Carbon Compounds

Section 2.3

Lipids Fats/Oils/Steroids/Wax

4 Categories of Organic Molecules

Molecules of Life

Biochemicals

(CHON)Proteins

Enzymes/Structure/ Movement/Protection

Nucleic Acids(DNA/RNA)

CarbohydratesGlucose/Fructose

Starch/Cellulose

Carbon CompoundsOrganic Compounds

Carbohydrates

Monomer:Monosaccharide

Made up of:Carbon, Hydrogen,

Oxygen (H:O in 2:1 ratio)

Lipids

Monomer: Glycerol and Fatty Acids

Made up of: Carbon, Hydrogen,

Oxygen(H:O not in 2:1 ratio)

Proteins

Monomer: Amino Acid

Made up of: Carbon, Hydrogen, Oxygen, Nitrogen

Nucleic Acids

Monomer: Nucleotide

1) 5 Carbon sugar, 2) phosphate group 3)nitrogenous base

Made up of: Carbon, Hydrogen,

Oxygen, Nitrogen and Phosphorus

All compounds are either ORGANIC, containing carbon bonded to hydrogen and oxygen, or INORGANIC.

The chemistry of carbon is the chemistry of life.

Organic Compounds

Organic Compounds >11 million compounds Contain a C-C or C-H bond in combination with

N, O, S, P or halogens Simplest = CH4 Most complex = DNA

Organic CompoundsAllotropes of carbon

Allotropes: Different forms of an element in same physical state

Catenation: ability of an element to form chains and/or rings of covalently bonded atoms

Carbon has high bond energiesC-C 346 kJ/molC-H 418 kJ/mol

Diamond tetrahedral array of C

atoms o sp3 hybridized

high mp (>3500°C) hardest material known

to man brittle most dense (3.5x that of

H2O) Industrial uses: cutting,

drilling, grinding

Graphite layers of hexagonal

arrays of C atoms o sp2 hybridized (planar)

high mp no covalent bonds

between layers – C atoms too far apart from each other (London Dispersion forces)

layers slip past one another

lubricant and pencil “lead”

Graphite fibers (stronger and less dense than steel)- sporting goods and aircraft

Soot amorphous form of carbon (no structure)

impure carbon particles resulting from incomplete combustion

How many protons does carbon have? Electrons?

Carbon has FOUR valence electronso Needs eight electrons to be stable

Carbon readily forms four covalent bonds with other atoms, including carbon

Carbon Bonding:

Carbon Bonding Carbon can form straight chains, branched

chains, or ringso Leading to a great variety of organic

compounds

Isomers

Arrangement of Atoms Isomers – compounds that have the same

molecular formula but different structures

More C atoms in formula, more isomerso 18 isomers for C8H18o 35 isomers for C9H20o 75 isomers for C10H22

Isomers of C6H14

Ex #1) Butane, C4H10

Ex #2) Butene, C4H8

Ex #3) 2-Butene, C4H8

Ex #4) methyl propene, C4H8

ISO

MER

S

Structural Formula Indicates the number and types of atoms

present in a molecule and also shows the bonding arrangement of the atoms

One possible isomer of C4H10

Does not show 3D shape

Structural Isomers Isomers in which the atoms are bonded

together in different orders. C4H10 (note continuous chain of C atoms)

butane

methylpropane

Physical Properties of Structural Isomers

Melting Point (°C)

Boiling Point (°C)

Density at 20°C

Butane-138.4 -0.5 0.5788

Methylpropane -159.4 -11.633 0.549

Hydrocarbons Only have carbon and hydrogen Simplest organic compounds From petroleum (crude oil)

Single Bond Sharing 2 electrons A single line

Double Bond Sharing 4 electrons Two parallel lines

Triple Bond Sharing 6 electrons Three parallel lines

Carbon Bonding

Naming Carbon Compounds Organic PREFIXES Indicates the number of carbon atoms in the

hydrocarbon chain Hydrocarbon: any organic compound that

contains only the elements, hydrogen and carbon# of C prefix # of C prefix

1 Meth- 6 Hex-2 Eth- 7 Hept-3 Prop- 8 Oct-4 But- 9 Non-5 Pent- 10 Dec-

Organic PREFIXES Prefixes for alkanes that have 1-4

carbons are rooted historically. o These are methane, ethane, propane,

and butane, respectively. o An easy way to remember the first four

names is the anagram Mary Eats Peanut Butter (methane, ethane, propane, butane)

Prefixes for 5 carbons and up are derived from the Greek language.

Naming Carbon Compounds

Series Ending Formula determines the

# H atoms

Type of Bond(s)

Alkane -ane CnH2n+2 Single

Alkene -ene CnH2n Double

Alkyne -yne CnH2n-2 Triple

Organic SUFFIXES Indicates the types of covalent bonds that

are present in the hydrocarbon chaino Identifies the series to which it belongs

Aliphatic Hydrocarbons- hydrocarbons without aromatic

ringsSaturated

Hydrocarbons: compounds that contain all SINGLE bonds

Alkanes: each carbon is bonded to 4 atoms– Only contain single

bonds– Skeleton: C-C Molecular formula:

CnH2n+2

Unsaturated HydrocarbonsCompounds that contain at least one double bond or triple bond

1. Alkenes: compounds that contain a double bond

• Skeleton: C=C• Molecular formula = CnH2n

2. Alkynes: compounds that contain a triple bond

– Skeleton: CC– Molecular formula = CnH2n-2

Unsaturated Hydrocarbons

Naming Alkanes To give an alkane a name, a

prefix indicating the number of carbons in the molecule is added to the suffix aneo identifies both the kind of

molecule (an alkane) and how many carbons the molecule has (the prefix).

The name pentane tells you that the molecule is an alkane (-ane ending) and that it has 5 carbons (pent- indicates 5)

Naming Alkenes1. Locate the carbon atoms in the longest carbon chain

that contains the double bond. Use the stem with the ending –ene.

2. Number the carbon atoms of this chain sequentially, beginning at the end nearer the double bond. If the parent chain has more than 3 carbons, insert the number describing the position of the double bond (indicated by its 1st carbon location) before the base name.

1-butene 2-butene

http://wps.prenhall.com/wps/media/objects/476/488316/index.html

Named just like the alkenes except the suffix –yne is added

Naming Alkynes

1-butyne

2-butyne

ethyne

propyne

Write the names of the organic compounds

methane

propyne

1-pentene

2-pentene

nonane

3-hexene

2-butyne

1. ethene2. heptane3. 3-

decyne4. butane5. 2-

octene

Give the structural formulas for the organic compounds

Functional Groups An atom or group of atoms,

that replaces hydrogen in an organic compound and that defines the structure of a family of compounds and determines the properties of the family.

Female lion

Estradiol(estrogen)

HO

OH

OH

O Testosterone

Male lion

Hydroxyl

Carbonyl(middle)

Carboxyl

Lactic Acid {Amino

Urea

Wohler1828

FUNCTIONAL GROUP - a cluster of atoms that influence the properties of the molecules that they compose, and determine the characteristics of the compound.

Hydroxyl Group

Structure

Compound Name Alcohols

PropertiesPolar,

attracts water (good

solvent)

Carbonyl Group

Carbonyl (end):Structure

Compound Name Aldehydes

PropertiesStructural

isomers with different

properties

Carbonyl (middle):Structure

Compound Name Ketones

PropertiesStructural

isomers with different

properties

Carboxyl GroupStructu

re

Compound Name

Carboxylic acid

(organic acids)

Properties

Acidic properties

Amino GroupStructu

re

Compound Name Amines

Properties

Basic properties

Phosphate Group

Structure

Compound Name Phosphates

Properties

Makes the molecule and

anionTransfer energy

DNA

Methyl Group

Structure

Compound Name

Methylated compounds

Properties

May affect gene expression

Sulfhydryl GroupStructu

re

Compound Name Thiols

Properties

Stabilize proteins

Some can have a stinky odor –

skunk, rotten eggs, garlic

Methanethiol - It is a colorless gas with a distinctive putrid smell. It is a natural substance found in the blood and brain of humans and other animals as well as plant tissues. It occurs naturally in certain foods, such as some nuts and cheese. It is also one of the main compounds responsible for bad breath and the smell of flatus.

In many carbon compounds, the molecules are built up from smaller, simpler molecules known as MONOMERS.

Monomers can bind to one another to form complex molecules known as POLYMERS. o Large polymers are also called MACROMOLECULES o The process of reacting monomer molecules together in a

chemical reaction to form polymer chains or three-dimensional networks - POLYMERIZATION

Large Carbon Molecules:

WATER is the most important inorganic compound in the body and it participates in two biological reactions:o Hydrolysis o Dehydration Synthesis

Biological Reactions

Breaking down polymers by adding a water molecule.

Hydrolysis

Breaking down polymers by adding a water molecule.

C12H22O11 + H2O C6H12O6 + C6H12O6

Hydrolysis

Build up large molecules by releasing a molecule of water.

Dehydration Synthesis

Build up large molecules by releasing a molecule of water.

C6H12O6 + C6H12O6 C12H22O11 + H2O

Dehydration Synthesis

Enzyme Catalytic Cycle

The four main classes of organic compounds essential to all living things are made from CARBON, HYDROGEN, and OXYGEN atoms, but in different ratios giving them different properties.

Molecules of Life

Made of carbon, hydrogen, and oxygen with H to O in a 2:1 ratio

Monosaccharides are a single sugar - MONOMER

Source of energy Can be in straight or ring form -ose ending for sugars

Carbohydrates:

Glucose (C6H12O6) Ribose (C5H10O5)

Glucose, galactose, and fructose all have the same molecular formula but differ in the arrangement of atoms = ISOMERSo Molecular formula = C6H12O6 (hexoses)

C5H10O5 (pentoses)

Carbohydrates:

Type of Sugar

Name of Sugar Description of Sugar

Pentose ribose Found in RNA

Pentose deoxyribose Found in DNA

Hexose glucose In blood; cell’s main energy source

Hexose fructose In fruit; sweetest of monomers

Hexose galactose In milk

Carbohydrates:

Disaccharides are double sugars Two monosaccharides condense to form

disaccharideso Formed by dehydration synthesiso Molecular formula = C12H22O11

Carbohydrates

Bond that joins monosaccharides (carbohydrates) = glycosidic bond

Carbohydrates:

Carbohydrates

A disaccharide is produced by joining 2 monosaccharide (single sugar) units.

In this animation, 2 glucose molecules are combined using a condensation reaction, with the removal of water.

Glucose molecules joining to form a disaccharideCondensation of Monosaccharides

Name of Disaccharide

2 single sugars that join to form the

disaccharide Description of Sugar

Sucrose Glucose + Fructose Table Sugar

Lactose Glucose + Galactose

In milk

Maltose Glucose + Glucose In malt

Common Disaccharides

Carbohydrates Polysaccharides many sugars: General formula – (C6H10O5)n plus H2O (n = #

monomers) Formed by dehydration synthesis Long chains of glucose molecules

Name of Polysacchari

deDescription of Sugar

Glycogen(animal starch)

• Animal polysaccharide - stores excess sugar

• Stored in liver and muscles • Muscle contraction & movement

• Broken down into glucose and released into blood for quick energy

Starch • Plant polysaccharide• Stores excess sugar

Cellulose

• Gives plants strength and rigidity• Major component of wood and paper

• Component of cell wall

Carbohydrates:

Elements – carbon, hydrogen, and oxygen (NOT a 2:1 H:O ratio)

Do not dissolve in water Lipids contain a large number of C-H bonds which store

more energy than C-O bonds in carbohydrates Monomers: glycerol and fatty acid

Lipids: Fats, Oils, and Waxes

Fatty Acids:o Fatty acids are unbranched C-chains (12-28 C) with

a carboxyl group (acid) at one end• The carboxyl end is POLAR and attracted to water –

HYDROPHILIC• The hydrocarbon end is NONPOLAR and does not interact with

water – HYDROPHOBIC

Lipids:

Fatty AcidGeneral

Structure

Saturated (single bonds)

Unsaturated (double bonds)

Three major roles of lipids in living organisms:o Lipids can be used to store energyo Lipids are important parts of biological membraneso Lipids are waterproof coverings

Lipids:

Saturated Fatty Acids

• Carbon atoms with 4 atoms covalently bonded

• All single bonds

• High melting points• Solid @ room temperature• Ex.) animal fat, shortening

Unsaturated Fatty Acids

• Carbon not bonded to the maximum # of atoms

• There are double bond(s)• polyunsaturated

• Liquid @ room temperature• Primarily in plants• Energy storage in animals

Saturated & Unsaturated Fatty Acids

Saturated and Unsaturated Fatty Acids:

Lipids (fats, oils, and waxes) are formed by a glycerol molecule bonding to fatty acid(s) o formed by dehydration synthesis

Lipids

Dehydration Synthesis:

Three fatty acids attached to glycerol

Triglycerides

Formation of a Triglyceride

Two fatty acids joined to a glycerol Makes up cell membrane - PHOSPHOLIPID BILAYER

Phospholipids

Elements: Carbon, Hydrogen, Oxygen, Nitrogen Monomer: AMINO ACID (20 different kinds) Each amino acid has a central carbon atom bonded

to 4 other atoms or functional groups

Proteins

Proteins Bond that joins amino acids (protein) = PEPTIDE

BOND

Formation of a peptide bond

amino acid 1 amino acid 2 dipeptide water

Peptide bondFormation of a peptide bond

Proteins

1. Control the rate of reactions2. Regulate cell processes3. Form important cellular structures4. Transport substances into or out of cells5. Help to fight disease

Functions of Proteins

Enzyme + Substrate = ES complex EP complex = Enzyme + product(s)

Enzymes and Substrates:

Enzymes (Proteins)

Enzyme Catalytic Cycle

Protein that has lost its active conformation, or shape

Denaturing caused by:o Temperatureo Solute (salt) Concentrationo pH

Denaturing Proteins:

Large, complex organic compounds that store information in cells, using a system of four compounds to store hereditary information, arranged in a certain order as a code for genetic instructions of the cell.

Elements: Carbon, Hydrogen, Oxygen, Nitrogen, Phosphorus Monomer: Nucleotide1. Phosphate group (Phosphoric Acid)2. 5-carbon (pentose) sugar (Deoxyribose or Ribose)3. Nitrogenous Base

Nucleic Acids

Nitrogenous Bases There are FOUR Nitrogen bases

Nucleic Acids Nucleotides combine, in DNA to form a double

helix, and in RNA a single helix The sides of the ladder are made up of the phosphate group and the sugar and the rungs of the ladder are nitrogen bases Examples of Nucleic Acids:

1. Deoxyribonucleic Acid (DNA)2. Ribonucleic Acid (RNA)

Nucleic Acids and Dehydration Synthesis