11 mark
The structures of two isomers are shown.
What kind of isomerism is shown by these molecules?
| ☐ | A | carbon chain | |
| ☐ | B | positional | |
| ☐ | C | E/Z | |
| ☐ | D | cis/trans |
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3.1 Introduction to Organic Chemistry
2a2 marks
This question is about alcohols and their reactions.
The table gives some of the names and skeletal formulae of isomers having the formula C4H9OH.
Complete the table.
2b6 marks
i)
Some alcohols react with concentrated phosphoric acid to form alkenes.
What is the type of this reaction?
What is the type of this reaction?
(1)
| ☐ | A | addition | |
| ☐ | B | elimination | |
| ☐ | C | oxidation | |
| ☐ | D | substitution |
ii)
When butan‐2‐ol reacts with concentrated phosphoric acid, two stereoisomers are formed.
Explain what is meant by the term stereoisomers.
(2)
iii)
Draw the structures and give the names of the two stereoisomers.
(2)
iv)
Name this type of stereoisomerism.
(1)
2c1 mark
2‐methylpropan‐2‐ol may be formed by the reaction between 2‐bromo‐2‐methylpropane and aqueous potassium hydroxide.
What is the role of the hydroxide ions in this reaction?
| ☐ | A | alkali | |
| ☐ | B | catalyst | |
| ☐ | C | electrophile | |
| ☐ | D | nucleophile |
2d4 marks
i)
CH3CH2CH2CH2OH reacts with the oxidising agent potassium dichromate(VI) in dilute sulfuric acid.
Two organic products can be formed, depending on the conditions.
Write a balanced equation for the formation of one of these products, giving its name and the condition required to achieve this product in high yield.
Use [O] in the equation to represent each oxygen atom from the oxidising agent.
(3)
Equation
Name
Condition
ii)
The colour of the solution at the end of the reaction in (d)(i) will be
(1)
| ☐ | A | brown | |
| ☐ | B | green | |
| ☐ | C | orange | |
| ☐ | D | yellow |
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3a3 marks
This question is about organic compounds.
Organic compounds can be grouped together in homologous series.
i)
Describe two characteristics of a homologous series.
(2)
ii)
Name the homologous series to which propene belongs.
(1)
3b2 marks
Propene can be converted into a mixture of 1-chloropropane and 2-chloropropane, in which 2-chloropropane is the major product.
i)
Give the reagent required for this reaction.
(1)
ii)
What is the type and mechanism of the reaction in (b)(i)?
(1)
| ☐ | A | electrophilic addition | |
| ☐ | B | nucleophilic addition | |
| ☐ | C | electrophilic substitution | |
| ☐ | D | nucleophilic substitution |
3c5 marks
1-chloropropane and 2-chloropropane can be converted into compounds containing the nitrile functional group.
i)
Under appropriate conditions, 1-chloropropane can be converted into butanenitrile, CH3CH2CH2CN.
Which is the reagent for this conversion?
(1)
| ☐ | A | ammonia | |
| ☐ | B | nitric acid | |
| ☐ | C | potassium cyanide | |
| ☐ | D | silver nitrate |
ii)
Under appropriate conditions, 2-chloropropane can be converted into a structural isomer of butanenitrile.
State what is meant by the term ‘structural isomer’.
(2)
iii)
Give the displayed formula and systematic name of the isomer of butanenitrile formed in (c)(ii). You must show all the bonds.
(2)
Displayed formula
Name
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41 mark
What is the systematic name for tiglic acid?
| ☐ | A | E-2-methylbut-2-enoic acid | |
| ☐ | B | Z-2-methylbut-2-enoic acid | |
| ☐ | C | E-3-methylbut-2-enoic acid | |
| ☐ | D | Z-3-methylbut-2-enoic acid |
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