Summary Sheet - Introduction to Chemical Reactivity, Nomenclature, Boiling Points, and Water Solubility

Reactant #1 Alkene Reactant #2 Pd/C + H2 Product Alkane H R Amine Acid Ammonium salt H R HCl R NH2 O Carboxylic acid Base Salt (Carboxylate Ph salt) O Carboxylic acid Alcohol, acid, heat Ester R OH OH MeOH H2SO4, R EtNH2 Ph R O O EtNH3 O OMe Alcohols used as solvent Hydrogen Bonding Attraction between positively charged H and negatively charged O, N or F. Water, alcohols carboxylic acids amides, amines NH3Cl Example Pd/C, H2 HH HH R R Notes cis addition (hydrogens go on same side of alkene) amines but NOT amides (amides are not basic on nitrogen) The Four Types of Intermolecular Bonding in Organic Chemistry Type of Interaction Attraction between point charges

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Boiling point increases with strength of the intermolecular interactions. Water solubility increases with polarity. Strength Strongest Notes gives rise to greatest water solubility (most polar) also highest boiling points

Name

Found in Salts

Example NH4 Cl + H O H

Ionic

O H H + O +

2nd strongest

2nd greatest for effect on water solubility and boiling points

O Attraction between dipole moments caused by differences in electronegativity ketones, aldehydes, esters, alkyl halides, etc. - any molecule with a strongly electronegative element (O, N, F, Cl, Br)

Ester

Water, acid, heat

Carboxylic acid

O R OMe

H2O H2SO4, R

O OH

This is the reverse of the above reaction. Here we use water as solvent.

DipoleDipole

2nd weakest

Increases as electronegativity difference increases 3rd greatest for effect on water solubilty and boiling points Increases with surface area (increasing length of carbon chains) worst for water solubility (least polar) best for solubility in non-polar solvents (e.g. pentane)

Ester

Water, base

Carboxylic acid

O R OMe

H2O NaOH R

O OH

This is called ester hydrolysis or saponification

Van Der Waals (London forces)

Attraction between temporary dipoles

Hydrocarbons

Name

Weakest

R Alkene Water, acid Alcohol R CH2

HCl H2O R

R OH C H2 R Cl R C H2 H H

alcohol forms on most substituted carbon (Markovnikoff rule) proceeds through carbocation halide adds to most substituted carbon (Markovnikoff rule) proceeds through carbocation

# Carbons 1 2

Root MethEthPropButPentHexHept-

Functional Group R OH Cl, Br, F, I NH2 R O R

Name Alkyl Hydroxyl Halide Amine Ether

Example

Name Pentane OH Cl NH2 O SH Pentanol or pentyl alcohol Pentyl chloride Pentylamine Pentyl methyl ether

R Alkene Strong acid Alkyl halide R CH2

HCl

3 4 5

Alkene

Br2

Dibromide

Br2

Br H R

6 H Results in trans product 7 8 O OH 9 10Note that secondary alcohols stop at the ketone stage

Br R R

SH OctNonDecC O R C H O R C R O R C OH O R C OR O R C NH2 Other important nomenclature terms to remember Br Also gives 1,4 (para) product but never 1,3 (meta) product Phenyl Br OH isopropyl e.g. isopropanol R Trans Cis R R R C

Thiol Alkene O Aldehyde O Ketone H

Pentane thiol Pentene Pentanal Butyl methyl ketone OR 2-pentanone Pentanoic acid

Alcohol

K2CrO7

Carboxylic acid R (primary alcohol) OR ketone (secondary alcohol) R R

OH

K2CrO7 H2O

OH

K2CrO7 H2O R

R O R R R Cl R O OH Cl CCl3 Free-radical reaction (number of new CCl bonds depends on # of equivalents) Primary carbon: attached to ONE carbon atom Secondary: attached to TWO carbon atoms Tertiary: attached to THREE carbon atoms Quaternary: attached to FOUR carbon atoms

Me O Carboxylic acid O Ester O Amide NHMe OMe OH

Alcohol

KMnO4

Carboxylic acid (primary alcohol)

OH

KMnO4 H2O Cl2, h

Methyl pentanoate N-methyl pentamide

Alkane

Cl2, h (or peroxides)

Alkyl chloride

Me

R Benzene derivative Br2, FeCl3 Aryl bromide

Br2, FeBr3

Copyright 2012 James A.Ashenhurst Aug 2012, version 1.1 james@masterorganicchemistry .com 1,2 ortho 1,3 meta 1,4 para

[ox] Thiol "Oxidant" Disulfide R-SH RSSR

(e.g. phenyl bromide)