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NH4CNO → (NH2)2CO
Objectives:
At the end of this module, you should be able to:
1. enumerate and explain the reasons for over a million of organic compounds
2. differentiate organic compounds from inorganic compounds
3. familiarize with the qualitative test of different elements in an organic
compound and the quantitative value
Lesson 1: Why there are so Many Organic Compounds
Carbon is included in the compounds of all living things and also in the materials
that are use daily like clothes, soaps, perfumes, foods, flavors, plastics and a lot more.
The occurrence of a large number of organic compounds is due to carbon’s combining
capacity such as the following:
3. It combines with other elements like halogens (ex. Cl, Br, F, I).
Examples: CH3Cl or H
H–C–Cl
H
5. It exists as isomers.
There are two general types of isomers:
1. Structural isomers - have the same molecular formula but have
different structural formula
Example:
Ethyl Alcohol Dimethyl Alcohol
H H H H
H–C–C–O–H H–C–O–C–H
H H H H
Molecular Formula: C2H6 Molecular Formula: C2H6
State: Liquid State: Gas
Boiling Point: 78.5°C Boiling Point: -23.7°C
2. Stereoisomers - same molecular and structural formula but differ from
each other in their three-dimensional structure.
Example: Structural Formula of Valine
H Mirror
CH3–CH–CH–C–COOH CH3CHCH3 CH3CHCH3
CH3 NH2
H COOH HOOC H
H2N NH2
Molecular Formula: C5O2H
Stereoisomers can have different three dimensional structures
which are mirror images of each other.
Note: To be considered isomers, it should have the same molecular
formula (actual number of atoms present in the compound) but
different in their structures. More isomerism will be discussed
later.
After analyzing the lecture, now I know that you are ready for the SAQ.
SAQ 1-1-1:
Let us see if you understand the overview of organic chemistry and you know the
reasons for having a large number of organic compounds by matching Column A with
Column B. Write the letter only on the space before each number.
Column A Column B
ASAQ 1-1-1:
1. H 2. E 3. J 4. A 5. I 6. C 7. F 8. K 9. B 10. D
2.1 Organic compounds are flammable, volatile and unstable as compared to inorganic
compounds. They char at moderately high temperature.
2.2 Ionic compounds are crystalline solids at room temperature. Electrostatic forces
hold the ions in a crystal together while molecular compounds are covalently
bonded due to sharing of electrons. Intermolecular forces of attraction holds the
molecules in a crystal structure such as dipole interaction, Van der Waals forces of
attraction and hydrogen bonding.
2.3 Inorganic compounds contain ions, and in aqueous solutions, conducts electricity
and are classified as electrolytes. Organic compounds are covalently bonded and
do not ionize in water. Thus, most of the organic compounds in water do not
conduct electric current and are classified as non-electrolytes.
Examples: NaCl in H2O - conducts electricity - electrolyte
Sugar in H2O - do not conduct electricity - non-electrolyte
2.4 In general, ionic compounds involving ionic bonds have higher boiling points than
covalent compounds. This is because the amount of energy required to separate
ions that are electrostatically attracted is much higher than that required to separate
molecules in covalent compounds like organic compounds.
2.5 The solubility of a compound in a given solvent depends on the type of the
interaction between the compounds and the solvent. One rule given regarding
solubility is that “like dissolves like”.
2.5.1 Most organic compounds are soluble in organic solvent.
Examples:
Ethanol is soluble in diethyl ether
Hydrocarbons and other nonpolar organic compounds (equal sharing
of electrons) like naphthalene (moth balls) are soluble in kerosene -
C12H28 - C16H34
2.5.2 Most ionic and polar covalent compounds are soluble in water (H–O–H), a
polar solvent (polar solvent - unequal sharing of electrons)
Examples: NaCl and H2O - soluble
CH3CH2OH and H2O - soluble
The attraction of ions, like Na+ and Cl-, with dipoles (α+ and α-), with a
molecule like water (H–O–H),-
α α
+
provides energy to the ions from the crystal
lattice and is called ion-dipole interaction making Na + and Cl- soluble in water.
2.5.3 Polar organic compounds are water soluble only if they are small and contain
nitrogen or oxygen atoms that can form hydrogen bonds with water.
Examples:
stearic acid which is composed of nonpolar C–C and C–H (17) and
C–O and OH is insoluble in water
glucose (C6H12O6) is soluble in water because it has many C–O and
OH that forms hydrogen bonding with water
Act 1-2-1
A. Fill up the table below with the required information.
Criteria Inorganic Organic
>4C-16C =
a. Physical State <16C =
b. Combustibility
c. Melting Point/Boiling
Point
Criteria Inorganic Organic
d. Solubility in Water
e. Solubility in Organic
Solvent
f. Conductivity
g. Structure of Solid
h. Bonding
i. Volatility
1. Ignition Test
a. Flammability
Compound Flammability
a. Ethyl Alcohol
b. Water
b. Charring
Compound Charring
a. Sugar
b. Salt
2. Solubility
Compound Solubility Reasons
3. Conductivity
Electrolyte/ Light or Without
Compound Reasons
Non-electrolyte Light
a. NaCl
Solution
b. Sugar
Solution
c. Ethyl
Alcohol
Solution
(Submit this activity on _______________ through GC, e-mail or FB until 5:00 pm.)
After answering your activity by yourself, you may now go to the SAQ (Self-
Assessment Question).
SAQ 1-2-2:
ASAQ 1-2-2:
1. Non-electrolye
2. Electrolyte
3. Non-electrolye
4. Insoluble
5. Soluble
6. Soluble
7. Ion-dipole
8. Dipole-dipole or H-bonding
9. Like dissolves like (Hexane - nonpolar; Water - polar solvent)
10. H-bonding
3.1.4 Sulfur
3.1.4.1 Sodium nitroprusside Test
Lassaigne extract (organic compound used contain S) plus
sodium nitroprusside solution produces purple coloration.
A. Fill up the table below. Consider the formula of the tested compound as your guide.
1. Ferrox Test for Oxygen
Test Compound Formula (Research) Color Change
a. acetone
b. benzene
c. ethyl alcohol
d. kerosene
2. Test Compound
Name of Test Color Change
e. monochloroacetic acid
f. albumin (egg white)
g. CO2 + lime water
B. Question
1. How will you prepare ferrox paper?
2. What is the role of CuO in the given reaction in the 3.1.1 topic?
Let’s see whether something has retained in your mind by answering the SAQ.
SAQ 1-3-3
Match Column A with Column B. Write the letter only on the space provided.
Column A Column B
_____ 1. Ferrox Test A. detects the presence of sulfur
_____ 2. CuO B. predominant elements in organic
compounds
_____ 3. Silver nitrate Test C. decompose organic compound into
inorganic
_____ 4. Sodium Fusion ions
_____ 5. Lime Water Test D. it is also known as sodium fusion extract
_____ 6. Sodium nitroprusside Test E. serves as catalyst
_____ 7. Carbon and Hydrogen F. test for oxygen
_____ 8. Lassaigne Extract G. indicates the presence of hydrogen
_____ 9. Lead acetate Test H. identify the presence of chlorine
_____ 10. Chlorine, Bromine, Iodine I. signify the formation of CO2
J. test for nitrogen
ASAQ 1-3-3
1. F 2. E 3. H 4. C 5. J 6. K 7. B 8. D 9. A 10. I
For C (CO2):
at. wt. of C
Computed Weight of C = wt. of CO2 ×
MW of CO 2
where: at. wt.= atomic weight
MW = molecular weight
computed weight of C
%C = × 100
weight of sample
or
at. wt. of C
wt. of CO 2 ×
MW of CO2
%C = × 100
weight of sample
For H (H2O):
at. wt. of H (2) balance the
Note:
Computed Weight of H = wt. of H 2 O ×
MW of H 2 O no. of atoms
computed weight of H
%H = × 100
weight of sample
or
at. wt. of H (2)
wt. of H2 O ×
MW of H2 O
%H = × 100
weight of sample
3.2.2 Halogens (Cl, Br, I)
The organic compound with halogen was heated and fused with HNO 3
in the presence of AgNO3 using Carius method to produce AgX (silver halide
such as AgCl, AgBr and AgI). The amount of halogen or percentage can be
calculated using this formula:
at. wt. of X
Computed Weight of X = wt. of AgX ×
MW of AgX
computed weight of X
%X = × 100
weight of sample
or
at. wt. of X
wt. of AgX ×
MW of AgX
%X = × 100
weight of sample
Note:
X: Br, Cl, I AgX: AgBr, AgCl, AgI
3.2.3 Sulfur
Carius method was used in the detection of sulfur. Sulfur present in an
organic compound is oxidized to H2SO4 and forms BaSO4 precipitate when
reacted with BaCl2, therefore, to determine the mass and percentage of
sulfur, use this formula:
at. wt. of S
Computed Weight of S = wt. of BaSO 4 ×
MW of BaSO 4
computed weight of S
%S = × 100
weight of sample
or
at. wt. of S
wt. of BaSO4 ×
MW of BaSO4
%S = × 100
weight of sample
3.2.4 Nitrogen
Nitrogen is determined using Dumas method. This is done by heating
organic samples in high temperatures in the presence of oxygen. This leads
to the release of CO2, H2O and N2. Then, it passes through a special column
with KOH that absorbs CO2 and H2O. Another thermal conductivity tube
(nitrometer) is used to separate N2 from any residual nitrogen from any
residual CO2 and H2O and then heated with copper.
Reaction Involved:
sample + CuO → N2 + oxide of nitrogen
oxide of nitrogen + Cu → N2 + CuO
Note: If the temperature, pressure and volume are given and another volume
is unknown, use the formula for unknown volume using the combined
gas law:
P 1 V 1 P2 V 2 P1 V 1 P 1 V 1 T 2
= hence, =
T1 T2 T1 T 1 P2
For %N:
MW of N2
× V2 of N2 at STP (ml)
22,400 ml
%N = × 100
weight of sample
computed weight of N 2
%N = × 100
weight of sample
or
at. wt. of N (2)
wt. of N2 ×
MW of N2
%N = × 100
weight of sample
3.2.5 Oxygen
The percentage of oxygen can be calculated simply by subtracting the
total percentage of all the elements in the organic compound from 100 since
there is no direct way of determining the percentage of oxygen.
%O = 100 - % of other elements
Sample Problem
1. Determine the wt. of C, %C, wt. of H and %H in 19.8 g of organic sample when
heated to produce CO2 = 41.98 g, H2O = 6.45 g.
Answer:
at. wt. of C
a. wt. of C = wt. CO 2 ×
MW of CO 2
12 g/mol
= 41.98 g ×
44 g/mol
= 11.45 g
computed weight of C
b. %C = × 100
weight of sample
11.45 g
= × 100
19.8 g
= 57.82%
or
at. wt. of C
wt. of CO 2 ×
MW of CO2
%C = × 100
weight of sample
12 g/mol
41.98 g ×
44 g/mol
= × 100
19.8 g
= 57.82%
For: Hydrogen
computed weight of H
b. %H = × 100
weight of sample
0.72 g
= × 100
19.8 g
= 3.62%
or
at. wt. of H (2)
wt. of H2 O ×
MW of H2 O
%H = × 100
weight of sample
2 g/mol
6.45 g ×
15 g/mol
= × 100
19.8 g
= 3.62%
c. %O
Σ % of other elements = 57.82 + 3.62 = 61.44%
%O = 100 - Σ % of other elements
= 100 - 61.44
= 38.56%
You may now perform the given activity to see how well you understood the
lesson. To get corresponding points, show your computations by using GUESA as a
guide (Given, Unknown, Equation, Solution, Answer). You may use a calculator and a
periodic table for the atomic weights.
3. In Carius method, find the %Cl in an organic compound that weighs 0.15 g and
gives 0.12 g AgCl.
Now, try the following exercises to see how well you have grasped the lesson.
SAQ 1-3-4
1. Glucose weighing 0.1014 g was burned to produce 0.1486 g CO 2 and 0.0609 g
of H2O. Since glucose contains carbon, hydrogen and oxygen, determine the
masses of C, H and O in the sample and the percentages of these elements.
ASAQ 1-3-4
1. wt. of C = 0.4055 g
2. wt. of H = 0.0068 g 2 points each
3. %C = 39.99%
4. %H = 6.72%
5. wt. of O = 0.0540 g
%O = 3.2%
Lontoc Betty Marges and Cruz Luzviminda G. (1997) Laboratory Outline and Notebook
for Basic Organic Chemistr Makati City: Diwa Scholastic Press Inc.
Smith, Janice G. (2010), General, Organic and Biological Chemistry, New York, USA:
McGraw-Hill Co.
Solomons, Graham T.W. amd Fhryle, Craig B. (2000), Organic Chemistry. 7th Edition,
New York, USA: John Willey & Sons Inc.
Whitten, Kennet W. et al. (2007), Chemistry. 7th Edition USA: Thomson Brook/Cole Co.
Internet
amrita create (2017). Detection of Elements: Lassaigne test – Meit Olabs. Retrieved
August 1, 2020 from http://www.amrita.edu/create
Tutorial at Point (India) Ltd. (2018). Quantitative Analysis of Nitrogen by Duma Method.
Retrieved August 1, 2020 from http://www.tutorialpoint.com/videot
Activity Schedule
August 24, 2020
Welcome Activity and Course Orientation 8:00 - 10:00 am
via Google Meet
Module 1
Read Lessons 1-3
August 24 - September 9, 2020
Do SAQ 1-1-1 to 1-3-4
Submit on August 31, 2020
Act 1-2-1
up to 3:00 pm on agreed site
Submit on September 7, 2020
Act 1-3-2
up to 2:00 pm on agreed site
Submit on September 14, 2020
Act 1-3-3
up to 2:00 pm on agreed site