Chapter 4: Carbon. Carbon Overview: Carbon—The Backbone of Biological Molecules All living...

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Chapter 4: Carbon

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Transcript of Chapter 4: Carbon. Carbon Overview: Carbon—The Backbone of Biological Molecules All living...

Page 1: Chapter 4: Carbon. Carbon Overview: Carbon—The Backbone of Biological Molecules All living organisms are made up of chemicals based mostly on the element.

Chapter 4: CarbonChapter 4: Carbon

Page 2: Chapter 4: Carbon. Carbon Overview: Carbon—The Backbone of Biological Molecules All living organisms are made up of chemicals based mostly on the element.

CarbonCarbon

• Overview: Carbon—The Backbone of Biological Molecules

• All living organisms are made up of chemicals based mostly on the element carbon

• Organic chemistry is the study of carbon compounds

• Overview: Carbon—The Backbone of Biological Molecules

• All living organisms are made up of chemicals based mostly on the element carbon

• Organic chemistry is the study of carbon compounds

Page 3: Chapter 4: Carbon. Carbon Overview: Carbon—The Backbone of Biological Molecules All living organisms are made up of chemicals based mostly on the element.

The Formation of Bonds with CarbonThe Formation of Bonds with Carbon

Carbon has FOUR unpaired valence electrons

This allows it to form FOUR covalent bonds with a variety of atoms

Carbon has FOUR unpaired valence electrons

This allows it to form FOUR covalent bonds with a variety of atoms

Page 4: Chapter 4: Carbon. Carbon Overview: Carbon—The Backbone of Biological Molecules All living organisms are made up of chemicals based mostly on the element.

Versatility of CarbonVersatility of Carbon

• The bonding versatility of carbon

• Allows it to form many diverse molecules, including carbon skeletons

• The bonding versatility of carbon

• Allows it to form many diverse molecules, including carbon skeletons

(a) Methane(a) Methane

(b) Ethane(b) Ethane

((c) Ethene c) Ethene (ethylene)(ethylene)

Molecular Molecular FormulaFormula

Structural Structural FormulaFormula

Ball-and-Ball-and-Stick ModelStick Model

Space-Filling Space-Filling ModelModel

HH

HH

HH

HH

HH

HH

HH

HH

HH

HH

HH HH

HHHH

CC

CC CC

CC CC

CHCH44

CC22HH

66

CC22HH44

Name andName and Comments Comments

Page 5: Chapter 4: Carbon. Carbon Overview: Carbon—The Backbone of Biological Molecules All living organisms are made up of chemicals based mostly on the element.

Common Bonding Partners of Carbon

Common Bonding Partners of Carbon

• The electron configuration of carbon

• Gives it covalent compatibility with many different elements

• The electron configuration of carbon

• Gives it covalent compatibility with many different elements

HH OO NN CC

HydrogenHydrogen

(valence = 1)(valence = 1)

OxygenOxygen

(valence = 2(valence = 2))

NitrogenNitrogen

(valence = 3)(valence = 3)

CarbonCarbon

(valence = 4)(valence = 4)

Page 6: Chapter 4: Carbon. Carbon Overview: Carbon—The Backbone of Biological Molecules All living organisms are made up of chemicals based mostly on the element.

HH

HHHH

HH

HH

HH HH HH

HH

HH

HH

HH HH HH

HH HH HH

HH HH

HH

HH

HH

HH

HH

HH

HH

HH

HH

HH HH HH HH

HH HH

HH HH

HH HH HH HH

HH HH

HH HH

HHHH

HHHH

HH

HH

HH

CC CC CC CC CC

CC CC CC CC CC CC CC

CCCCCCCCCCCCCCCC

CC

CC

CC

CC

CC

CC

CC

CCCC

CC

CC

CC

HH

HH

HH

HHHH

HH

HH

Length

Branching

Double bonds

Rings

Ethane Propane

Butane2-methylpropane

(commonly called isobutane)

1-Butene 2-Butene

Cyclohexane Benzene

HH HH HH HHHH

Page 7: Chapter 4: Carbon. Carbon Overview: Carbon—The Backbone of Biological Molecules All living organisms are made up of chemicals based mostly on the element.

HydrocarbonsHydrocarbons

Hydrocarbons

Are molecules consisting of only carbon (C) and hydrogen (H)

The bonds between the C and H atoms are non-polar covalent

This makes hydrocarbons hydrophobic

Hydrocarbons

Are molecules consisting of only carbon (C) and hydrogen (H)

The bonds between the C and H atoms are non-polar covalent

This makes hydrocarbons hydrophobic

Page 8: Chapter 4: Carbon. Carbon Overview: Carbon—The Backbone of Biological Molecules All living organisms are made up of chemicals based mostly on the element.

IsomersIsomers

Isomers

Are molecules with the same molecular formula but different structures and properties

• Three types of isomers are:

• Structural

• Geometric

• Enantiomers

Isomers

Are molecules with the same molecular formula but different structures and properties

• Three types of isomers are:

• Structural

• Geometric

• Enantiomers

Page 9: Chapter 4: Carbon. Carbon Overview: Carbon—The Backbone of Biological Molecules All living organisms are made up of chemicals based mostly on the element.

Structural isomers: Structural isomers: BranchingBranching

2-methyl butane2-methyl butanePentanePentane

Page 10: Chapter 4: Carbon. Carbon Overview: Carbon—The Backbone of Biological Molecules All living organisms are made up of chemicals based mostly on the element.

Geometric isomers: Geometric isomers: Double Double BondsBonds

ciscis isomer: The two Xs are isomer: The two Xs areon the same side.on the same side.

transtrans isomer: The two Xs areisomer: The two Xs areon opposite sides.on opposite sides.

Page 11: Chapter 4: Carbon. Carbon Overview: Carbon—The Backbone of Biological Molecules All living organisms are made up of chemicals based mostly on the element.

Enantiomers: Enantiomers: MirroredMirrored ImagesImages

AsymmetricAsymmetric Carbon Carbon

Page 12: Chapter 4: Carbon. Carbon Overview: Carbon—The Backbone of Biological Molecules All living organisms are made up of chemicals based mostly on the element.

The Functional GroupsThe Functional Groups

Functional groups

Are the chemically reactive groups of atoms within an organic molecule

They behave consistently and characteristically, giving unique properties to the molecules possessing them.

Functional groups

Are the chemically reactive groups of atoms within an organic molecule

They behave consistently and characteristically, giving unique properties to the molecules possessing them.

Page 13: Chapter 4: Carbon. Carbon Overview: Carbon—The Backbone of Biological Molecules All living organisms are made up of chemicals based mostly on the element.

STRUCTURE

EXAMPLE

NAME OFCOMPOUND

FUNCTIONALPROPERTIES

Methyl

5-Methyl cytidine is a component of DNA that has been modified by addition of the methyl group.

5-Methyl cytidine

Methylated compounds

Addition of a methyl group to DNA, or to molecules bound to DNA, affects expression of genes.

Arrangement of methyl groups in male and female sex hormones affectstheir shape and function.

Page 14: Chapter 4: Carbon. Carbon Overview: Carbon—The Backbone of Biological Molecules All living organisms are made up of chemicals based mostly on the element.

HydroxylHydroxyl

Composition: Oxygen bonded to a Hydrogen atom as well as a Carbon

Structure: -C-OH

Methanol:

Can also be seen as HO-C-

Not to be confused with hydroxide ion (OH-)

Compounds containing hydroxyl groups are called alcohols

Makes molecules polar (hydrophilic)

Composition: Oxygen bonded to a Hydrogen atom as well as a Carbon

Structure: -C-OH

Methanol:

Can also be seen as HO-C-

Not to be confused with hydroxide ion (OH-)

Compounds containing hydroxyl groups are called alcohols

Makes molecules polar (hydrophilic)

Page 15: Chapter 4: Carbon. Carbon Overview: Carbon—The Backbone of Biological Molecules All living organisms are made up of chemicals based mostly on the element.

CarbonylCarbonyl

Composition: Oxygen double bonded to a Carbon

Structure: -C=O

Aldehyde: If at end of carbon skeleton

Ketone: If in middle of carbon skeleton

Composition: Oxygen double bonded to a Carbon

Structure: -C=O

Aldehyde: If at end of carbon skeleton

Ketone: If in middle of carbon skeleton

Page 16: Chapter 4: Carbon. Carbon Overview: Carbon—The Backbone of Biological Molecules All living organisms are made up of chemicals based mostly on the element.

STRUCTURE

EXAMPLE

NAME OFCOMPOUND

FUNCTIONALPROPERTIES

Carboxyl

Acetic acid, which gives vinegar its sour taste

Carboxylic acids, or organic acids

Has acidic propertiesbecause the covalent bond between oxygen and hydrogen is so polar; for example,

Acetic acid Acetate ion

Page 17: Chapter 4: Carbon. Carbon Overview: Carbon—The Backbone of Biological Molecules All living organisms are made up of chemicals based mostly on the element.

STRUCTURE

EXAMPLE

NAME OFCOMPOUND

FUNCTIONALPROPERTIES

Amino

Because it also has a carboxyl group, glycine is both an amine anda carboxylic acid; compounds with both groups are called amino acids.

Amines

Acts as a base; can pick up an H+ from the surrounding solution (water, in living organisms).

Ionized, with a charge of 1+, under cellular conditions.

(ionized)(nonionized)

Glycine

Page 18: Chapter 4: Carbon. Carbon Overview: Carbon—The Backbone of Biological Molecules All living organisms are made up of chemicals based mostly on the element.

STRUCTURE

EXAMPLE

NAME OFCOMPOUND

FUNCTIONALPROPERTIES

Sulfhydryl

(may be written HS—)

Cysteine

Cysteine is an important sulfur-containing amino acid.

Thiols

Two sulfhydryl groups can react, forming a covalent bond. This “cross-linking” helps stabilize protein structure.

Cross-linking ofcysteines in hairproteins maintains the curliness or straightness of hair. Straight hair can be “permanently” curled by shaping it around curlers, then breakingand re-forming thecross-linking bonds.

Page 19: Chapter 4: Carbon. Carbon Overview: Carbon—The Backbone of Biological Molecules All living organisms are made up of chemicals based mostly on the element.

STRUCTURE

EXAMPLE

NAME OFCOMPOUND

FUNCTIONALPROPERTIES

Phosphate

In addition to taking part in many important chemical reactions in cells, glycerol phosphate provides the backbone for phospholipids, the most prevalent molecules in cell membranes.

Glycerol phosphate

Organic phosphates

Contributes negative charge to the molecule of which it is a part (2– when at the end of a molecule; 1– when located internally in a chain of phosphates).

Has the potential to react with water, releasing energy.


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