the ability of the  In hydrolysis, a bond or bonds are broken and the H- and –
molecules to form hydrogen bond with each other is lost. OH of water add to the atoms that had been in the broken
Simple esters are therefore lower boiling than the acids bond. Esters and amides undergo hydrolysis to give back
from which they are derived. carboxylic acids plus alcohols or amides in reaction that
follow the carbonyl-group substitution pattern.
Acetic Acid ; Methyl ester ; Ethyl ester
bp 118 °C bp 57 °C bp 77 °C

TESTS FOR ESTERS TESTS FOR ESTERS

I. Hydrolysis I. Hydrolysis
 Both acids and bases can cause ester hydrolysis. Acid-catalyzed  Ester hydrolysis by reaction with a base such as
hydrolysis is the reverse of esterification. NaOH or KOH is known as SAPONIFICATION.
H2SO4 The product of saponification is a carboxylate anion
Ethyl benzoate + H-OH Benzoic Acid + Ethanol rather than a free carboxylic acid.

Methyl butanoate + NaOH(Aq)

Sodium butanoate + Methanol

TESTS FOR ESTERS TESTS FOR ESTERS

I. Hydrolysis II. Ammonolysis
ASA + water  salicylic acid  It is the reaction of an ester with aqueous or alcoholic
ammonia to form an amide.

+ H2O  Ethyl acetate + alc NH3  amide

(+) purple color

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Answers to the Questions Answers to the Questions

 Organic compounds are those that contain carbon atom  Functional groups are atoms or group of atoms that
except for cyanides, carbonates, bicarbonates including CO2 determine the characteristic chemical properties of the
and CO. They usually come from living organisms. They are molecules to which it is attached.
easily decomposed by heat and lack water solubility.  Examples are –OH, C=O, and others.

Answers to the Questions Answers to the Questions

 Combinatorial synthesis
ORGANIC COMPOUND FUNCTIONAL GROUP  chemical library used for preparing a large number of chemical
Alcohol -OH compounds.
 Its advantages are to be able to synthesize, purify, chemically
Aldehydes CHO analyze, and biologically test all the structures in the library
using synthetic methods.
Ketones C=O

Carboxylic Acids COOH

Esters COO

 Prepare for an Online quiz.

End of discussion