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

Reactant #1
Alkene

Amine

Carboxylic
acid

Reactant #2
Pd/C + H2

Product
Alkane

Acid

Ammonium
salt

Base

Example
H

NH2

Salt
(Carboxylate Ph
salt)

Ester

Ester

Alcohol,
acid, heat

Ester

Water,
acid, heat

Carboxylic
acid

Water,
base

Carboxylic
acid

OH

O
R

O
R

Water, acid

Alcohol

CH2

Alkene

Alcohol

Strong acid

Alkyl
halide

Br2

Dibromide

OH

OH

Carboxylic acid
(primary alcohol)

Alkane

Cl2, h
(or peroxides)

Benzene
derivative

Br2, FeCl3

C
H2

C
H2

proceeds through carbocation

halide adds to most
substituted carbon
(Markovnikoff rule)

Br
H
R

proceeds through carbocation

Br

K2CrO7

OH

KMnO4

R
Cl
R

Br2, FeBr3

Cl

"Oxidant"

CCl3

R-SH

(number of new CCl

bonds depends on
# of equivalents)

Br

+
O

2nd weakest

Increases as electronegativity
difference increases
3rd greatest for effect on water
solubilty and boiling points

Name

Weakest

Increases with surface area

(increasing length of carbon
chains)

Name

Alkyl

Eth-

OH

Hydroxyl

OH

Pentanol or pentyl alcohol

Prop-

But-

Cl, Br, F, I

Halide

Cl

Pentyl chloride

Pent-

NH2

Amine

NH2

Pentylamine

Hex-

Ether

Pentyl methyl ether

HeptThiol

SH

Pentane thiol

Oct-

Non-

Example

Dec-

Alkene

Pentene
O

Aldehyde

R C H
O
R C R
O

Secondary: attached to TWO

carbon atoms

R C OH

Pentanal

O
Ketone
Me

Butyl methyl ketone

OR 2-pentanone

O
Carboxylic
acid

Pentanoic acid
OH

R C OR

Quaternary: attached to FOUR

carbon atoms

Name
Pentane

Primary carbon: attached to ONE

carbon atom

Ester

OMe

Methyl pentanoate

O
Amide

R C NH2

Also gives 1,4 (para) product

but never 1,3 (meta) product

Br

Phenyl
RSSR

2nd greatest for effect on

water solubility and boiling
points

N-methyl pentamide
NHMe

Other important nomenclature terms to remember

Aryl bromide

Disulfide

Free-radical reaction

2nd strongest

Functional Group

Root

Tertiary: attached to THREE

carbon atoms

OH

[ox]
Thiol

Note that secondary alcohols

stop at the ketone stage

Meth-

10-

gives rise to greatest water

solubility (most polar)
also highest boiling points

# Carbons

K2CrO7

Strongest

Notes

worst for water solubility

(least polar)
best for solubility in non-polar
solvents (e.g. pentane)

SH
O

Van Der Waals

(London forces)

Hydrocarbons

Strength

O
H
H

ketones, aldehydes,
esters, alkyl halides,
etc. - any molecule
with a strongly
electronegative
element (O, N, F, Cl, Br)

Attraction between
temporary dipoles

Results in trans product

Me

alcohol forms on most

substituted carbon
(Markovnikoff rule)

R Cl

Cl2, h
Alkyl chloride

NH4 Cl

Water, alcohols
carboxylic acids
amides, amines

Attraction between
dipole moments
caused by differences
in electronegativity

DipoleDipole

This is called ester hydrolysis

or saponification

OH

R OH

H2O

OH

H2O

OH

Salts

This is the reverse of the

above reaction.

NaOH

Br2

Alcohols used as solvent

Here we use water as solvent.

H2O

KMnO4

H2SO4,

CH2

Alcohol

OMe

HCl

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

K2CrO7

H2SO4,

H2O

Example

Attraction between
positively charged H
and negatively charged
O, N or F.

Hydrogen
Bonding

HCl

R
Alkene

O EtNH3

H2O
OMe

Ph

H2O
OMe

Attraction
between
point charges

Ionic

Found in

MeOH
OH

amines but NOT amides

(amides are not basic on nitrogen)

NH3Cl

Type of
Interaction

Name

EtNH2

R
Alkene

Boiling point increases with strength of the

intermolecular interactions.
Water solubility increases with polarity.

The Four Types of Intermolecular Bonding in Organic Chemistry

cis addition (hydrogens go

on same side of alkene)

HCl

O
Carboxylic
acid

Notes
HH HH

Pd/C, H2

http://masterorganicchemistry.com

(e.g. phenyl
bromide)

OH
isopropyl
e.g. isopropanol

Copyright 2012
James A.Ashenhurst
Aug 2012, version 1.1
james@masterorganicchemistry
.com

R
Trans

Cis
1,2
ortho

1,3
meta

1,4
para