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

Reactant #1 Alkene Reactant #2 Pd/C + H2 Product Alkane H R Amine Acid Ammonium salt Salt (Carboxylate salt) Ester H R HCl R NH2 O Carboxylic acid Base Ph O Carboxylic acid Alcohol, acid, heat R OH OH MeOH H2SO4, R EtNH2 Ph R O O EtNH3 O OMe We use the alcohol as solvent. Hydrogen Bonding Attraction between positively charged H and negatively charged O, N or F. Water, alcohols carboxylic acids amides, amines + O H H H O H + O + 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

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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 boling points

Name

Type of Interaction Attraction between point charges

Found in Salts

Example NH4 Cl

Ionic

2nd strongest

2nd greatest for effect on water solubility and boiling points

O 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. 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)

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 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

2 3 4 5

Alkene

Br2

Dibromide

Br2

Br H R R R

Results in trans product

6 7

Br

Alcohol

K2CrO7

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

OH

K2CrO7 H2O

SH O OH 8 9 10O R Note that secondary alcohols stop at the ketone stage Primary: attached to ONE carbon atom O OH Secondary: attached to TWO carbon atoms Free-radical reaction (number of new CCl bonds depends on # of equivalents) Also gives 1,4 (para) product but never 1,3 (meta) product Tertiary: attached to THREE carbon atoms Quaternary: attached to FOUR carbon atoms OctNonDecC O R C H O R C R O R C OH O R C OR O R C NH2 Other important things to remember: 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

OH

K2CrO7 H2O R

Me O Carboxylic acid O Ester O Amide NHMe OMe OH

Alcohol

KMnO4

Carboxylic acid (primary alcohol)

OH

KMnO4 H2O Cl2, h R

Cl R

Cl CCl3

Alkane

Cl2, h (or peroxides)

Alkyl chloride

Methyl pentanoate N-methyl pentamide

Me

R Benzene derivative Br2, FeCl3 Aryl bromide

Br2, FeBr3

R Br

[ox] Thiol "Oxidant" Disulfide R-SH RSSR Phenyl (e.g. phenyl bromide)

Copyright 2010 James A Ashenhurst May 2010, version 1.0 james@writechem.com 1,2 ortho 1,3 meta

1,4 para