Unit 1 Organic questions

Q1.
The alkene but-1-ene reacts with HBr to form a mixture of 1-bromobutane and
2-bromobutane.

(a) Name and outline the mechanism to form 2-bromobutane in this reaction.

Name of mechanism _____________________________________________

Mechanism

(5)

(b) 15.96 g of but-1-ene reacted to form a mixture of 1-bromobutane and

2-bromobutane.
The mixture formed contained 6.88 g of 1-bromobutane.

Calculate the maximum amount, in moles, of 2-bromobutane that could be formed.

Amount ____________________ mol

(3)

(c) Explain why 2-bromobutane is the major product of this reaction.

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 ___________________________________________________________________

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(2)
(Total 10 marks)

Q2.
Compounds with carbon–carbon double bonds are useful as they take part in a wide
variety of reactions.

(a) 2-Methylpropene reacts with hydrogen bromide to form 2-bromo-2-methylpropane.

Name and outline the mechanism to show the formation of

2-bromo-2-methylpropane from 2-methylpropene.

Name of mechanism _________________________________________________

Mechanism

(5)

(b) In the reaction in part (a), small amounts of 1-bromo-2-methylpropane are also
formed.

Explain why 2-bromo-2-methylpropane is the major product.

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(2)

(c) Draw the displayed formula of a functional group isomer of 2-methylpropene.

(1)

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 (d) 2-Methylpropene forms a polymer that is used in chewing gum.

Give the repeating unit of the polymer formed from 2-methylpropene.

State the IUPAC name of the polymer.

Repeating unit

Name of polymer _________________________________________________

(2)

(e) Explain why the polymer in chewing gum is unreactive.

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(2)
(Total 12 marks)

Q3.
The structure shows a section of a polymer chain formed from the random polymerisation
of two different monomers.

Which pair of monomers could produce this polymer?

A CH2=C(CH3)Cl and CHCl=CHCl

B CH2=C(CH3)Cl and (CH3)2C=C(CH3)2

C (CH3)2C=CH2 and CH2=C(CH3)Cl

D (CH3)2C=CH2 and CHCl=C(CH3)Cl

(Total 1 mark)

Q4.
Which structure shows an E- isomer?

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 A

(Total 1 mark)

Q5.
The molecular formula C5H10 represents several different isomers.

(a) The table below contains information about three isomers of C5H10

Isomer Name Skeletal formula

X Pent-1-ene

Complete the table above for the three isomers of C5H10

(3)

(b) Describe a chemical test to distinguish between isomer Y and isomer Z.

State what would be observed with each isomer.

Test ______________________________________________________________

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 Observation with Y _______________________________________________

Observation with Z _______________________________________________

(3)

(c) Pent-2-ene shows E–Z isomerism.

Draw the skeletal formula of E-pent-2-ene.
Justify your answer using Cahn-Ingold-Prelog (CIP) priority rules.

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(3)

(d) State why pent-1-ene does not show E–Z isomerism.

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(1)
(Total 10 marks)

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