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Carbon: The backbone of life. Key concepts. Organic chemistry is the study of carbon compounds Carbon atoms can form diverse molecules by bonding to four other atoms A small number of chemical groups are key to the functioning of biological molecules.

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key concepts

Key concepts

  • Organic chemistry is the study of carbon compounds
  • Carbon atoms can form diverse molecules by bonding to four other atoms
  • A small number of chemical groups are key to the functioning of biological molecules
organic chemistry is the study of carbon compounds
Organic chemistry is the study of carbon compounds

The term “organic” chemistry came from the misconception that carbon-based compounds were always connected to life

organic chemistry is the study of carbon compounds4
Organic chemistry is the study of carbon compounds

The term “organic” chemistry came from the misconception that carbon-based compounds were always connected to life

Exception:

organic chemistry is the study of carbon compounds5

“Atmosphere”

CH4

Water vapor

Electrode

H2

NH3

Condenser

Cooled water

containing

organic

molecules

Cold

water

H2O

“sea”

Sample for

chemical analysis

Organic chemistry is the study of carbon compounds

Exception:

organic chemistry is the study of carbon compounds6
Organic chemistry is the study of carbon compounds
  • It mostly involves CHOPNS
  • With few elements it is possible to create a diversity of molecules

….because of the special properties of carbon

carbon atoms can form diverse molecules by bonding to four other atoms8
Carbon atoms can form diverse molecules by bonding to four other atoms

The key to an atom’s chemical characteristics is its electron configuration

Carbon’s valence shell is half-full…or is it half-empty?

carbon atoms can form diverse molecules by bonding to four other atoms9
Carbon atoms can form diverse molecules by bonding to four other atoms

Carbon usually completes its valence shell by sharing electrons with other atoms in covalent bonds

  • These bonds can be single
    • Tetrahedral shape
carbon atoms can form diverse molecules by bonding to four other atoms10
Carbon atoms can form diverse molecules by bonding to four other atoms

Carbon usually completes its valence shell by sharing electrons with other atoms in covalent bonds

  • Carbon can also form double bonds
  • Forms when two electrons are shared between two atoms
  • Forms a flat molecule
carbon atoms can form diverse molecules by bonding to four other atoms11
Carbon atoms can form diverse molecules by bonding to four other atoms

Carbon usually completes its valence shell by sharing electrons with other atoms in covalent bonds

carbon atoms can form diverse molecules by bonding to four other atoms12
Carbon atoms can form diverse molecules by bonding to four other atoms

Carbon usually completes its valence shell by sharing electrons with other atoms in covalent bonds

Would biological molecules be diverse if life was hydrogen-based?

carbon atoms can form diverse molecules by bonding to four other atoms13

Helium

2He

Hydrogen

1H

First

shell

Lithium

3Li

Beryllium

4Be

Fluorine

9F

Boron

5B

Nitrogen

7N

Neon

10Ne

Carbon

6C

Oxygen

8O

Second

shell

Chlorine

17Cl

Sodium

11Na

Aluminum

13Al

Silicon

14Si

Argon

18Ar

Magnesium

12Mg

Phosphorus

15P

Sulfur

16S

Third

shell

Carbon atoms can form diverse molecules by bonding to four other atoms
molecular diversity arising from carbon skeleton variation16

Ethane

Propane

1-Butene

2-Butene

(a) Length

(c) Double bonds

Butane

2-Methylpropane

(commonly called isobutane)

Cyclohexane

Benzene

(b) Branching

(d) Rings

Molecular diversity arising from carbon skeleton variation

Sources of diversity:

  • Chain length
molecular diversity arising from carbon skeleton variation17

Ethane

Propane

1-Butene

2-Butene

(a) Length

(c) Double bonds

Butane

2-Methylpropane

(commonly called isobutane)

Cyclohexane

Benzene

(b) Branching

(d) Rings

Molecular diversity arising from carbon skeleton variation

Sources of diversity:

  • Chain length

Hydrocarbons!

molecular diversity arising from carbon skeleton variation18

Ethane

Propane

1-Butene

2-Butene

(a) Length

(c) Double bonds

Butane

2-Methylpropane

(commonly called isobutane)

Cyclohexane

Benzene

(b) Branching

(d) Rings

Molecular diversity arising from carbon skeleton variation

Sources of diversity:

  • Chain length

Hydrocarbons!

Polar or non-polar?

molecular diversity arising from carbon skeleton variation19

Ethane

Propane

1-Butene

2-Butene

(a) Length

(c) Double bonds

Butane

2-Methylpropane

(commonly called isobutane)

Cyclohexane

Benzene

(b) Branching

(d) Rings

Molecular diversity arising from carbon skeleton variation

Sources of diversity:

  • Chain length
  • Branching
molecular diversity arising from carbon skeleton variation20

Ethane

Propane

1-Butene

2-Butene

(a) Length

(c) Double bonds

Butane

2-Methylpropane

(commonly called isobutane)

Cyclohexane

Benzene

(b) Branching

(d) Rings

Molecular diversity arising from carbon skeleton variation

Sources of diversity:

  • Chain length
  • Branching
  • Double bonds
molecular diversity arising from carbon skeleton variation21
Molecular diversity arising from carbon skeleton variation

Sources of diversity:

  • Chain length
  • Branching
  • Double bonds
molecular diversity arising from carbon skeleton variation22
Molecular diversity arising from carbon skeleton variation

Sources of diversity:

  • Chain length
  • Branching
  • Double bonds
  • Ring formation
other forms of diversity25
Other forms of diversity

Isomers-compounds that have the same numbers of atoms of the same elements, but different structures (hence different properties)

other forms of diversity26
Other forms of diversity

Three types of isomers

  • Structural
  • Geometric
  • Enantiomers
other forms of diversity27
Other forms of diversity

Three types of isomers

  • Structural isomers differ in the arrangement of their atoms or in the arrangement of double bonds

C4H8

other forms of diversity28

Ethane

Propane

1-Butene

2-Butene

(a) Length

(c) Double bonds

Butane

2-Methylpropane

(commonly called isobutane)

Cyclohexane

Benzene

(b) Branching

(d) Rings

Other forms of diversity

Three types of isomers

  • Structural isomers differ in the arrangement of their atoms or in the arrangement of double bonds
other forms of diversity29
Other forms of diversity

Three types of isomers

  • Structural isomers differ in the arrangement of their atoms or in the arrangement of double bonds

C4H10

other forms of diversity30

Ethane

Propane

1-Butene

2-Butene

(a) Length

(c) Double bonds

Butane

2-Methylpropane

(commonly called isobutane)

Cyclohexane

Benzene

(b) Branching

(d) Rings

Other forms of diversity

Three types of isomers

  • Structural isomers differ in the arrangement of their atoms or in the presence or absence of double bonds
other forms of diversity31
Other forms of diversity

Three types of isomers

  • Structural
  • Geometric isomers have the same covalent partnerships, but differ in their spatial arrangement (related to inflexibility of double bonds)
other forms of diversity32
Other forms of diversity

Three types of isomers

  • Structural
  • Geometric isomers have the same covalent partnerships, but differ in their spatial arrangement (related to inflexibility of double bonds)

i.e. cis v. trans fats

other forms of diversity33
Other forms of diversity

Three types of isomers

  • Structural
  • Geometric
  • Enantiomers are isomers that are mirror images of each other
a small number of chemical functional groups are key to the function of biological molecules35
A small number of chemical functional groups are key to the function of biological molecules
  • Properties of the molecule will also depend on the molecular components attached to the carbon skeleton
  • Functional groups can replace H
  • These groups participate in chemical reactions and change the molecular shape
a small number of chemical functional groups are key to the function of biological molecules36
A small number of chemical functional groups are key to the function of biological molecules

These differences in functional group in these two hormones drastically impact their function.

can you identify any of the common functional groups on the following biological molecules39

Adhesion

Water-conducting

cells

Direction

of water

movement

Cohesion

Can you identify any of the common functional groups on the following biological molecules?
slide42

Key concepts

  • Organic chemistry is the study of carbon compounds
  • Carbon atoms can form diverse molecules by bonding to four other atoms
  • A small number of chemical groups are key to the functioning of biological molecules