Organic Chemistry Introduction to organic chemistry Principles of carbon chemistry Principle of polymers Hydrocarbons Organic chemistry and biochemistry.

Organic Chemistry

• Introduction to organic chemistry

• Principles of carbon chemistry

• Principle of polymers

• Hydrocarbons

• Organic chemistry and biochemistry

• Take Home Message

Organic Chemistry

• Introduction to organic chemistry

• Principles of carbon chemistry

• Principle of polymers

• Hydrocarbons

• Organic chemistry and biochemistry

• Take Home Message

Elements of the Solar System: Importance of Carbon

• 25 of 92 natural elements are known to be essential to life on Earth

• Four of the above make up 96%!– Carbon (C), Oxygen (O), Hydrogen (H) and

Nitrogen (N)

• Compare to solar abundance and discuss relative to evolution of biochemistry in origin of life

Elements of the Periodic Table

Relative Abundance of Elements in the Sun

0

2

4

6

8

10

12

0 5 10 15 20 25 30 35 40 45

Atomic Number

Lo

g o

f R

ela

tiv

e

Ab

un

dan

ce (

Si)

H

He

Li

Be B

C

C

N

O

Fe

Ne

Na

Mg

Al

Si

P

S

Cl

Ar

K

Ca

Fe

Frequency of Carbon

• Carbon as a building block– C is the 4th most common element in the solar system

– Probably the same frequency elsewhere in the Universe

• Conclusion: C is common throughout the Universe and is likely to behave similarly (C and its tendency to form covalent bonds) in most environments

Chemistry Subdivisions

• Organic Chemistry– Chemistry of compounds in which C is the

principal element (biotic/living and abiotic/non-living)

• Inorganic Chemistry– Chemistry of all other elements

• Significance of C in chemistry

Organic Chemistry

• Introduction to organic chemistry

• Principles of carbon chemistry

• Principle of polymers

• Hydrocarbons

• Organic chemistry and biochemistry

• Take Home Message

Principles of Carbon Chemistry: C’s Atom

• C is unparalleled in its ability to form molecules that are large, complex and diverse in structure

• Key is the C atom (protons, electrons, and quantum mechanics)– C has ____ electrons– Little tendency to gain or loose electrons (i.e., no ionic bonding)– Greater likelihood for electrons to be shared in covalent bonds– Possible covalent bonds per atom from __ to ___– Most common elements with which C bonds

• O, H, N and C (compare with prominence in living systems)

Principles of Carbon Chemistry: Linkages among Carbon Atoms

• Linkages among C atoms form macromolecules (define)– Chains of C (methane and ethane)– Branches of C – Rings of C (e.g., benzene)

Principles of Carbon Chemistry: Functional Groups

• Distinctive features of C macromolecules is a function of two aspects of the molecules– Carbon skeleton (chains, branches, rings)

• Chains, branches or rings• Number of C atoms (2, 3, 4, etc.)

– Groups of atoms attached to carbon skeleton • Called functional groups (some example)

– Hydroxyl (OH)– Amino (NH2)– Phosphate (P)– Total of five different functional groups

Organic Chemistry

• Introduction to organic chemistry

• Principles of carbon chemistry

• Principle of polymers

• Hydrocarbons

• Organic chemistry and biochemistry

• Take Home message

Principle of Polymers: Introduction

• Principle of hierarchy theory and emergent properties

• Small molecules joined together to form large molecules up to 1,000’s of C atoms

• Macromolecules

• Infinite array of possible combinations, each with its own unique chemistry

Principle of Polymers

• In living systems, polymers of C results in four major classes of compounds that are of extreme importance– Carbohydrates– Proteins– Nucleic acids– Lipids

• Linkages between C atoms via covalent bonds• Calculating potential diversity of C polymers

– Analogy to alphabet (26 letters) and infinite ways to “create words”– If 45 basic different C alphabet pieces, infinite ways to create

polymers of C

Organic Chemistry

• Introduction to organic chemistry

• Principles of carbon chemistry

• Principle of polymers

• Hydrocarbons

• Organic chemistry and biochemistry

Hydrocarbons

• Carbon compounds with only two elements:– C and H

• C-C bonding via covalent bonds (nonpolar)• Number of bonds

– 1, 2, 3, or 4• Most simple compound is methane

HH C H H

Hydrocarbons: C to C Bonding

• C to C bond can be single bond (C-C) H H

– Ethane H C-C H H H

• C to C bond can be double bond (C = C)H H

– Ethene C = CH H

• C to C bond can be triple bond (C = C)– Ethyne H C = C H

Hydrocarbons: Groups

• Alkanes– Single covalent bond between C atoms

• Methane (C1H4)• Ethane (C2H6)• Propane (C3H8)• Butane (C4H10)• Pentane (C5H12)• Octane (C__H18)• Decane (C__H22)• Pattern: CnH2n+2)

• Alkynes (triple bond C = C)• Alkenes (double bond or C = C)• Aromatics (rings or cyclic C atoms)

– Example (C6H6)

Hydrocarbons: Saturated and Unsaturated Hydrocarbons

• Saturated hydrocarbons: maximum number of H atoms bonded to C

H H

– Ethane or H C - C H

H H

• Unsaturated hydrocarbons: anything else H H

– Ethylene or C = C

H H

Organic Chemistry

• Introduction to organic chemistry

• Principles of carbon chemistry

• Principle of polymers

• Hydrocarbons

• Organic chemistry and biochemistry

• Take Home Message

Organic Chemistry and Biochemistry

• Keys:– Structure of basic unit– Polymer structure– Functional group (e.g., OH, P or NH2)

• Types of C polymers for biotic systems– Carbohydrates– Lipids– Proteins– Nucleic acids

Organic Chemistry and Biochemistry: Monomers

• Carbohydrates– Glucose or C6H12O6

– Functional unit: hydroxyl or OH-• Proteins

– Amino acid – Functional unit: amine or NH2

• Nucleic Acids– Nucleotide or – Functional units: organic N base, carbohydrate, and phosphate

• Lipids– Fatty acids C16-18

– Functional unit: glycerol (3 OH- groups)

Organic Chemistry

• Introduction to organic chemistry

• Principles of carbon chemistry

• Principle of polymers

• Hydrocarbons

• Organic chemistry and biochemistry

• Take Home Message

Take Home Message

• While the molecule of water is simple but exquisite and unique in its chemical behavior, the C atom is unusual and unique in its chemical behavior but for different reasons– Covalent bonding– Valence electrons

• Unusual behavior of C results in extreme array of simple to very complex molecules as a function of– Polymers – Functional groups

• Life as we know it is hard to imagine without C behaving as a polymer with covalent bonds to create carbohydrates, proteins, nucleic acids and lipids (C polymers)

• Principle of hierarchy theory and emergent properties

Exam Coverage

• Text– Chapter 9 (Atomic Structure; entire chapter)– Chapter 10 (Elements & Periodic Table; entire chapter)– Chapter 11 (Compounds and Chemical Change; entire chapter

excluding pages noted in lecture and posted on the www)– Chapter 12 (Chemical Formulas; ONLY: pp 278-279; p 292 - Units

of Measurement)– Chapter 13 (Water & Solutions; exclude pp 306-310 (electrolytes,

boiling point, and freezing point)• Lecture Notes

– Atoms and Elements; Valence Electrons and Bonding; Water; and Organic Chemistry

• Labs– Physics: Electricity and Light– NO OTHER LABS FOR THIS EXAM

Help or Desperation Sessions

• Tuesday @ 5:00 PM in Honors Lounge

• Wednesday @ 6:30 Pm in Honors Lounge

• No lecture, questions only