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4.2.1 Alcohols Quiz

a. The controlled catalysed reaction of ethene with oxygen forms epoxyethane as the only product.

i. Write an equation for this reaction.

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ii. When burnt in excess oxygen, ethene completely combusts.

Write the equation for the complete combustion of ethene.

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b. Epoxyethane reacts with water in the presence of an acid catalyst to form ethane-1,2-diol.
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i. Draw the dipoles on the carbon and oxygen atoms on the displayed formula of epoxyethane.

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ii. The mechanism uses the ‘curly arrow’ model.

What does a ‘curly arrow’ represent?

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iii. What type of bond fission occurs in step 2?

Explain your answer.

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iv. How can you tell that water is behaving as a nucleophile in step 3?

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v. How does the mechanism show that H+ ions act as a catalyst in this reaction?

Refer to the steps in the mechanism in your answer.

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vi. Epoxyethane reacts with methanol, CH3OH, to form a compound with the molecular formula C3H8O2.

Suggest the structure of this compound.

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c. Ethane-1,2-diol is much less volatile than ethanol.

Suggest why.

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d. Ethane-1,2-diol reacts with warm acidified potassium dichromate(VI). A number of different organic products
are formed.

Draw the displayed formulae of two of these organic products.

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2. Pentan-2-ol, shown below, is a secondary alcohol.

a. Pentan-2-ol can be converted into three alkenes, A, B and C, by the elimination of water.

 Two of the alkenes, A and B, are stereoisomers.

 The third alkene, C, is a structural isomer of both A and B.

This elimination often uses a catalyst.

i. What is a suitable catalyst for this reaction?

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ii. Construct an equation, using molecular formulae, for the elimination of water from pentan-2-ol.

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iii. Explain what is meant by the terms structural isomers and stereoisomers.

Structural isomers

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Stereoisomers

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 iv. In the boxes below:

 Draw the structures of stereoisomers A and B.

 Draw the structure of isomer C.

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v. Stereoisomers A and B show E/Z isomerism.

State two features of these molecules that enable them to show E/Z isomerism.

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b. Pentan-2-ol can be oxidised by heating under reflux with acidified aqueous potassium dichromate(VI).

Complete the equation for this oxidation.

Use skeletal formula for the organic product

Use [O] to represent the oxidising agent.

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c. Pentan-1-ol can also be oxidised but it gives two different products.

Complete the flow chart below to show the structures of the two organic products formed.

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