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Organic Ahl (HL Only) Qs 1

1. Propene reacts with hydrogen chloride to form 2-chloropropane via an electrophilic addition reaction. 2-Chloropropane can be converted to propan-2-ol using sodium hydroxide. Propan-2-ol can also be made from propanone using an acid-catalyzed hydration reaction. 2. 2-Bromobutane exhibits optical isomerism with two stereoisomers that can be distinguished using a polarimeter. It undergoes an SN1 reaction with hydroxide ion in a polar protic solvent to form the racemic product. 3. Benzene undergoes nitration to form nitrobenzene using nitric and

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32 views4 pages

Organic Ahl (HL Only) Qs 1

1. Propene reacts with hydrogen chloride to form 2-chloropropane via an electrophilic addition reaction. 2-Chloropropane can be converted to propan-2-ol using sodium hydroxide. Propan-2-ol can also be made from propanone using an acid-catalyzed hydration reaction. 2. 2-Bromobutane exhibits optical isomerism with two stereoisomers that can be distinguished using a polarimeter. It undergoes an SN1 reaction with hydroxide ion in a polar protic solvent to form the racemic product. 3. Benzene undergoes nitration to form nitrobenzene using nitric and

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ORGANIC CHEMISTRY AHL (HL only)

Please ensure that you have also completed the Core (SL & HL) questions

1. (a) Propene (CH3CHCH2) reacts readily with hydrogen chloride in an electrophilic addition
reaction. The major organic product is 2-chloropropane.

(i) Sketch the mechanism for the reaction of propene with hydrogen chloride using curly arrows.
[4]

(ii) Explain why the major organic product is 2-chloropropane.


[2]

…………………………………………………………………………………………………………………………………………………………
…………………………………………………………………………………………………………………………………………………………
…………………………………………………………………………………………………………………………………………………………

(iii) State the reagent needed to convert 2-chloropropane into propan-2-ol.


[1]

…………………………………………………………………………………………………………………………………………………………

(iv) Propan-2-ol can also be made from propanone (CH3COCH3). State the type of reaction, and the
reagents needed for the conversion.
[3]

Type of reaction:………………………………………………………………………………………………………………………………
Reagents:…………………………………………………………………………………………………………………………………………
…………………………………………………………………………………………………………………………………………………………
2. (a) 2-bromobutane exhibits optical isomerism.

(i) Draw the two stereoisomers for 2-bromobutane using wedge-dash type representations.
[2]

(ii) Outline how two enantiomers can be distinguished using a polarimeter.


[2]

…………………………………………………………………………………………………………………………………………………………
…………………………………………………………………………………………………………………………………………………………
…………………………………………………………………………………………………………………………………………………………
…………………………………………………………………………………………………………………………………………………………

(b) 2-bromobutane undergoes an SN1 mechanism with a hydroxide ion in a polar protic solvent.

(i) Sketch the mechanism for the SN1 reaction of 2-bromobutane with a hydroxide ion using curly
arrows.
[3]

(ii) Name a suitable polar protic solvent.


[1]

…………………………………………………………………………………………………………………………………………………………
(iii) State the meaning of each of the three terms in SN1.
[2]

…………………………………………………………………………………………………………………………………………………………
…………………………………………………………………………………………………………………………………………………………

(iv) The 2-bromobutane used in the reaction in 2(b) above consisted of a single enantiomer. State
the enantiomeric nature of the product of the reaction. Explain your answer.
[2]

…………………………………………………………………………………………………………………………………………………………
…………………………………………………………………………………………………………………………………………………………
…………………………………………………………………………………………………………………………………………………………

3. (a) Benzene will undergo nitration when exposed to a nitrating mixture. If the temperature is
kept below 50°C mono-nitration will occur.

(i) Write the equation to produce the active nitrating agent from concentrated sulfuric and nitric
acids.
[1]

…………………………………………………………………………………………………………………………………………………………

(ii) Sketch the mechanism for the nitration of benzene, using curly arrows.
[3]

(iii) State the role of the sulfuric acid.


[1]

…………………………………………………………………………………………………………………………………………………………
…………………………………………………………………………………………………………………………………………………………
(iv) What does a double-headed curly arrow represent?
[1]

…………………………………………………………………………………………………………………………………………………………
…………………………………………………………………………………………………………………………………………………………

(v) Nitrobenzene, C6H5NO2, can be converted to phenylamine via a two-stage reaction.

In the first stage, nitrobenzene is reduced with tin in an acidic solution to form an intermediate
ion and tin(II) ions. In the second stage, the intermediate ion is converted to phenylamine in the
presence of hydroxide ions.

Formulate the equation for each stage of the reaction


[2]

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…………………………………………………………………………………………………………………………………………………………
…………………………………………………………………………………………………………………………………………………………
…………………………………………………………………………………………………………………………………………………………

4. E/Z isomerism is exhibited by the molecule, M:

(a) Determine which isomer is shown above. Explain your answer.


[1]

…………………………………………………………………………………………………………………………………………………………
…………………………………………………………………………………………………………………………………………………………
…………………………………………………………………………………………………………………………………………………………

(b) Use your answer in 4(a) to determine the full IUPAC name for molecule, M.
[1]

…………………………………………………………………………………………………………………………………………………………

Total Marks 32 (48 minutes)

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