Organic Chemistry - Introductory Concepts

I. Characteristics of Organic Compounds

A. B. C. D. E. F. G. H. I. J. II.

Contain Carbon Most Are Flammable Have Low Melting Points Have Low Boiling Points Soluble in Nonpolar Liquids Insoluble in Water (Polar Liquid) Contain Covalent Bonds Contain Many Atoms Have Complex Structures Do Not Conduct Electricity (Molten or In Soln)

Characteristics of Organic Reactions A. Take Place Between Molecules

B.

Are Slow

C.

Gives Varied Products - Side Reactions

D.

May Not Go Far Toward Completion - Low Yield

E.

Involve Only A Portion Of The Molecule - Functional Group

III.

Unique Features of Carbon A. Forms Bonds with Self To Give Chains Or Rings

B.

Form Multiple Bonds With Itself

C.

Forms Strong Covalent Bonds (Single & Multiple) With Other Elements

D.

Isomers Are Possible - More Than One Arrangement

IV.

How To Draw Organic Compounds A. Rules 1. Number of Bonds Carbon - 4 bonds S&O N&P - 2 bonds - 3 bonds

H, Cl, Br, I - 1 bond 2. First Connect Carbons to Carbons 3. Make Certain That Every Carbon Has 4 Bonds 4. Consider Special Arrangements - Functional Groups 5. Begin To Fill In With Atoms 6. Make Certain That O, S, N, Etc. Have Correct Number of Bonds

B.

Kinds of Formulas

1. Molecular

2. Structural Stick

3. Condensed Structural

4. Carbon Skeleton

C.

Examples 1. C4 H 10

2. C5 H12

V.

Functional Groups

A.

Comments 1. All hydrocarbon chains with a given functional group will have a similar set of properties regardless of the number of carbons in the chain.

2.

A hydrocarbon chain with a set number of carbons but containing different functional groups will demonstrate different properties.

3.

Reactions occur at functional groups.

B.

We will examine functional groups made up of

1.

Carbons and Hydrogens

2.

Oxygen & Sulfur

3.

Nitrogen And Phosphorous

VI.

Hydrocarbons - Contain Only C & H

A.

Overview 1. 2. 3. 4. 5. Alkanes Alkenes Alkynes Cyclic Hydrocarbons Aromatic Compounds

B.

General Formulas and Functional Groups 1. Alkanes a. CnH (2n+2) b. C-C

2.

Alkenes a. CnH (2n) b. C = C

3.

Alkynes a. CnH (2n-2) b. C = C

4.

Cyclic Hydrocarbons a. Cycloalkanes - Carbons are arranged in ring but only C - C bonds are present

b. Bridgehead Cycloalkanes

c.

Cycloalkenes - Carbons are arranged in Ring but only C - C bonds except for one C = C bond

5.

Aromatic Compounds - Deal With Later

6.

Heterocylic Compounds - Deal With Later

VII.

Isomerism A. Definitions 1. Two or more carbon compounds can have the same kinds and numbers of atoms, but different arrangements of atoms.

2.

Each unique arrangement of atoms has its own characteristic properties and is called an isomer.

B.

Concepts 1. There are different ways that two structures can differ from one another, hence there are different kinds of isomers. To determine that two compounds are isomers you must: a. Check to see that each structure contains the same number of carbons, hydrogens, etc. as the other compound and

2.

b.

Check to make certain that the two structural stick formulas are different from each other nonsuperimpossible

C.

Alkanes and Chain Isomerism - Differ in the arrangement of carbons in the chain 1. Butanes

2. Pentanes

3. Hexanes

D.

Alkenes & Alkynes and Positional Isomerism - Differ In Location of C=C Or C = C In Chain 1. Butenes

2. Pentenes

3. Hexynes

E.

Alkenes and Geometric Isomerism 1. Due To Lack Of Freedom Of Rotation Around C = C Bond

2.

Example - Two Isomers of 2-butene

3.

Conditions Necessary For Geometric Isomerism

A.

Must have a C=C double bond or ring

B.

Two groups attached to each C of C=C must be different

4.

Cis vs Trans

X \ C = C / \ cis /

X \ / C= C / \ X trans

F.

Chain - Ring Isomerism 1. Hexene vs Cyclohexane CH2=CHCH2 CH2 CH2 CH3

2. Heptene Vs Methylcyclohexane

CH2=CHCH2 CH2 CH2 CH2CH3

CH3 -

G.

Cycloalkanes and Geometric Isomerism 1. Two 1,2-dibromocyclohexanes

2. Two 1,3-dibromocyclohexanes

VIII.

Aromatic Compounds A. Definition and Characteristics 1. Their Formulas They Appear To Be Very Unsaturated, but They React As Though They Are Saturated Hydrocarbons We usually See Them As Six Membered Rings With Alternating Double Bonds or Circle Inside Ring

2.

a. Resonance Structures

b. Resonance Hybrid

B.

Monosubstituted Derivatives of Benzene

C.

Disubstituted Derivatives of Benzene

D.

Polycyclic Aromatics 1. Fused Rings

2. Rings Not Fused

IX.

Heterocyclic Ringed Compounds A. Definition of Heteroatom - Non Carbon Atom That Appears In A Ring Definition of Heterocyclic Compound - Ringed Compound With Non Carbon Atom In The Ring Ring Size

B.

C.

X.

Nomenclature A. B. Common Vs IUPAC First Ten Alkanes - Stem + Ending CH4 - Methane C2H6 - Ethane C3H8 - Propane C4H10 - Butane C5H12 - Pentane C6H14 - Hexane C7H16 - Heptane C8H18 - Octane C9H20 - Nonane C10H22 - Decane

C.

Ending For Alkenes, Alkynes, Cycloalkanes, Aromatics

1.

Alkenes - ene number to locate the C=C

2.

Alkynes -yne

number to locate the C = C

3.

Cyclo (stem) ane

4.

Cyclo (stem) ene

D.

Branched Chains and Nomenclature 1. Find the longest continuous chain, and use that number of carbons to determine the stem. Add the appropriate ending.

a.

If alkene or alkyne requires that the double or triple bond be located with a number How to number the chain

b.

If alkane number the chain so any branches or substituents get the lowest set of numbers

c.

Identify substituents CH3 CH3CH2ClBr INO2methyl ethyl chloro bromo iodo nitro

d.

If more than one substituent, use prefixes 2 = di 3 = tri 4 = tetra 5 = penta 10 = deca 6 = hexa 7 = hepta 8 = octa 9 = nona

e.

List the substituents alphabetically

f.

Locate all substituents

g.

#- methyl #,#-dimethyl #,#,#-trimethyl

E.

Examples C C | | C C C C C C- C

C C | | C = C C C C C- C

C C | | CCCCCC=C

C C | | C C C C C C- C | | C Br | C

XI.

Reactions of Hydrocarbons

A.

Alkanes 1. Relatively Inert

2.

Combustion

CH4 + O2 (plenty) - CO2 + H2O

CH4 + O2 (limiting) C + H2O

3.

Reaction with Cl2 or Br2 in Light h R-H + Br2 -----> HBr + R-Br

R-H + Br2 -----> NR B. Unsaturated Hydrocarbons

1.

Meaning of Unsaturation

Has one or more C = C or C = C s

2.

Combustion C = C or C = C + O2 (plenty) C + H2O

3.

Addition Reactions

a.

Reaction with Br2

Test for Unsaturation

b.

Addition of Hydrogen

4.

Oxidation Reactions

a.

Evidence of Oxidation

Increase in the number of O

Decrease in the number of Hs

Go from C O to C = O

b.

[O] = Oxidizing agents

KMnO4

Cr2O7-2 / H+

CrO3

c.

KMnO4 Rxn for Unsaturation

Alkane + KMnO4 ----->

Alkenes

Alkynes

d.

Observations

Alkanes

Alkene

Alkynes

e.

Baeyer's Test for Unsaturation

Add KmnO4 and observe

Saturated Remains purple

Unsaturated - Purple Brown

C.

Aromatic Hydrocarbons

1.

Combustion

C6H6 + O2 (plenty) C + H2O Burns very sooty

2.

Aromatic Substitution

Br2 +

HBr + Br-

3.

Oxidation with KMnO4 NR

KMnO4 +