A2 APPLIED ORGANIC CHEMISTRY II - … · A2 TOPIC 26 APPLIED ORGANIC CHEMISTRY II ... (styrene)....
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APPLIED ORGANIC CHEMISTRY II A2 TOPIC 26 FRIEDEL-CRAFTS AS A SYNTHESIS STARTING POINT POLYESTERS POLYAMIDES PERFUMES OILS AND FATS APPLICATIONS OF NITRATION AZO DYES PHARMACEUTICALS I PHARMACEUTICALS II ADDITION POLYMERS ISOMERISM IN PERFUMES & INSECT-REPELLENTS Questionsheet 1 Questionsheet 2 Questionsheet 3 Questionsheet 4 Questionsheet 5 Questionsheet 6 Questionsheet 7 Questionsheet 8 Questionsheet 9 Questionsheet 10 Questionsheet 11 QUESTIONSHEETS A2 Level CHEMISTRY 17 marks 15 marks 16 marks 17 marks 17 marks 19 marks 10 marks 14 marks 8 marks 18 marks 20 marks Curriculum Press – Licence Agreement: Paper copies of the A-Level Chemistry Questionsheets may be copied free of charge by teaching staff or students for use within their school, provided the Photocopy Masters have been purchased by their school. No part of these Questionsheets may be reproduced or transmitted, in any other form or by any other means, without the prior permission of the publisher. All rights are reserved. This license agreement is covered by the laws of England and Wales © Curriculum Press March 2008. Curriculum Press • Bank House • 105 King Street • Wellington • Shropshire • TF1 1NU ress urriculum C P www.curriculum-press.co.uk Authors Trevor Birt John Brockington Donald E Caddy Kevin Frobisher Andrew Jones Andy Shepherd Adrian Bond Stuart Barker Editors John Brockington Stuart Barker
Transcript of A2 APPLIED ORGANIC CHEMISTRY II - … · A2 TOPIC 26 APPLIED ORGANIC CHEMISTRY II ... (styrene)....
APPLIED ORGANIC CHEMISTRY IIA2 TOPIC 26
FRIEDEL-CRAFTS AS A SYNTHESIS STARTING POINT
POLYESTERS
POLYAMIDES
PERFUMES
OILS AND FATS
APPLICATIONS OF NITRATION
AZO DYES
PHARMACEUTICALS I
PHARMACEUTICALS II
ADDITION POLYMERS
ISOMERISM IN PERFUMES & INSECT-REPELLENTS
Questionsheet 1
Questionsheet 2
Questionsheet 3
Questionsheet 4
Questionsheet 5
Questionsheet 6
Questionsheet 7
Questionsheet 8
Questionsheet 9
Questionsheet 10
Questionsheet 11
QUESTIONSHEETS A2 LevelCHEMISTRY
17 marks
15 marks
16 marks
17 marks
17 marks
19 marks
10 marks
14 marks
8 marks
18 marks
20 marks
Curriculum Press – Licence Agreement:Paper copies of the A-Level Chemistry Questionsheetsmay be copied free of charge by teaching staff or studentsfor use within their school, provided the PhotocopyMasters have been purchased by their school. No part ofthese Questionsheets may be reproduced or transmitted,in any other form or by any other means, without theprior permission of the publisher. All rights are reserved.This license agreement is covered by the laws of Englandand Wales © Curriculum Press March 2008.
Curriculum Press • Bank House • 105 King Street • Wellington • Shropshire • TF1 1NU
ressurriculumCPwww.curriculum-press.co.uk
AuthorsTrevor Birt John BrockingtonDonald E Caddy Kevin FrobisherAndrew Jones Andy ShepherdAdrian Bond Stuart Barker
EditorsJohn BrockingtonStuart Barker
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FRIEDEL-CRAFTS AS A STARTING POINTTOPIC 26 Questionsheet 1
Methylbenzene is an important starting material in the synthesis of many compounds.a) It can be prepared by the reaction of bromomethane and benzene.
(i) Identify a third substance necessary for this reaction.
....................................................................................................................................................................... [1](ii) What is the purpose of this third substance?
....................................................................................................................................................................... [1](iii) What type of reaction is involved?
....................................................................................................................................................................... [1]
b) The blue dye indigo can be manufactured by a process that has an intermediate stage producing 2-aminobenzoicacid :
CH3
COOH
NH2
ACH
3
NH2
B
KMnO4 /base
(i) Give the structure of A and B
A B
[2](ii) Give the reagents used in steps 1 and 2
step 1 ..................................................................................................................................................... [1]
step 2 ..................................................................................................................................................... [1]
(iii) The next stage in the process involves 2-aminobenzoic acid reacting with chloroethanoic acid(ClCH
2COOH) to form Q and hydrogen chloride.
Suggest a structure for the product Q
[1]
(iv) What type of reaction is involved in this stage?
...........................................................................................................................................................................
....................................................................................................................................................................... [2]
(Continued...)
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FRIEDEL-CRAFTS AS A STARTING POINTTOPIC 26 Questionsheet 1 Continued
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c) 2-methylphenol is an initial structure in the manufacture of pesticides and disinfectants. It can be synthesisedfrom 2-aminomethylbenzene (an intermediate in the synthesis of indigo) as follows:
CH3
NH2
X
CH3
OH
I II
(i) Give the reagents and conditions for stages I and II:
I Reagents ......................................................................................................................................... [1]
Conditions ...................................................................................................................................... [1]
II Reagents ......................................................................................................................................... [1]
Conditions ...................................................................................................................................... [1]
(ii) Give the structure of X
...................................................................................................................................................................... [1}
(iii) What is the general name for compounds like X?
....................................................................................................................................................................... [1]
(iv) X can be used to prepare important class of coloured compounds, what are they called?
....................................................................................................................................................................... [1]
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POLYESTERSTOPIC 30 Questionsheet 2
a) I CH3COOH and HOCH
2CH
2OH
II HOOCCH=CHCOOH and HOCH2CH
2CH
2OH
III COOH
One of the above pairs of compounds will react together to give a linear polyester. Identify the correct pair,write down the formula of the polymer so as to show the repeating unit in the chain, and state the type ofpolymerisation.
Correct pair .................................................................................................................................................. [1]
Formula of polymer ....................................................................................................................................... [2]
Type of polymerisation .................................................................................................................................. [1]
b) Given that esterification is a reversible reaction, suggest how, in the formation of a polyester, the equilibriumcould be disturbed so as to give almost complete conversion (rather than an equilibrium mixture).
...........................................................................................................................................................................
...........................................................................................................................................................................
....................................................................................................................................................................... [3]
Quality of language [1]
c) Contrast the behaviour of the polymer from a) with that of poly(phenylethene) (polystyrene) in its resistanceto attack by NaOH(aq). State the type of any reaction that occurs and identify the reaction products.
Polymer from a) .................................................................................................................................................
...........................................................................................................................................................................
Poly(phenylethene) ............................................................................................................................................
....................................................................................................................................................................... [4]
d) Although the polyester referred to in a) will dissolve in methylbenzene without reaction, there is neverthelessa further polymerisation when it is dissolved in phenylethene (styrene). Suggest a reason for this, and describewhat type of polymerisation is likely to occur.
Reason ........................................................................................................................................................... [1]
Type of polymersation .......................................................................................................................................
....................................................................................................................................................................... [2]
and CH3OH
COOH
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POLYAMIDESTOPIC 26 Questionsheet 3
a) Nylon manufactured in the UK is referred to as nylon 66. State what this means, and indicate what other sortsof nylon are possible.
Meaning ..........................................................................................................................................................
....................................................................................................................................................................... [2]
Other sorts ......................................................................................................................................................
....................................................................................................................................................................... [2]
b) Write a balanced chemical equation for the formation of nylon 66, showing clearly the repeating unit in thepolymer chain.
....................................................................................................................................................................... [3]
c) Polyamides and proteins have a common structural feature which is responsible for strong attraction betweentheir molecules.
(i) What is the name of this feature?
....................................................................................................................................................................... [1]
(ii) Draw its structure.
....................................................................................................................................................................... [1]
(iii) What type of attraction does it cause?
....................................................................................................................................................................... [1]
(iv) Why should the absence of this structural feature cause the molecules of a polyester, such as Terylene,to be less strongly attracted together?
...........................................................................................................................................................................
....................................................................................................................................................................... [2]
d) In the laboratory, a form of nylon can be made from hexanedioyl chloride and hexane-1,6-diamine.
(i) Why is this method of preparation (rather than the industrial method) used in the laboratory?
....................................................................................................................................................................... [1]
(ii) Calculate the minimum masses of hexanedioyl chloride, ClCO(CH2)
4COCl, and hexane-1,6-diamine,
H2N(CH
2)
6NH
2, which would be needed to prepare 100 g of ‘laboratory nylon’.
...........................................................................................................................................................................
...........................................................................................................................................................................
...........................................................................................................................................................................
....................................................................................................................................................................... [3]
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PERFUMES
TOPIC 26 Questionsheet 4
1-Phenylethanol has a strong odour of flowers, and 2-phenylethanol smells mildly of roses. Both are widely usedas synthetic fragrances.
a) A synthetic route is shown to prepare 2-phenylethanol from methylbenzene, starting with the free radicalchlorination of methylbenzene in the side chain.
State the reagents and conditions required for each of the stages 1-4.
Stage 1
Reagent .......................................................................................................................................................... [1]
Conditions ..................................................................................................................................................... [1]
Stage 2
Reagent .......................................................................................................................................................... [1]
Conditions ..................................................................................................................................................... [2]
Stage 3
Reagent .......................................................................................................................................................... [1]
Conditions ..................................................................................................................................................... [1]
Stage 4
Reagent .......................................................................................................................................................... [1]
Conditions ..................................................................................................................................................... [1]
CH3
Stage 1
CH2Cl
Stage 2
CH2CN
Stage 3
CH2COOH
Stage 4
CH2CH
2OH
Methylbenzene 2-Phenylethanol
(Continued...)
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TOPIC 26 Questionsheet 4 Continued
PERFUMES
b) Devise a three-stage synthesis for the laboratory preparation of 1-phenylethanol form 2-phenylethanol.Complete the scheme below by writing the formulae of Compounds A and B, and then give details of thereagents and reaction conditions required for each stage.
[2]
Stage 1
Reagent .......................................................................................................................................................... [1]
Conditions ..................................................................................................................................................... [1]
Stage 2
Reagent .......................................................................................................................................................... [1]
Conditions ..................................................................................................................................................... [1]
Stage 3
Reagent .......................................................................................................................................................... [1]
Conditions ..................................................................................................................................................... [1]
Stage 1
CH2CH
2OH
2-Phenylethanol
Stage 2 Stage 3
CH(OH)CH3
1-PhenylethanolCompound A Compound B
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OILS AND FATS
TOPIC 26 Questionsheet 5
a) Animal and vegetable oils and fats are described as triglycerides. Explain what is meant by a ‘triglyceride’.
...........................................................................................................................................................................
....................................................................................................................................................................... [2]
b) How are vegetable oils converted into margarine? State the reagent, the catalyst, and the way in which thecatalyst is removed from the product.
Reagent .......................................................................................................................................................... [1]
Catalyst .......................................................................................................................................................... [1]
Removal of catalyst ....................................................................................................................................... [1]
c) Soap is made by the saponification of low grade fats and oils.
(i) Saponification means literally ‘soap formation’. What type of chemical reaction is involved?
....................................................................................................................................................................... [1]
(ii) State the reagent and conditions needed for saponification. Support your answer by writing a chemicalequation. (Use ‘RCOOH’ to represent a carboxylic acid.)
Reagent & conditions ............................................................................................................................ [3]
Equation
[3]
(iii) State how soap is extracted from the solution after saponification, and briefly explain the underlying theory.
Method of extraction ............................................................................................................................. [1]
Theory .......................................................................................................................................................
...................................................................................................................................................................
............................................................................................................................................................... [3]
(iv) State one major product (or type of product) which is manufactured from glycerol in the chemical industry.
....................................................................................................................................................................... [1]
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APPLICATIONS OF NITRATION
TOPIC 26 Questionsheet 6
a) In the chemical industry, arenes (aromatic hydrocarbons) are nitrated for the manufacture of explosives.Polynitro compounds are more effective for this application than mononitro compounds.
(i) What are the usual reagents for nitrating arenes?
....................................................................................................................................................................... [2]
(ii) State two ways in which the formation of polynitroarenes can be favoured, rather than mononitrocompounds.
...........................................................................................................................................................................
....................................................................................................................................................................... [2]
(iii) It is easier to obtain 2,4,6-trinitromethylbenzene (trinitrotoluene, or TNT) than it is to obtain 1,3,5-trinitrobenzene. In methylbenzene, what does this suggest about the benzene ring and the effect of themethyl group?
...........................................................................................................................................................................
...........................................................................................................................................................................
....................................................................................................................................................................... [3]b) (i) On detonation, the nitrogen atoms in a nitro compound are principally converted into gaseous nitrogen.
Suggest why it is that polynitro compounds are more effective as high explosives than mononitrocompounds.
....................................................................................................................................................................... [2](ii) Use the equation below to calculate the total volume of gas produced at room temperature and pressure.
By detonating 100 g of TNT. (Assume that 1 mol of gas occupies 24.0 dm3 at room temperature andpressure.) 4C
6H
2(CH
3)(NO
2)
3(s) → 7CO
2(g) + 10H
2O(g) + 6N
2(g) + 21C(s)
...........................................................................................................................................................................
...........................................................................................................................................................................
....................................................................................................................................................................... [4]
(iii) To increase the effectiveness of TNT, potassium chlorate(VIII) ( KClO4 ) can be added. Suggest why
this is done and how this increases the explosive efficiency
....................................................................................................................................................................... [2]c) The nitration of arenes is also important for manufacturing products of a very different kind whose molecules
contain the group –N=N- .(i) What do we call this group?
....................................................................................................................................................................... [1](ii) What kind of products are they?
....................................................................................................................................................................... [1](ii) Fill in the missing words in the phrases describing the stages by which such products are made from
nitrated arenes. ........………….......to an amine
…………………...of the amine
Coupling with an amine or a ……………. [3]
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AZO DYESTOPIC 26 Questionsheet 7
(i) The starting materials for preparing Orange II are an aminosulfonic acid, A, and a phenolic compound,B. Write down the structural formulae of A and B. (The functional group in sulfonic acids is –SO
3H.)
A = B =
[2]
(ii) Write an equation for the diazotisation of A in dilute hydrochloric acid.
[2]
(iii) State the conditions for the coupling reaction.
....................................................................................................................................................................... [2]
(iv) Suggest a reason for introducing a sulfonic acid group (and hence the –SO3 Na grouping) into an azo
dye.
....................................................................................................................................................................... [1]
-
+
a) (i) Why would a compound appear coloured in normal light?
...........................................................................................................................................................................
....................................................................................................................................................................... [2] (ii) Draw the structure of the group found in all azo dyes that is responsible for their colour.
[1]
b) Some azo dyes are made by coupling reactions between diazonium salts and phenolic compounds. An exampleis ‘Orange II’, shown below.
OHN N SO
3
-
Na
+
Orange II
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PHARMACEUTICALS I
TOPIC 26 Questionsheet 8
14
a) Paracetamol, oil of wintergreen and aspirin are classified as analgesics.
(i) What is meant by an ‘analgesic’?
....................................................................................................................................................................... [1]
(ii) Which two of the three analgesics shown above are suitable for taking by mouth? Explain your answer.
Suitable for taking by mouth ................................................................................................................. [1]
Explanation ...............................................................................................................................................
............................................................................................................................................................... [2]
(iii) State how the analgesic which is not suitable for taking by mouth is applied and explain, in terms of itsmolecular structure, how it reaches its target.
Method of application ........................................................................................................................... [1]
Explanation ...............................................................................................................................................
...................................................................................................................................................................
............................................................................................................................................................... [3]
b) Both aspirin and oil of wintergreen are made from salicylic acid (2-hydroxybenzenecarboxylic acid).
(i) Name a reagent which is suitable for converting salicylic acid to aspirin.
....................................................................................................................................................................... [1](ii) Give a reagent and catalyst for converting salicylic acid to oil of wintergreen.
Reagent .................................................................................................................................................. [1]
Catalyst ................................................................................................................................................. [1]
c) Paracetamol is made from 4-aminophenol.
(i) Name a suitable reagent for the conversion.
....................................................................................................................................................................... [1]
(ii) Write an equation for the reaction.
[1]
(iii) What type of functional group has been introduced?
....................................................................................................................................................................... [1]
CO O
HO
CO
CH3
CO O
CH3
O HN
H C
O
CH3
O HParacetamol Oil of wintergreen Aspirin
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a) Study the structural formulae of the two pain relieving drugs, aspirin and ibuprofen.
TOPIC 30 Questionsheet 9
PHARMACEUTICALS II
CO O
HO
CO
CH3
C
O H
O
H C
CH3
(i) One of these drugs has a chiral centre. Mark this clearly on the molecule concerned. [1]
(ii) Draw structures to show the two enantiomers (stereoisomers) of this drug.
[2]
(iii) Explain why the other drug is not chiral.
...........................................................................................................................................................................
....................................................................................................................................................................... [2]
b) Many modern drugs have a chiral centre. Explain the importance of this.
...........................................................................................................................................................................
...........................................................................................................................................................................
....................................................................................................................................................................... [3]
CH2
CH(CH3)
2
Aspirin Ibuprofen
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ADDITION POLYMERSTOPIC 26 Questionsheet 10
a) Poly(methyl methacrylate) (‘PMMA’)is a clear plastic used for LCD and TV screens to make light spreadevenly. Methyl methacrylate has the structure:
(i) Give a diagram to show two repeat units of the polymer.
[2](ii) What type of chemical species is the reactive group in the polymerisation mechanism?
....................................................................................................................................................................... [1](iii) Suggest two properties of the polymer that make it useful for the stated purpose.
....................................................................................................................................................................... [2]
b) A co-polymer of methyl methacrylate and (2-hydroxyethyl) methacrylate is used for nerve guidance channelsafter spinal injuries. An important criterion for the nerve guidance channel is that its mechanical properties aresimilar to those of the spinal cord, where it will be implanted. This relies on it behaving as a hydrogel.
(i) What does the term co-polymer mean?
....................................................................................................................................................................... [1](ii) Draw a repeat unit of this polymer involving both monomers.
[2] (iii) Suggest and explain a reason for the improved flexibility of this co-polymer compared to poly(methyl
methacrylate).
....................................................................................................................................................................... [2]c) (i) Write an equation for the polymerisation of styrene (phenylethene).
[2](ii) Name a suitable catalyst for the polymerisation.
....................................................................................................................................................................... [1](iii) Why is polystyrene such a brittle plastic?
....................................................................................................................................................................... [1]d) Expanded polystyrene is made by heating granules of polystyrene until they soften and then gassing them.
(i) Suggest a suitable gas for the purpose.
....................................................................................................................................................................... [1](ii) Why would it not be sensible to use air for this purpose?
....................................................................................................................................................................... [1](iii) State two physical properties of expanded polystyrene that make it an ideal material to use for making
calorimeters.
1 .................................................................................................................................................................
2 ............................................................................................................................................................. [2]
CH3
C COOCH3
CH2
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A2 Level TOPIC 26 Questionsheet 11
a) Citral is found in plants such as lemon myrtle and lemongrass.
(CH3)
2C=CHCH
2CH
2C=CHCHO
CH3
A B
Both forms have a lemon odour and are used in perfumery.(i) What is the molecular formula of Citral?
....................................................................................................................................................................... [1]
(ii) Which double bond (A or B) determines that E/Z isomers can exist?
....................................................................................................................................................................... [1]
(iii) Complete this table:
Group in citral molecule Test to show presence of Observation for positive resultgroup in citral
−CH=CH−
−CHO
(iv) Explain why citral does not exhibit optical isomerism.
....................................................................................................................................................................... [1]
b) HBr reacts with citral. Optical isomers are formed but the product is optically inactive.
(i) State which double bond (A or B) gives rise to such isomers and give diagrams to show the two formsthat give this isomerism.
[3](ii) Explain why the product is optically inactive
...........................................................................................................................................................................
....................................................................................................................................................................... [2]
(iii) Use the mechanism for the addition of HBr to explain how this apparent inactivity arises
[4]
ISOMERISM IN PERFUMES & INSECT-REPELLENTS
(Continued...)
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A2 Level TOPIC 26 Questionsheet 11 Continued
ISOMERISM IN PERFUMES & INSECT-REPELLENTS
c) Citronellal is extracted from lemon-scented teatree oil and is used as a mosquito repellent and anti-fungalagent.
(CH3)
2C=CHCH
2CH
2CHCH
2CHO
CH3
(i) Would you expect citronellal to be optically active? Explain your answer.
...........................................................................................................................................................................
...........................................................................................................................................................................
....................................................................................................................................................................... [2]
(ii) Warming with acidified potassium dichromate(VI) forms a product that is comparatively ineffective forthe above uses. What does this suggest?
...........................................................................................................................................................................
...........................................................................................................................................................................
....................................................................................................................................................................... [2]
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