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Organic Chemistry:
Carbon and the Molecular
Diversity of Life
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Organic Chemistry

Organic chemistry is the study of carbon compounds

Organic compounds range from simple molecules to colossal
ones.

Most organic compounds contain hydrogen atoms in addition

to carbon atoms.

Compounds containing only carbon and hydrogen are called

hydrocarbons; they are commonly used as a fuel source.
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Biological Molecules

Carbon is the backbone of biological

molecule.

Carbon has the ability to form long chains.

This property allows the formation of large

biomolecules (such as proteins, lipids,
carbohydrates, and nucleic acids).
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Carbon

Carbon has four valence electrons to make covalent bonds

Carbon atoms can form diverse molecules by bonding to four

other atoms

Recall that electron configuration is the key to an atom’s

characteristics because it determines the kinds of bonds and
number of bonds an atom will form with other atoms
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1 Organic chemistry is a science based on the

study of ___________________.

A compounds that can only be made by living cells.

B vital forces interacting with matter.
C carbon compounds.
water and its interaction with other kinds of
D
molecules.
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2 Which property of the carbon atom allows it to

bond with many different elements?

A Carbon has 6 to 8 neutrons.

B Carbon has 4 valence electrons.
C Carbon forms ionic bonds.
D A and C only
E A, B, and C
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3
How many electron pairs does carbon share in order to
complete its valence shell?

A 1
B 2
C 3
D 4
E 8
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4 What type/s of bond/s does carbon have a tendency

to form?

A Ionic
B Hydrogen
C Covalent
D A and B
E A, B and C
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Hydrocarbons

Hydrocarbons are compounds made up of carbon and hydrogen

atoms

Aliphatic hydrocarbons: compounds with carbon atoms connected

in a straight chain

Aliphatic compounds consist of three classes of compounds:

Alkanes
Alkenes
Alkynes

Aromatic hydrocarbons: compounds with carbon atoms connected

in cyclic (ringed) structures that have an odor
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Aliphatic hydrocarbons: Alkanes

Hydrocarbon chains where all the bonds between carbons
are SINGLE bonds

They are also known as saturated hydrocarbons. They are

“saturated” with hydrogens.

Name uses the ending -ane

Examples: Methane, Propane, Butane, Octane
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Alkanes
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Alkanes
The general formula CnH2n+2

n = number of carbon atoms

CH4 Methane ______ Hexane

C 2H 6 Ethane ______ Heptane

C 3H 8 Propane ______ Octane

C4H10 Butane ______ Nonane

C5H12 Pentane ______ Decane

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Straight Chain Alkanes

Straight chain alkanes are alkanes that

have all their carbon atoms connected in a row.

These are structural formulas.

CH3-CH2-CH3 This is a condensed formula for propane.

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Branched Chain Alkanes

Branched chain alkanes are alkanes that have a branching
connection of carbons.

For example, butane has the formula C4H10.

Shown below are the straight chain and branched forms of butane.

CH3-CH2-CH2-CH3

Straight chain butane

Branched chain butane
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Alkanes

Hydrocarbons are non polar, since the difference in electronegativity

between C and H is below 0.5. Note that larger molecules are more
polarizable and therefore have stronger London dispersion forces which
increases boiling point.
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5 What is the reason why hydrocarbons are not

soluble in water?

The majority of their bonds are polar

A
covalent C-H linkages
The majority of their bonds are nonpolar
B
covalent C-H linkages
C They are hydrophilic

They exhibit considerable molecular complexity

D
and diversity
E They are lighter than water
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6 Gasoline and water do not mix because gasoline

is __________.

A less dense than water

B less viscous than wtaer

C nonpolar and water is polar

D volatile and water is not

E polar and water is nonpolar

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7 Which substance would be the most soluble in

gasoline?

A water
B sodium nitrate, NaNO3

C hydochloric acid, HCl

D hexane, C6H14

E sodium chloride, NaCl

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Aliphatic hydrocarbons: Alkenes

Alkenes have at least one double bond between two carbon

atoms. General formula: CnH2n where n = # of carbon atoms

The name uses the ending -ene.

The simplest alkenes are:

C2H4 Ethene (from 2-carbon parent, ethane)

C 3H 6 Propene (from 3-carbon parent, propane)

Ethene
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Aliphatic hydrocarbons: Alkynes

Alkynes have at least one triple bond between two carbon atoms.
General formula: C H where n = # of carbon atoms
n 2n-2
The name uses the ending -yne.
The simplest alkynes are:

C2H2 Ethyne (commonly known as acetylene)

C3H4 Propyne or propylene

Ethyne
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Representing Aliphatic Hydrocarbons

Ball and stick Space filling Structural Molecular
model model formula formula
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Cycloalkanes

Carbon can also form ringed structures.

Five- and six-membered rings are most stable.

They can take on
conformations in which
their bond angles are very
close to the tetrahedral
angle.

Smaller rings are quite

strained
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Aromatic hydrocarbons

They have benzene ring structure ( hexagon) and have particular

aroma associated with it.

CH3

Benzene
Toluene ( methyl benzene)
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8 Hydrocarbons

A are polar.
B are held together by ionic bonds.
C contain nitrogen.
D contain only hydrogen and carbon atoms.

E are held together by hydrogen bonds.

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9 Hydrocarbons containing only single bonds

between the carbon atoms are called __________.

A alkenes

B alkynes

C aromatics

D alkanes

E ketones
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10 The general formula of an alkane is _______.

A C2nH2n+2
B CnH2n
C CnH2n+2
D CnH2n-2
E CnHn
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Which is the formula of an alkane?

11

A C10H10
B C10H18
C C10H20
D C10H22
E C10H24
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12 The molecular geometry of each carbon aton in an

alkane is ________.

A octahedral

B sqaure planar

C trigonal planar

D tetrahedral

E trigonal pyramidal
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13 Hydrocarbons containing carbon-carbon triple

bonds are called________.

A alkenes

B alkynes

C aromatics

D alkanes

E ketones
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Which is the formula of an alkyne?

14

A C10H10
B C10H18
C C10H20
D C10H22
E C10H24
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An alkene has at least one ________ and has the

15 general formula ______.

A C-C single bond, CnH2n+2

B C-C double bond, CnH2n
C C-C triple bond, CnH2n
D C-C double bond, CnH2n-2
E C-C triple bond, CnH2n-2
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16 ________ could be the formula of an alkene.

A C 3H 8
B C 3H 6
C C 6H 6
D C17H36
E CH8
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17 Which of the following hydrocarbons has a double

bond in its carbon skeleton?

A C 3H 8

B C 2H 6

C CH4

D C 2H 4

E C 2H 2
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18 The compound below is an _________.

A alkyne

B alkene

C alkane

D aromatic compound

E olefin
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19 The gasoline consumed by an automobile is a

fossil fuel consisting mostly of

A aldehydes
B amino acidd
C alcohols
D hydrocarbons
E thiols
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Isomers

Hydrocarbons exhibit a phenomenon called isomerism- existence of

different molecular arrangement but same formula

Isomers are compounds with the same molecular formula but different
structures and properties.

There are 3 different types of isomers:

Structural isomers
click here for an animation
Geometric isomers on Isomers

Enantiomers
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Structural Isomers

Structural isomers have different covalent arrangements

of their atoms.

These three compounds all have the same molecular

formula, but differ in which atoms are bonded together.
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Geometric Isomers
Geometric isomers must contain a C=C double bond.

Geometric isomers have the same covalent arrangements but

differ in spatial arrangements. Geometric isomers are referred to
as either cis or trans.

cis isomer trans isomer:

The two CH3 groups are The two CH3 groups are
on the same side. on opposite sides.
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Enantiomers

Enantiomers are isomers that are mirror images of each other.

Enantiomers cannot be superimposed on each other.

Enantiomers differ in spatial arrangement around an asymmetric

carbon, resulting in molecules that are mirror images, like left and
right hands. The two isomers are designated the L and D isomers
from the Latin for left and right (levo and dextro).
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20 Structural isomers are molecules that:

A are enantiomers.
B are hydrocarbons.
C have a ring structure.
D are mirror images.
differ in the covalent arrangements of their
E
atoms.
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21 The two molecules shown are best described as

A optical isomers

B radioactive isotopes

C structural isomers

D nonradioactive isotopes

E geometric isomers
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22 Which of the following is true of geometric isomers?

A
They have variations in arrangement around a double
bond.

B
They have an asymmetric carbon that makes them
mirror images.

C They have the same chemical properties.

D They have different molecular formulas.

E
Their atoms and bonds are arranged in different
sequences
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Functional groups

A functional group is an atom or group of atoms that imparts

special physical and chemical properties to the compound

Based on the functional group, the compounds are classified

as follows.

Haloalkanes/alkenes/alkynes
Alcohols
Acids
Amines
Ketones
Aldehydes
Esters
Ether
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Halo- alkanes/alkenes/alkynes

Haloalkanes, haloalkenes, and haloalkynes are characterized by

the presence of a halogen atom (F, Cl, Br or I), in place of a
hydrogen atom.

CH3Cl, CH2Cl2 , CHCl3, CCl4, CBr4, F2C=CF2 , FC = CF

They are formed when one or more H atoms are replaced by

halogen atom/s.
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Alcohols

Alcohols contain the functional group -OH (hydroxyl group).

For example, in CH4, one H is replaced by -OH

The name ends with -ol, drop the alkane "e" add "ol",
So, methane becomes methyl alcohol or methanol, CH3OH.

CH3CH2OH is called ethyl alcohol or ethanol.

Thiols contain the functional group -SH, (sulfhydryl group)

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Naming Alcohols

Alkane Alcohol Alcohol

Alkane name
formula formula name

CH4 methane CH3OH methanol

C 2H 6 ethane C2H5OH ethanol

C 3H 8 propane C3H7OH propanol

C4H10 butane C4H9OH butanol

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23 Which of the following statements is true

concerning a compound that contains a
hydroxyl group?

A It lacks an asymmetric
carbon, and it is probably
a fat or lipid.

B It should dissolve in water.

C It should dissolve in a
nonpolar solvent.

D It won't form hydrogen

bonds with water.
E It is hydrophobic.
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24 In which of the structures are the atoms bonded

ionic bonds?

A A

B B

C C

D C, D, E

E None of the structures

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Carboxylic acids
The functional group is -COOH

Replace one H atom in the alkane by a -COOH group

HCOOH = Methanoic acid or formic acid

CH3COOH = Ethanoic acid or acetic acid or vinegar

CH3CH2COOH = Propanoic acid

Drop the "e" from the parent alkane and add "oic acid"

C
C C OH
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Amines
The functional group is - NH2

CH3NH2, replace one H by an -NH2 group

CH3NH2 Amino methane or Methyl amine

More than one functional groups, same or different are common in

organic compounds

example: amino acids. They have amine and acid groups

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25 Which of the structures contain(s) a carboxyl

group?

A A

B B

C C

D C&E

E None of the structures

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26 What is the name of the functional group shown in the

following figure?

A carbonyl
B ketone
C aldehyde
D carboxyl
E hydroxyl
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27 Which two functional groups are

always found in amino acids?

A ketone and aldehyde

B carbonyl and carboxyl
C carboxyl and amino
D phosphate and sulfhydryl
E hydroxyl and aldehyde
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Ketones

The functional group is -C=O or "carbonyl" group

Usually sandwiched between two carbon groups

CH3CH2CH3 = propane
CH3CO CH3 propanone or acetone ( nail polish remover)
Drop e and add none

CH3COC2H5 Ethyl methyl ketone or butanone

H3C- C- CH3
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Ketones
A function the functional group can make!

Estrogen- has
two hydroxyl
groups in it.

Testosterone - one
hydroxyl group is
replaced by a ketone.
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Aldehydes

The functional group is -CHO with a C=O bond

drop 'e' of the parent alkane and add 'nal'

HCHO - (1 carbon) Methanal or Formaldehyde

CH3CHO- (2 carbon) Ethanal or Acetaldehyde

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Aldehydes, Ketones and Acids

The way the carbonyl group is bonded to the main body of the
molecule is different in acids, ketones and aldehydes

The C=O is between two other carbon

atoms ( alkyl groups) in the molecule

The C=O group is at the end ( terminal carbon) of

the molecule and should be connected to a H atom

The C=O bond should be connected to an OH group

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28 What is the name of the

functional group shown in the
following figure?
(R = any carbon group)
R-C=O

A carbonyl
B ketone
C aldehyde
D carboxyl
E hydroxyl
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Ester

The functional group is -COOR where R could

be another alkyl group. Esters are formed by
the combination of an acid and an alcohol by
eliminating one molecule of water.

They are usually pleasant smelling compounds

( natural oils and essence)

CH3COOH + CH3OH --> CH3COOCH3

CH3COOCH3 methyl acetate

CH3COOC2H5 ethyl acetate

C2H5COOCH3 methyl propanoate

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Ether
The functional group is an O atom sandwiched
between two carbon groups

CH3-O- CH3 dimethyl ether

They are highly flammable and used as solvents

in organic synthesis
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Groups with a Carbon–Oxygen Double Bond

(Carbonyl Groups)
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Amides
Amides are formed by the reaction of
carboxylic acids with amines.

RCOOH + H2NR' -->

-H O
2

CONH linkage is known as the amide linkage ( peptide) in

proteins

This linkage is formed when several amino acids join with their
acid and amino groups together.
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29 Which is the best description of a carbonyl group?

A an oxygen joined to a carbon by a single covalent bond

B a nitrogen and two hydrogens joined to a carbon by covalent bonds

C a carbon joined to two hydrogens by single covalent bonds

D a sulfur and a hydrogen joined to a carbon by covalent bonds

E a carbon atom joined to an oxygen by a double covalent bond

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30 What is the name of the functional group

shown below.
A carbonyl
B ketone
C aldehyde
D carboxyl
E hydroxyl
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31 Which of the following contains nitrogen in

addition to carbon, oxygen, and hydrogen?

A an alcohol such as ethanol

B a monosaccharide such as glucose
C a steroid such as testosterone
D an amino acid such as glycine
E a hydrocarbon such as benzene
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32 What type of functional group is shown in the

compound below?

A carbonyl
B ketone
C aldehyde
D carboxyl
E hydroxyl
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33 Which molecule contains an amine functional

group?
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34 Which molecule contains an aldehyde

functional group?
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35 Which molecule contains an alcohol

functional group?
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36 Which one of the following is not an alcohol?

A acetone

B glycerol

C ethanol

D cholesterol

E ethylene glycol
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Macromolecules

Macromolecules are large molecules composed of smaller

molecules.

They are complex in their structures.

Carbon has the unique property of joining together via

covalent bonding to form large (macro) molecules.

Most macromolecules are polymers, built from monomers.

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Macromolecules

Three of the classes of life’s organic molecules are polymers:

Proteins
Carbohydrates
Nucleic acids

There are some macromolecules that are not polymers:

lipids
phospholipids
steroids
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Polymers
Although organisms share the same limited number of monomer
types, each organism is unique based on the arrangement of
monomers into polymers

An immense variety of polymers can be built from a small set of

monomers

Polymer Made of these monomers

Proteins Amino acids

Carbohydrates Simple sugars (monosaccharides)

Nucleic acids Nucleotides

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Polymers
Is a long molecule consisting of many similar
building blocks called monomers

Monomers form
larger molecules by
condensation
reactions called short polymer
Monomer

dehydration
reactions

longer polymer
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Amino Acids and Proteins

Proteins are formed when several amino

acids combine together

Acid and amine end of the molecules join

together to form long peptide chain

Peptide chain with 50 or more amino acids

can form an individual protein.
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Carbohydrates (sugars)
Simple sugars are poly-hydroxy aldehydes or ketones.

Table sugar, (sucrose) is made up of glucose and fructose.

They all have several hydroxyl groups in their structure that

makes them soluble in water.

C
Glucose and fructose are
monosaccharides.

Sucrose is a disaccharide.

glucose fructose
(monosaccharide)
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Carbohydrates (sugars)
In solution, they form cyclic structures.

These can form chains of sugars that form structural

molecules such as starch and cellulose.
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Nucleic Acids

Nucleic acids are made up of

monomer units called
nucleotides

Sugar + Base + PO43- = nucleotide

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Nucleic Acids
Two of the building blocks of RNA and DNA are
sugars (ribose or deoxyribose)

and cyclic bases (adenine, guanine, cytosine, and thymine or uracil)

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RNA DNA
Acid Ribonucleic acid Deoxyribonucleic acid

Sugar ribose deoxyribose

Bases A, C, G and U A, C, G and T

Function make proteins carry genetic code

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Nucleic Acids

Nucleotides combine to form the

familiar double-helix form of the
nucleic acids

The blue ribbon is the sugar/

phosphate backbone

The bases are the rungs in the

(spiral) ladder

The nucleotides join together via

hydrogen bonding through their
bases
A-T, C-G etc.
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37 Which of the following is not one of the four

major groups of macromolecules found in living
organisms?

A glucose
B carbohydrates
C lipids
D proteins
E nucleic acids
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38 Glucose is a type of _______.

A amino acid
B protein
C carbohydrate
D nucleotide
E nucleic acids
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39 Nucleic acids are made up of __________.

A amino acids
B proteins
C carbohydrates
D nucleotides
E sugars
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40 A nucleotide consists of _____________.

A glucose + fructose + amino acid

B glucose + fructose + phosphate group
C amino acid + protein + phosphate group
D sugar + base + amino acid
E sugar + base + phosphate group
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41 Polymers of polysaccharides and proteins are

all synthesized from monomers by which
process?

connecting monosaccharides together

A
(condensation reactions)
B the addition of water to each monomer (hydrolysis)
C the removal of water (dehydration reactions)
D ionic bonding of the monomers
the formation of disulfide bridges
E
between monomers
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Other complex molecules of life

Fats and Lipids

Are a diverse group of hydrophobic molecules

Are the one class of large biological molecules that

do not consist of polymers

Share the common trait of being hydrophobic

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Fats and Fatty Acids

Fats
Are constructed from two types of smaller molecules, a single
glycerol and usually three fatty acids

Fatty acids
Carboxylic acids with a very long chain of carbon atoms.
Vary in the length and number and locations of double bonds
they contain

CH2OH

CH2OH

CH2OH

a fatty acid
glycerol
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Dehydration Synthesis

The attachment of a fatty acid to glycerol results in a

removal of a water molecule.
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The diagram shows three fatty acids added to

glycerol producing a fat molecule.
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Saturated and Unsaturated Fatty Acids

Saturated fatty acids

Have the maximum number of
hydrogen atoms possible

Have no double bonds in their

carbon chain

Mainly animal origin

Unsaturated fatty acids

Have one or more double bonds

When hydrogenated ( add more Hydrogen)

they become solid and saturated

Mainly plant origin

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Phospholipids

Have only two fatty acids

Have a phosphate group instead of a

third fatty acid

Results in a bilayer arrangement found

in cell membranes
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Steroids

Are lipids characterized by a carbon skeleton consisting of three

or more fused rings

cholesterol
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42 Which of the following is (are) true for the

class of large biological molecules known as
lipids?

A They are insoluble in water.

B They are an important constituent of cell membranes.
They provide the least amount of energy in
C
living organisms
D Only A and B are correct.
E A, B, and C are correct.
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43 Saturated fatty acids

A are the predominant fatty acid in corn oil.

have double bonds between carbon atoms of the

B
fatty acids.

have a higher ratio of hydrogen to carbon than do

C
unsaturated fatty acids.
D are usually liquid at room temperature.

E are usually produced by plants.

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44 The hydrogenation of vegetable oil would

result in which of the following?

a decrease in the number of carbon-carbon

A
double bonds in the oil (fat) molecules

an increase in the number of hydrogen

B
atoms in the oil (fat) molecule

the oil (fat) being a solid at room

C
temperature

D A and C only

E A, B, and C
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