Haloalkanes

This video looks at the preparation and purification of a primary haloalkane (1-bromobutane) from the corresponding primary alcohol (butan-1-ol). This has an Sn2 mechanism. You will find an accompanying video (Haloalkanes 4) that looks at the preparation of a tertiary haloalkane in a Sn1 mechanism.

This video outlines the mechanisms of Sn1 and Sn2 nucleophilic substitution reactions of haloalkanes and explains why primary haloalkanes do not undergo Sn1 using a reaction profile diagram

One in a series looking at the chemistry of haloalkanes (alkyl halides). This video looks at the reaction of bromoethane with an ethanolic solution of potassium hydroxide. The contrast is drawn between nucleophilic substitution and elimination mechanisms. In substitution the hydroxide ions behave as nucleophiles, whereas in elimination, the hydroxide ions act as a Bronsted base bringing about deprotonation.

This video both demonstrates and explains the factors that control the rate of hydrolysis of haloalkanes. 1-chlorobutane should be more reactive than 1-iodobutane, on the basis that the C-Cl bond is more polar than the C-I bond - thus attracting the nucleophile better. However, 1-iodobutane would be expected to react faster on the basis that the C-I bond is weaker than the C-Cl bond, thus lowering the activation energy of the reaction. This video identifies which of the two factors has the greater influence on the rate.

One in a series of videos on haloalkanes (alkyl halides), it looks at the structures and names of the 11 isomers of bromopentane (C5H11Br). That includes both structural and optical isomers.

One in a series of videos on haloalkanes (alkyl halides), it looks at the structures and names of the 26 isomers of bromohexane (C6H13Br). That includes both structural and optical isomers.

This video discusses the trends in boiling points of haloalkanes, in terms of how the chain length and specific halogen atom present, influence the intermolecular forces between the molecules.

This video looks at three common nucleophilic substitution reactions of haloalkanes. The reaction with aqueous sodium hydroxide, ammonia in water or alcohol and potassium cyanide in a mixture of water and alcohol. The mechanism common to these reactions is considered in detail.