Introduction to Organic Chemistry

Explain the meaning of the term structural isomerism.

Explain the meaning of the term stereoisomerism.

Give two reasons why pent-1-ene does not show stereoisomerism.

A structural isomer of pent-1-ene is used as the monomer to form a polymer. The repeat unit of this polymer is shown.

Draw the displayed formula of the monomer used to make this polymer.

Give the name of the monomer.

A different structural isomer of pent-1-ene shows geometrical isomerism.

Draw the structure of one of the two geometrical isomers with the formula $\text{C}_5\text{H}_{10}$.

Give the full name of this isomer.

Give the structures of a pair of positional isomers with the formula C₄H₈.

Give the structures of a pair of chain isomers with the formula C₄H₈, that do not exhibit stereoisomerism.

Give the structures and full names of a pair of stereoisomers with the formula C₄H₈.

The structure of a molecule, A, of formula C₄H₈ is shown.

Draw a functional group isomer of molecule A in box B. Explain how molecules A and B could be distinguished by a chemical test.

Suggest possible structural formulae for H, J and K.

Three structural formulae are possible for H but only one for J and one for K.

Draw the displayed formulae of those isomers which show cis-trans isomerism.

Draw the displayed formulae of those isomers which are chiral, indicating in each case the chiral carbon atom with an asterisk (*).

Explain the meaning of the term nucleophile and identify the species which acts as the nucleophile during this reaction.

species acting as nucleophile ....................................................................................................

Name the type of stereoisomerism shown by $\text{CH}_3\text{CH(OH)CN}$.

Draw three-dimensional diagrams of this pair of stereoisomers.

Indicate with an asterisk (*) the chiral centre on one of the structures drawn.

Give the skeletal formula for each of the four alcohols and complete the diagram with the names of the types of structural isomerism shown by each linked pair of compounds.

State which of these two isomers shows stereoisomerism. Explain why this molecule is capable of showing stereoisomerism.

Draw displayed formulae to show the two stereoisomers.

In the boxes below, draw the structural formulae of four isomers with this formula that are esters.

Which, if any, of your esters, W, X, Y or Z, is chiral?

Using the terms mentioned above, state as clearly as you can the nature of each of the following reactions.

reaction 1 .......................................................................

reaction 2 .......................................................................

one substance that behaves as an electrophile

reaction....... electrophile

What is meant by the term nucleophile?

Reactions 3 and 4 involve nucleophiles.

For each reaction, give the formula of the nucleophile.

reaction 3

reaction 4

Give the structural formulae of P, Q, R and S.

P .................................................................... Q .....................................................................

R .................................................................... S .....................................................................

Explain what is meant by the term stereoisomerism.

Draw the displayed formulae of the geometrical isomers of R and name them both.

name ........................................................ name .........................................................