11 mark
Which of these reactions does not result in the formation of a racemic mixture?
but-2-ene with HCl
but-1-ene with HCl
propanal with HCN
propanone with HCN
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4.6 Organic Chemistry: Chirality
21 mark
When a single enantiomer of 2-iodobutane reacts with sodium hydroxide, the product is a mixture of enantiomers. This is because
the reaction is a nucleophilic substitution
the reaction proceeds via a negatively charged transition state
the reaction proceeds via a carbocation intermediate
the reaction rate depends on the concentration of 2-iodobutane
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31 mark
A sample of a bromoalkane, RBr, containing a single optical isomer reacts with hydroxide ions in an SN1 mechanism.
RBr + OH− format('truetype')%3Bfont-weight%3Anormal%3Bfont-style%3Anormal%3B%7D%3C%2Fstyle%3E%3C%2Fdefs%3E%3Ctext%20font-family%3D%22math12bba9f4124283edd644799e0ce%22%20font-size%3D%2216%22%20text-anchor%3D%22middle%22%20x%3D%2210.5%22%20y%3D%2216%22%3E%26%23x2192%3B%3C%2Ftext%3E%3C%2Fsvg%3E)
ROH + Br−
The alcohol formed is a racemic mixture.
From this information, it can be deduced that RBr is most likely to be
primary only
secondary only
tertiary only
primary, secondary or tertiary
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41 mark
Which of these structures is not identical to the others?
Structure A
Structure B
Structure C
Structure D
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11 mark
Menthol has a number of medicinal uses. It can be extracted from the peppermint plant.
The structure of menthol is
How many chiral centres are there in one molecule of menthol?
1
2
3
4
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21 mark
Citronellol is found in rose and geranium oils.
The type(s) of stereoisomerism shown by citronellol is
optical and geometric isomerism
optical isomerism only
geometric isomerism only
neither optical nor geometric isomerism
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31 mark
How many optical isomers does this molecule have?
2
3
6
8
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