CHEM 31.

1
POSTLAB 3
By: June Mark E. Taedo, R.Ch.

Organic Derivatives of Water

Formed by replacing the H atom of H20 with alkyl group

which results to the formation of:

OH

OH

General Properties

Presence of
H- bonding

Presence of Hydrophobic
and Hydrophilic regions

Acidic (usually weak acids)

Alcohols
Compounds that possess a hydroxyl group and are

characterized by names ending in ol

Cholesterol

Cholecalciferol (vitamin D3)

Phenols
A special kind of alcohol
Comprised of a hydroxyl (-OH) group

attached directly to a phenyl ring

Substituted phenols are extremely common in nature
and exhibit a wide variety of properties and functions

Capsaicin

Tetrahydrocannabinol (THC)

Ethers
Common name: identify each R group; arrange them in alphabetical

order, and then add the word ether

Systematic name: choose the larger group to be the parent alkane;
name the smaller group as an alkoxy substituent

Morphine

Vitamin E

Tests Performed
Reaction with KMnO4
Tollens Test
Lucas Test
Reaction with FeCl3
Iodoform Test

Chemical Reactions
Reaction with KMnO4
Oxidation of alcohols by dilute acidic solution
Depends upon the presence of a weak C-H bond from which a pair
of electrons can be easily lost
1 and 2 alcohols are readily oxidized
3 alcohols are oxidized under drastic conditions (highly acidic or basic)
RCH2OH + KMnO4 + H+
RCHO + Mn4+ +H2O

Samples

Results

1-butanol

2-butanol

Tert-butyl alcohol

Diisopropyl ether

Phenol

Chemical Reactions
Tollens Test
Test for oxidation of compounds with aldehyde group
R

OH

+ Ag(NH3)2NO3 No Reaction
+ NaOH

OH

Samples

Results

1-butanol

2-butanol

Tert-butyl alcohol

Diisopropyl ether

Phenol

Chemical Reactions
Lucas Test
Uses anhydrous ZnCl2 in concentrated HCl
Used to differentiate 1 , 2 and 3 alcohols
Reacts via SN1 mechanism
The presence of turbid, oily solution indicates a positive result

Samples

Results

1-butanol

No reaction

2-butanol

Reacts ~5 mins

Tert-butyl alcohol

Reacts
immediately

Diisopropyl ether

No reaction

Phenol

No reaction

Chemical Reactions
Reaction with FeCl3
Positive result is indicated by formation of a violet colored product
Color appears due to a complex ion containing hexavalent iron
Phenol is an ortho-para director

OH

HO
Cl

Cl

+ FeCl3
Cl

Samples

Results

1-butanol

2-butanol

Tert-butyl alcohol

Diisopropyl ether

Phenol

Chemical Reactions
Iodoform Test
Test for terminal ketones

Samples

Results

1-butanol

2-butanol

Tert-butyl alcohol

Diisopropyl ether

Phenol

Carbonyl Compounds & Carbohydrates

Compounds containing carbonyl groups
Usually used for modifying the flavor or scent of products

GZ
*Z= R or H

O
H

Aldehydes
Carbonyl carbons are flanked by an H atom
Naming: the suffix -al indicates the presence of an

aldehyde group:
Choosing the parent chain: identify the longest chain
that includes the carbon atom of the aldehydic group

Ketones
Carbonyl carbons are flanked by two carbon atoms
Naming: the suffix -one indicates the presence of a

ketone group

Carbohydrates
Commonly referred to as sugars
Polyhydroxy aldehydes or ketones
Earliest carbohydrates to be isolated and purified were

originally considered to be hydrates of carbon

Carbohydrates
Can exist in closed form
Mutarotation
Can exist as polymer

Carbohydrates
Carbohydrates containing a hemiacetal are in equilibrium

with an acyclic aldehyde, making them reducing sugars.

Glycosides are acetals, so they are not in equilibrium with
any acyclic aldehyde, making them nonreducing sugars.

Tests Performed
Hydrolysis
Tollens test
Iodoform test
Reaction with 2,4-DNP (2,4-dinitrophenylhydrazine)
Molisch Test
Benedicts Test
Osazone test

Chemical Reactions
Hydrolysis of Di- and Polysaccharides
Disaccharides and polysaccharides are readily hydrolysed by
heating it with the presence of strong acids
OH

OH
O

O
HO

H+

Glucose + Fructose

OH
HO

HO
OH

OH

OH
HO
---O
HO

OH

O
O
OH
HO

H+

O
OH

O---

OH

~3000 Glucose monomers

Chemical Reactions
Hydrolysis of Di-

and Polysaccharides

Results for the

Hydrolysis of Diand Polysaccharides

Samples

Results

Sucrose

Starch

Cellulose

Chemical Reactions
Tollens Test
Test for oxidation of compounds with aldehyde group
O

O
H

+ Ag(NH3)2NO3 Ag + NaNO3 +
+ NaOH
+ NH3 + H2O

+ Ag(NH3)2NO3 No Reaction
+ NaOH
Samples

Results

Aldehyde

Ketone

O Na

Chemical Reactions
Iodoform Test
Test for terminal ketones
-COCH3 group will react with hypohalite (NaOX) to form
trihalogenated compound
Trihalogenated compound decomposes to give the sodium salt of
an acid and a haloform (if NaOI is used, a yellow solid is formed)

+ NaOI
CH3

+ NaOH
CI 3

+ NaOI
CI 3

++

O Na

Yellow

HCI 3

Chemical Reactions
Reaction with 2,4- DNP
Both aldehydes and ketones react with this reagent
2,4- DNP easily add to the carbonyl group
Insoluble products are formed
O

or
H

Samples

Results

Aldehyde

Ketone

Chemical Reactions
Molisch Test
Test for the presence of carbohydrates
Useful for identifying any compound which can be dehydrated to
furfural or hydroxymethyl furfural in the presence of H 2SO4
A positive reaction is indicated by appearance of a purple ring at

the interface between the acid and test layers

Sample

Results

Cyclohexanone

Glucose

Sucrose

Starch

Chemical Reactions
Benedicts Test
Test for reducing sugars
Reducing sugar: contain the carbonyl grouping; they reduce metal
oxidizing agents ; all aldoses are reducing sugars
Formation of brick-red precipitate indicates positive results
In acidic medium, oxidation of monosaccharide is faster than
disaccharides

+ Cu2+

OH-

Cu2O +

Samples

Results

Glucose

Fructose

+/-

Sucrose

Lactose

Hydrolysates

Chemical Reactions
Osazone Formation
Reducing monosaccharides and disaccharides react with
phenylhydrazine to form osazones
All reducing sugars form osazones
Microscopic examination and reference to standard osazones may
lead to an identification of reducing sugar

+ 3 C6H5NHNH2

Samples

Results

Glucose

Fructose

Sucrose

Lactose

Acyl Compound, Soap & Detergent

Acyl compounds are compounds that contains a carbonyl group

which is directly bonded to an electron-rich molecule (G)

O

Acyl compounds are usually made by using carboxylic

acids that was treated with bases to form a stable intermediate

Acyl Compound, Soap & Detergent

Hydrolysis of TAG (triacylglycerides) forms soap

Soap

Detergents

Acyl Compound, Soap & Detergent

Soaps when used

in hard water

General Properties
Relative Order
of Reactivity

Resonance
Effects

General Properties
Nucleophilic Acyl
Substitution

Acyl/Acid Halide
OH group of the carboxylic acid replaced by: halogen
Naming: Replace -ic acid with -yl chloride or -yl

bromide
acid halides and acid anhydrides are highly reactive and
are therefore not very common in nature

Acid Anhydride
Loss of water from two molecules of a carboxylic acid results in an

acid anhydride
acid halides and acid anhydrides are highly reactive and are therefore
not very common in nature
Symmetrical anhydride: if two carboxylic acid molecules are the
same
Naming: replace acid with anhydride
Mixed anhydride: two carboxylic acid molecules are different
Naming: state names of both acids in alphabetical order, followed by
anhydride

Ester
More stable and are abundant in nature as compared to

acid halide and acid anhydride

Naturally occurring esters often have pleasant odors and
contribute to the aromas of fruits and flowers:
Naming: indicate the alkyl group attached to the oxygen
atom followed by the carboxylic acid, for which the suffix
ic acid is replaced with ate

Amide
Amides are abundant in living organisms. (i.e. proteins are

comprised of repeating amide linkages)

Naming: replace the suffix ic acid or oic acid with amide

Tests Performed
Hydrolysis
Saponification
Reaction with acid
Soft water
Hard water
Emulsifying action

Chemical Reactions
Hydrolysis of Acyl Compounds
Reaction of an organic compound with water
Often catalysed by acid or base
Might involve refluxing of HCl or NaOH solution
Undergone by amides, esters and acyl chlorides
O

NH2
O

+ H-O-H

H /OH
+

+
+ H-O-H H /OH

+ H-O-H H /OH
+

Cl

Sample

Results

Acetyl chloride

Acetic anhydride

Ethyl benzoate

Benzamide

Chemical Reactions
Saponification
Process by which soap is made
From fats and oils, which contain three ester groups
Upon treatment with a strong base, (ex. NaOH) the ester

groups are hydrolyzed giving glycerol and three (3) soap

molecules

TAG
(ex. Coconut oil)

Soap

Chemical Reactions
Reaction with Aqueous Acid
+ H 2O
+ H 2O

H+

H+

Carboxylic
acid

Sample

Results

Soap

Miscible solution

Detergent

Miscible solution

Chemical Reactions
Emulsifying Action of Soaps and Detergents
Emulsion: a colloid of two or more liquids that are normally
immiscible
Both phases, dispersed and continuous, are liquids
Inherently unstable and do not tend to form spontaneously
An appropriate "surface active agent" (surfactant) can increase the

kinetic stability of an emulsion

Amines, Amino Acids & Proteins

Compounds that contain nitrogen atom directly bonded to

an alkyl group
H
H2N

C
H

O
C OH

General Properties
Properties are somewhat similar to alcohols because of

the presence of H- bonds

Low molecular weight amines have fish-like odors

Basic

General Properties

Acid-Base Properties

Peptide bonds

Amines
Derivatives of ammonia in which one or more of the protons have

been replaced with alkyl or aryl groups

Amines are abundant in nature (especially plants) in the form of
alkaloids.
Many amines also play vital roles in neurochemistry
The presence of a lone pair is responsible for most of the reactions
exhibited by amines, specifically, the lone pair can function as a base
or as a nucleophile

Amino Acids
Contains an amino group and a carboxylic acid group
The presence of two functional groups (-NH2 & -COOH)

enables amino acids to link together

Hundreds of different amino acids are observed in nature,
but only 20 amino acids are abundantly found in proteins.
Exist naturally in L form

Amino Acids
Contains acidic and basic properties
Isoelectric Point: a specific pH at which the

concentration of the zwitterionic form reaches its

maximum value

Proteins
Polymers of amino acid monomers that are coupled

together by amide linkages (peptide bonds)

Peptide:
Protein:
The order in which they are connected are important

Proteins
Generally described in terms of four levels of structures
Primary: sequence of amino acid residues
Secondary: three-dimensional configuration of localized regions
helix
pleated sheets
Tertiary: three-dimensional shape
Quaternary: structure made of two or more proteins

Proteins
May function as:
Structural proteins

Enzymes
Chymotrypsin
Trypsin
Transport proteins

Tests Performed
Preparation of diazonium
Replacement reaction of diazonium
Coupling reaction of diazonium
Ninhydrin Test
Biuret Test
Reaction with lead nitrate

Chemical Reactions
Preparation and Replacement of Diazonium Salt
NH2
O
S
HO

+ HNO2
+ H+

O
S
HO

+ H2O
+ HCl

OH
O
S
HO

+ H2SO4
+ H2O

O
S
HO
O

N N Cl
O
S
HO

N N Cl

N,N- dimethyl-paminoagobenzene
(orange)

Coupling reaction of Diazonium Salt

N N Cl
O
S
HO

+
O

N N

CH3

H3C
N

O
S
HO
O

CH3
N
H3C

Chemical Reactions
Color Reactions: reveal the presence of certain amino

acids in the protein molecule

Ninhydrin Test
Usually employed in fingerprinting
Intense purple color indicates presence of amino acids (yellow if

Proline)
O
OH
OH
O

Ninhydrin

H2N

R
Amino acid

OH

NaOH
H2O

N
O

Ruhemanns
Purple

Chemical Reactions
Results for Ninhydrin Test

Sample

Results

Casein

Yellow

Albumin

Purple

Alanine

Purple

Chemical Reactions
Biuret Test
General test for proteins
Protein reacts with copper(II) sulfate (blue)
Positive test result is indicated by the formation of a violet colored
complex
NH2

H2O
H2N
2+

Cu
NH2

H2O

H2N

Samples

Results

Casein

Albumin

Alanine

Chemical Reactions
Reaction with Lead Nitrate
Heavy metal ions precipitate proteins from their solutions by crosslinking free amino groups and carboxylate groups
NH2

NH3
O

NH3

H3N

NaOH

NH2

H2N
O

O
O

O
+
NH3

O H N+
3

Pb2+

O
NH2

O H N
2

Chemical Reactions
Reaction with Lead Nitrate
Ions commonly used for testing for the presence of proteins include
Zn2+, Fe3+, Cu2+, Sb3+, Ag1+, Hg2+, Cd2+, and Pb2+.
They cause serious damage to proteins (especially enzymes) by
denaturing them
Sample

Results

Casein

Albumin

Alanine

References

Klein, D. 2015. Organic Chemistry 2nd Edition. John Wiley and Sons, Inc.
Koffuor, G. 2012. Molischs Test- Qualitative Test in Carbohydrates. KNUST Open
Educational Resources. Kwame Nkrumah University of Science
and
Technology. Kumasi, Ghana. http://
web.knust.edu.gh/oer/pages/index.php?siteid=knustoer&page=find_materials&cou=
41
Date accessed: 20 April 2016
Lim- Sylianco C.Y. and Lorica R.G. 1962. Elementary Organic Chemistry
Laboratory Manual. University of the Philippines.
Lucas, H. J. 1930. A New Test for Distinguishing the Primary, Secondary
and
Tertiary Saturated Alcohols. Journal of the American Chemical Society 52 (2): 802
804. doi:10.1021/ja01365a053. 20 April 2016
McMurry. 2010. Organic Chemistry Edition. W.H. Freeman and Company.
Smith, JG. 2008. Organic Chemistry 3rd Edition. The McGraw- Hill Companies,
Inc.
Senese, F. 2010. What is a simple test for the presence of amino acids?.
General Chemistry Online!. http://
antoine.frostburg.edu/chem/senese/101/organic/faq/amino-acid-test.shtml 21 April
2016