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NAME:

ORGANIC CHEMISTRY LABORATORY

INTRODUCTION TO ORGANIC CHEMISTRY

LEARNING OBJECTIVES:
1. Give examples of uses of organic compounds.
2. Identify the carbon valence electrons and the hybridization of their orbitals.
3. Predict the angles of covalent bonds of carbon atoms in hydrocarbons.
4. Apply the nomenclature of simple hydrocarbons.
5. Interpret some of the important representations of hydrocarbons.
6. Give examples of functional groups of organic compounds and their reactions.

PROCEDURE:
1. Access the recorded virtual lab simulation in our Files section. You can do it individually since the
recorded virtual lab simulation can be accessed using mobile smartphones and tablets. You may use
the designated group channels if you want to have a discussion forum.
2. Do the hands-on mini experiments. Exercise extreme caution when handling the test samples. If you
have PPEs, please do wear it when doing the hands-on activities. Provide proper documentations.
3. Answer the laboratory guide questions provided. Make sure you will cite your references.

RECORDED VIRTUAL LAB SIMULATION ON ORGANIC CHEMISTRY INTRODUCTION: LEARN ABOUT ORGANIC
COMPOUNDS
Go to Files > Class Materials > Organic Chemistry Introduction – Learn About Organic Compounds

GUIDE QUESTIONS

1. What makes carbon such a unique element?

- Carbon is (1) small, (2) has 4 valence electrons, & (3) can form bonds with itself to form rings and
chains
- Being small allows carbon to fit with larger elements/molecules
- Having 4 valence electrons allows for having up to 4 bonds either with itself or other atoms
2. What is orbital hybridization? How does it affect the carbon bond angles in organic compounds?
- Orbital hybridization is the mixing of atomic orbitals to create new configurations called hybrid
orbitals.
- It can also be described as “the combination of two or more atomic orbitals to form the same
number of hybrid orbitals, each having the same shape and energy.
- Orbital shapes affect bond angles because of electron-electron repulsion. Atoms and pairs of
electrons arrange themselves in such a way as to minimize repulsion from each other (VESPR
model)
o Essentially, the atoms and their bonds in a molecule would be where the electron clouds
have the least repulsion (as far away from each other as possible)
 o
3. How do we classify organic compounds?
- We classify organic compounds in 2 ways:
o Based on carbon skeleton/structure
 Open chain/acyclic/aliphatic compounds
 Closed chain/cyclic/ring chain compounds
o Presence of functional groups
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4. What is structural isomerism?
- Structural isomerism is when two or more molecules have the same chemical/molecular formula
but the atoms are bonded differently (differ in the ways the atoms are bonded together)

- Ex.
5. What are hydrocarbons? How do we classify and name them?
- Hydrocarbons are organic compounds that are made up of only hydrogen and carbon.
- They are classified by structure:
o Aliphatic/open chain hydrocarbons can be divided into three subgroups
 Alkanes – single bond between carbon atoms
 Alkenes – double bond between carbon atoms
 Alkynes – triple bond between carbon atoms
o Aromatic hydrocarbons are closed chain hydrocarbons.
 Benzene is an example
- Hydrocarbons are named based on the amount of Cs, the type of bonds they have (single, double,
or triple), and if they are cyclic or not.
o If cyclic, start with cyclo-
o The amount of Cs of the parent chain (longest continuous chain of Cs) determine the prefix
 1 C – meth-
 2 Cs – eth-
 3 Cs – prop-
 4 Cs – but-
 5 Cs – pent-
 6 Cs – hex-
 And so on and so forth in the same style of pent- and hex-
o The type of bonds they have determine the suffix
 Single bond – -ane
 Double bond – -ene
 Triple bond – -yne
o If there is more than one double or triple bond, add the numerical position of the bond/s
(starting on the side the strongest bond (triple bond>double bond>single bond) is nearest.
o If there are branches, name said branches using the prefix and adding -yl to it, and add the
numerical position before the branch.
o Put it together by adding the branches, cyclo- if it’s a cyclic, the prefix, the number of the
double bonds (if any), the -ene (if any double bonds), the number of triple bonds (if any),
and -ene (if any triple bonds). If no triple or double bonds, end with -ane.
6. What are functional groups and hydrocarbon side groups?
- Functional groups are heteroatoms or groups of heteroatoms that are attached to a hydrocarbon.
- Hydrocarbon side groups are hydrocarbons attached to a main, parent hydrocarbon.
7. In the recorded virtual simulation, what are the different tests conducted in determining the nature
and identity of an organic compound? Explain their mechanisms.
- Bromine test (not done – just discussed a bit)
o Checks whether a solution contains unsaturated organic compounds
 Bromine reacts with double or triple bonds.


 Electrophilic addition reaction
 - Ceric ammonium nitrate test
o Tests for hydroxy (-OH) group
 Ceric ammonium nitrate reacts with an alcohol or phenol group and results in a dark
red color.


 Oxidative reaction
- Sodium bicarbonate test
o Tests for signs of a carboxylic acid group
 Sodium bicarbonate reacts with acidic compounds resulting in brisk effervescence.
The bicarbonate (HCO3-) is converted to water and gaseous CO2.


 Substitution reaction

GENERALIZATION/CONCLUSION (Answered the Learning Objectives)

Organic compounds have many uses. The Labster video used salicylic acid as an example, which is a precursor
and metabolite to the acetylsalicylic acid of aspirin. It modulates COX1 enzymatic activity thus decreasing the
making of pro-inflammatory prostaglandins, essentially decreasing inflammation.

Other organic compounds and their uses include:

Organic substance Type of organic substance Use
Glutamic acid Amino Acid Flavor enhancer
Aspartame Amino Acid Low-calorie artificial sweetener
Sucrose Disaccharide Carbohydrate Sugar
Methane carboxylic acid Acetic Acid Vinegar
Propane Hydrocarbon Fuel in domestic and industrial
applications

Carbon has 4 valence electrons in its ground state. When bonding with other atoms, carbon hybridizes: sp3 if
its single bond, sp2 if double bond, and sp if triple bond.
Carbon atoms have different bond angles given the different numbers of regions of high electron density
around the central atom. The arrangement of the regions falls into 3 types:
1. Tetrahedral
2. Trigonal planar
3. Linear

The geometry of the molecule can differ in each arrangement though.

Number of regions Arrangement of
of high electron regions of high Predicted bond Geometry of
Examples
density around electron density in angles molecule
central atom space
CH4 Tetrahedral
4 Tetrahedral 109.5° NH3 Pyramidal
H2O Bent
H2CO Trigonal planar
3 Trigonal planar 120° C2H4 Planar
SO2 Bent
CO2 Linear
2 Linear 180°
C2H2 Linear

Given a hydrocarbon, bond angles between single bonded carbons (alkanes) are 109.5° and have a tetrahedral
shape. Bond angles between double bonded carbon atoms (alkenes) are 120°, making them trigonal planar.
And bond angles between triple bonded carbon atoms (alkynes) are 180°, making them linear. These bond
angles are explained by the VESPR model.

Applying the nomenclature of hydrocarbons:

Nomenclature
Counted 7 C’s – Hept-
Only single bonds – -ane
Cyclic – yes – cyclo-

Cycloheptane
 Counted 5 Cs – Pent-
Has a double bond – -ene
Where is the double bond – 2
Cyclic – no

Pent-2-ene or 2-pentene
Counted 8 Cs – Oct-
Has a triple bond – -yne
Where is the triple bond – 4
Cyclic – no

Oct-4-yne or 4-Octyne.

There are two ways to represent hydrocarbons: 1.) The ball and stick model, and 2.) Skeletal formulas. The ball
and stick model is shown below:

The white atoms represent hydrogen, the black atoms represent carbon. The single stick between carbons and
hydrogens are single bonds.

Two sticks between carbon bonds are double bonds, and if there were three sticks connecting two carbon
atoms those would be triple bonds.

The skeletal formula is shown below:

Where each intersection and end of a line is a carbon atom. It is assumed that there are enough Hs bonded to
each C to fulfill the octet rule.

Organic compounds can be divided into their functional groups (heteroatoms or groups of heteroatoms
bonded to a hydrocarbon.) The functional groups shown in the Labster video for salicylic acid were:
1. Phenol group (Benzene bonded with OH/alcohol group)
2. Carboxylic acid group
This can be also thought of as:
1. Hydroxy group
2. Aromatic group
3. Carboxyl group

The phenol group was tested by adding ceric ammonium nitrate (CAN) to the unknown solutions. If positive
for an alcohol or phenol, the solution would turn dark red. This is an oxidative reaction due to losing an H
molecule.

And the carboxylic acid group was tested by adding sodium bicarbonate, which reacts to acid solutions
and creates effervescence. This is a substitution reaction.
REFERENCES
https://theory.labster.com/hydrocarbon_sidegroups/
https://www.chem.fsu.edu/chemlab/chm1046course/functional.html
Organic Chemistry, 3rd Ed. – Smith, J.G.
https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Supplemental_Modules_%28Organic_Chemistry
%29/Reactions/Addition_Reactions/Electrophilic_Addition_Reactions/Reactions_of_Alkenes_with_Bromine
https://www.organic-chemistry.org/chemicals/oxidations/ceriumammoniumnitrate-can.shtm
https://theory.labster.com/sodiumbi_test/
https://azchemistry.com/examples-organic-compounds-uses
https://www.biomadam.com/uses-of-organic-compound-in-daily-life
Sir Arthur Lagbas’ slides
http://www.chem.uiuc.edu/rogers/Text7/Tx73/tx73.html
https://chem.libretexts.org/Courses/University_of_Kentucky/UK
%3A_General_Chemistry/20%3A_Organic_Chemistry/20.1%3A_Hydrocarbons
https://www.softschools.com/examples/science/hydrocarbons_examples/320/
https://chem.libretexts.org/Bookshelves/General_Chemistry/Chemistry_(OpenSTAX)/20%3A_Organic_Chemis
try/20.1%3A_Hydrocarbons

Grading Criteria Score

Answers to Guide Questions (5 pts per item)
Generalization/Conclusion ( 5 pts)
References (5 pts)