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Edexcel - IAS - Organic Chemistry - 1
Edexcel - IAS - Organic Chemistry - 1
Organic Chemistry_Worksheet_1
Section A
1 Four organic reactions are given below:
3 The compound
5 Which of these compounds would not react when heated with a mixture of
potassium dichromate(VI) and sulfuric acid?
(b) Which of the following shows the correct electron-pair movements in this
reaction?
14 Nucleophiles are
15
The systematic name of the compound with skeletal formula shown above is
22
C2H5Br + NaOH
→ C2H4 + NaBr + H2O
This reaction is an example of
(a) Which of the above bromoalkanes is not a structural isomer of the others?
26
29 Electrophiles are
31 This question is about two isomeric alcohols and two isomeric carbonyl
compounds.
(a) Which of these compounds would not produce a colour change when
heated with acidified sodium dichromate(VI) solution?
Section B
Q1.
Butan-1-ol and three other alcohols, X, Y and Z, are isomers.
(a) Isomer X does not react with a mixture of potassium dichromate(VI) and
sulfuric acid.
Draw the displayed formula of X and name it.
(2)
Name .................................................................................................................
(b) When isomer Y is heated under reflux with a mixture of potassium
dichromate(VI) and sulfuric acid, it forms 2-methylpropanoic acid.
Deduce the structural formula of the alcohol Y.
(1)
Q2.
21 Halogenoalkanes are important intermediates in organic chemistry. The
scheme below summarises some important reactions of a halogenoalkane.
(a) Identify the reagents and any specific conditions required for the reactions
in the diagram. (You may assume that a suitable temperature is maintained in
each reaction.)
(4)
A ........................................................................................................................
B ........................................................................................................................
C ........................................................................................................................
D ........................................................................................................................
(b) (i) Classify the type of reaction in each of A and D.
(2)
A ........................................................................................................................
D ........................................................................................................................
Q3.
This question is about two halogenoalkanes, X and Y, which have the
structures shown below.
(ii) Name Y.
(1)
............................................................................................................................
(iii) Write an equation for the reaction of X with an alcoholic solution of
ammonia, and name the organic product.
(2)
Name of product
............................................................................................................................
(iv) When Y is heated with an alcoholic solution of potassium hydroxide, the
alkene C4H8 is formed. What type of reaction occurs to produce the alkene?
(1)
............................................................................................................................
(b) Separate ethanolic solutions of X and Y were warmed with water
containing dissolved silver nitrate. Describe what would be seen in each case,
ignoring any differences in the rates of reaction.
(2)
Observation with X
............................................................................................................................
Observation with Y
............................................................................................................................
Q4.
(a) The products of the reaction when 2-chlorobutane is heated with sodium
hydroxide depend on the conditions.
(i) What condition, other than a suitable temperature and sodium hydroxide
concentration, would produce a mixture of but-1-ene and but-2-ene?
(1)
............................................................................................................................
(ii) What type of reaction occurs in (a)(i)?
(1)
............................................................................................................................
(iii) What condition, other than a suitable temperature and sodium hydroxide
concentration, would produce butan-2-ol in the reaction of 2-chlorobutane with
sodium hydroxide?
(1)
............................................................................................................................
(iv) Suggest the mechanism for the reaction of 2-chlorobutane with hydroxide
ions to form butan-2-ol. Use curly arrows to show the movement of electron
pairs.
(b) Phosphorus(V) chloride, PCl5, can be used to test for the –OH group.
Describe what would be seen when phosphorus(V) chloride is added to
butan‑2‑ol. Give the equation for the reaction. State symbols are not
required.
(2)
Observation ........................................................................................................
Equation
(ii) Give the structural formula of the organic product which forms when
butan‑2‑ol is oxidized.
(1)
Q5.
This is a question about halogenoalkanes.
(a) Halogenoalkanes can react with hydroxide ions in different ways
depending on the conditions used. Using 1-chloro-1-fluoroethane, CH3CHClF,
as an example of a halogenoalkane, the following reaction could occur in
aqueous solution.
CH3CHClF + OH−
→ CH3CHOHF + Cl–
(i) Suggest why it is unlikely that the fluorine atom in CH3CHClF would be
substituted by the hydroxide ion.
(1)
............................................................................................................................
............................................................................................................................
*(ii) A student attempted to draw the reaction mechanism for the reaction in
(a)(i), but made a total of three errors.
(c) (i) Chloroethane will react with alcoholic ammonia initially to produce
ethylamine. Complete the equation for this reaction.
(1)
...................... + NH3
→ ....................... + ..............................
(ii) Name the type and mechanism of the reaction occurring in (c)(i).
(2)
............................................................................................................................
............................................................................................................................
(iii) What feature of the ammonia molecule enables the reaction in (c)(i) to
take place?
(1)
............................................................................................................................
(iv) If aqueous ammonia was used in (c)(i), instead of alcoholic ammonia,
suggest the identity of the organic product that would be formed.
(1)
............................................................................................................................
Q6.
Halogenoalkanes react slowly with water to form alcohols. The equation for
the reaction is
RX + H2O
→ ROH + H+ + X–
(a) The rate of this reaction for different halogenoalkanes was investigated
using the apparatus below.
(iii) Name the precipitate formed in the test tube containing 1-bromobutane
and write an ionic equation for the formation of this precipitate. State symbols
are not required.
(2)
Precipitate ..........................................................................................................
Ionic equation
(iv) Predict the order (fastest first) in which the halogenoalkanes form
precipitates.
Explain your answer.
(2)
Order ..................................................................................................................
............................................................................................................................
Explanation ........................................................................................................
............................................................................................................................
............................................................................................................................
(b) Alcohols are usually prepared from halogenoalkanes using aqueous alkali,
rather than water, as the reaction is faster.
(i) Name the mechanism and type of reaction occurring when 1-bromobutane
reacts with aqueous alkali.
(2)
............................................................................................................................
(ii) Explain why the formation of alcohols is faster with aqueous alkali than
with water.
(1)
............................................................................................................................
............................................................................................................................
(iii) Give the mechanism for the reaction of 1-bromobutane with aqueous
alkali.
Show the lone pair involved in the mechanism and any relevant dipoles and
curly arrows.
(3)
(iv) One student suggested that the final reaction mixture could be tested for
the presence of an alcohol using phosphorus(V) chloride while another
suggested using potassium dichromate(VI) with sulfuric acid.
Describe the result of a positive test for alcohols using each of these
reagents.
Explain which test is better for the final reaction mixture.
(3)
Observation with PCl5 ........................................................................................
Observation with acidified K2Cr2O7 ....................................................................
Explanation ........................................................................................................
............................................................................................................................
............................................................................................................................
(c) 1-bromobutane is classified as a primary halogenoalkane and is one of
the four structural isomers with a molecular formula C4H9Br.
Give the skeletal formula of the three isomers, other than 1-bromobutane,
classifying the halogenoalkane in each case.
(3)
Q7.
(a) The rates of hydrolysis of three bromoalkanes are compared.
2 cm3 of ethanol is added to three test tubes, A, B and C.
Three drops of bromoalkane are added to each of these three test tubes.
1-bromobutane is added to test tube A.
2-bromobutane is added to test tube B.
2-bromo-2-methylpropane is added to test tube C.
2 cm3 of hot aqueous silver nitrate solution is added to each test tube.
(i) Explain why ethanol is added to each test tube.
(1)
............................................................................................................................
............................................................................................................................
(ii) Complete the general equation for the hydrolysis of these bromoalkanes.
State symbols are not required.
(1)
C4H9Br + H2O
→
(iii) Eventually a precipitate is formed in each test tube. Give the colour of the
precipitate formed and write the ionic equation, with state symbols, for its
formation.
(2)
Colour ................................................................................................................
Ionic Equation
(iv) Identify the reagent you could add to dissolve the precipitate.
(1)
............................................................................................................................
(v) Give the order in which the precipitates form in the test tubes A, B and C,
giving the fastest first.
(1)
............................................................................................................................
*(vi) State how the rates of hydrolysis depend on the structure of the
bromoalkane.
Suggest a reason for this difference. You are not required to give detailed
mechanisms for the reactions.
(2)
............................................................................................................................
............................................................................................................................
............................................................................................................................
............................................................................................................................
............................................................................................................................
(b) (i) When 1-bromobutane reacts with an alcoholic solution of sodium
hydroxide, a different reaction occurs.
Draw a fully labelled diagram to show the apparatus needed for carrying out
this reaction in the laboratory and collecting the gaseous organic product.
(2)
(ii) Name the organic product for this reaction and draw its skeletal formula.
(2)
Name .................................................................................................................
Skeletal formula
Q8.
This is a question about alcohols and compounds made from them.
(a) (i) Complete the table about some of the structural isomers with the
molecular formula C5H12O.
(3)
(ii) Identify, by name or formula, the alcohol which is the branched structural
isomer with molecular formula C5H12O that is not in the table.
(1)
(iii) Draw, and fully label, the apparatus that would be used to carry out the
complete oxidation of ethanol to ethanoic acid. Include any material that
would be used to ensure that boiling is controlled and not violent.
(3)
(iii) Calculate the mass of ethanoic acid in 500 cm3 of the diluted solution.
(2)
(ii) Write the equation for the incomplete combustion of hexan-1-ol which
produces only carbon and water. State symbols are not required.
(1)