Addition polymerisation

This question is about polymers.

A section of the polymer PVC is shown.

Name the monomer used to make PVC.

Draw the structure of the monomer used to make PVC.

Structure

State why PVC is not biodegradable.

Diisobutyl phthalate (DIBP) is a plasticiser added to PVC to modify its properties.

State how the properties of PVC are modified by the addition of DIBP.

An incomplete equation for the reaction used to make DIBP is shown.

Complete the equation.

Give the name of the mechanism for this reaction.

Deduce the empirical formula of DIBP.

Empirical formula of DIBP

A different plasticiser, DEHA, is added to PVC used for food packaging.

The structure of DEHA is

Identify the organic compound that would react with hexanedioic acid to form DEHA.

DEHA can be absorbed into food from PVC packaging.

In an investigation, 1 kg samples of three different foods are stored in PVC packaging for 30 days.

Table 1 shows the water content, fat content and mass of DEHA in each type of food after 30 days.

Use your knowledge of intermolecular forces to explain these results.

The polymer nylon 6,6 can be made from hexanedioyl dichloride and hexane-1,6-diamine.

Figure 2 shows an incomplete mechanism for the first steps in this reaction.

Draw the missing intermediate in the box in Figure 2.

Complete Figure 2 by adding the curly arrows and any relevant lone pairs of electrons involved in these steps in the mechanism.

The polymer nylon 6 can be made by heating caprolactam with water.

Figure 3 shows the species involved in the first three steps of the mechanism for this reaction.

Complete Figure 3 by adding the curly arrows and any relevant lone pairs of electrons involved in these steps in the mechanism.

This question is about 2-methylbut-1-ene.

Name the mechanism for the reaction of 2-methylbut-1-ene with concentrated sulfuric acid.

Outline the mechanism for this reaction to form the major product.

Outline of mechanism to form major product

Draw the structure of the minor product formed in the reaction in Question 03.1

Explain why this is the minor product.

Structure of minor product

Draw the skeletal formula of a functional group isomer of 2-methylbut-1-ene.

2-methylbut-1-ene can form a polymer.

State the type of polymerisation.

Draw the repeating unit for the polymer formed.

Type of polymerisation

Repeating unit

State the type of reaction in step 1.

Identify the reagent(s) and conditions needed for step 1.

State the name of the mechanism for the reaction in step 2.

Identify the inorganic reagent needed for step 2.

Name the organic product of step 2.

Name of mechanism

Name of organic product

The organic product of step 2 is reacted with concentrated sulfuric acid in step 3.

Outline the mechanism for step 3.

Draw the repeating unit of polystyrene.

The outer layers of some golf balls are made from a polymer called polyisoprene. The isoprene monomer is a non-cyclic branched hydrocarbon that contains 88.2 % carbon by mass. The empirical formula of isoprene is the same as its molecular formula.

Deduce the molecular formula of isoprene and suggest a possible structure.

Molecular formula

Structure

The insides of some golf balls are made from a mixture of three other polymers. The repeating unit for one of these polymers is shown.

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

Give the IUPAC name of the monomer.

Skeletal formula of monomer

A second polymer in the mixture has a repeating unit with the structure shown.

The third polymer in the mixture is a stereoisomer of this polymer.

Draw the structure of the repeating unit of the third polymer.

Give a reason why this type of stereoisomerism arises.

Repeating unit

Golf balls recovered from lakes and ponds can be used again even after being in water for several years.

Explain why these golf balls do not biodegrade.

Ethanal reacts with potassium cyanide, followed by dilute acid, to form 2-hydroxypropanenitrile.

Name the mechanism for the reaction between potassium cyanide and ethanal.

The 2-hydroxypropanenitrile formed by the reaction in question 04.1 is a mixture of equal amounts of two isomers.

State the name of this type of mixture.

Explain how the structure of ethanal leads to the formation of two isomers.

Draw 3D representations of the two isomers to show the relationship between them.

3D representations

2-Hydroxypropanenitrile can be used in the synthesis of the monomer,

Suggest a suitable reagent and conditions for the conversion of 2-hydroxypropanenitrile into acrylonitrile.

Draw a section of the polymer polyacrylonitrile, showing three repeating units.

Give the full IUPAC name of isomer P.

A sample of P was mixed with an excess of oxygen and the mixture ignited. After cooling to the original temperature, the total volume of gas remaining was

When this gas mixture was passed through aqueous sodium hydroxide, the carbon dioxide reacted and the volume of gas decreased to 155 cm³

Both gas volumes were measured at 25 °C and 105 kPa

Write an equation for the combustion of P in an excess of oxygen and calculate the mass, in mg, of P used.

The gas constant R = 8.31 J K⁻¹ mol⁻¹

Mass of P used mg

Isomer Q (C₆H₁₀O₂) is a cyclic compound. The infrared spectrum of Q is shown in Figure 4 and the¹³C NMR spectrum of Q is shown in Figure 5.

Use these spectra and Tables A and C in the Data Booklet to deduce the structure of Q. In your answer, state one piece of evidence you have used from each spectrum.

Structure of Q.

Evidence from Figure 4

Evidence from Figure 5

Isomers R and S are shown.

Although the¹³C spectra of R and S both show the same number of peaks, the spectra can be used to distinguish between the isomers.

Justify this statement using Table C from the Data Booklet.

Give the number of peaks for each isomer.

Justification

Although the¹H spectra of R and S both show the same number of peaks, the spectra can be used to distinguish between the isomers.

Justify this statement using the splitting patterns of the peaks.

Give the number of peaks for each isomer.

Justification

The action of heat on 5-hydroxyhexanoic acid can lead to two different products.

On gentle heating, 5-hydroxyhexanoic acid loses water to form a cyclic

Under different conditions, 5-hydroxyhexanoic acid forms a polyester.

Draw the structure of T.

Draw the repeating unit of the polyester and name the type of polymerisation.

Structure of T

Repeating unit of polyester

Type of polymerisation

Isomer U is shown.

The polymer formed by U and the polymer formed by 5-hydroxyhexanoic acid in Question 10.6 both contain ester groups that can be hydrolysed.

Draw the repeating unit of the polymer formed by U.

Justify the statement that, although both polymer structures contain ester groups, the polymer formed by U is not biodegradable.

Repeating unit of polymer formed by U.

Justification