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Unit 10b (Topic 10 and 20) Organic Chemistry
Nightly Homework
Lesson 0 – Pre-Introduction to Organic Chemistry
 Catenation
 Nucleophile
 Saturated
 Aliphatics
 Unsaturated
 Arenes
 Electrophile
Lessons 1 to 3 Intro To Orgo
 IUPAC
 Homologous series
 Structural isomer
 Skeletal formula




Homolytic
fission
Heterolytic
fission
Alkane, alkene, alkyne, alcohol,
ether
Aldehyde, ketone, carboxylic
acid
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Unit 10b (Topic 10 and 20) Organic Chemistry
Nightly Homework


Halogenoalkane, amine, ester,
nitrile, arene.
Hydroxyl, carboxyl


Cyclic and non-cyclic
Primary, secondary, tertiary
1. State the condensed structural formulas, together with their IUPAC names, for all
the structural isomers of C6H14.
2. Models showing the structural formulas of two compounds A and B, both with a
similar molar mass (74 and 72 g mol-1 respectively), are shown below:
(a) Identify the functional groups contained in compounds A and B.
(b) State the IUPAC names for compounds A and B.
(c) Deduce which of the two compounds, A or B, will have the higher boiling point
and which will be more soluble in water. Explain your deduction.
3. (a) State the IUPAC names of the following three alcohols:
(b) Classify these three alcohols in terms of primary, secondary or tertiary.
4. Identify the functional groups present in:
(a) Tyrosine and (b) Aspirin
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Unit 10b (Topic 10 and 20) Organic Chemistry
Nightly Homework
Lessons 4 and 5 Stereoisomerism
 conformational isomer
 configurational isomer
 E/Z
 CIP (Cahn–Ingold–Prelog)
priority
 chiral





enantiomer
diastereomer
racemic mixture
racemate
polarimeter
1. Deduce how many different four-membered ring isomers exist for
dichlorocyclobutane and name each isomer.
2. Explain why 1,2-dichloroethane cannot exhibit cis/trans isomerism whereas 1,2dichloroethene can. Explain whether or not 1,2-dichloroethane can show
conformational isomerism.
3. Explain why cis-butenedioic acid reacts to form a cyclic compound with the loss of
water when heated whereas trans-butenedioic acid does not.
4. 2-amino acids have the general formula H2NCH(R)COOH. Explain why glycine,
H2NCH2COOH, the simplest 2-amino acid, does not exist in two enantiomeric forms
whereas all the other 2-amino acids do.
5. Three of the first four compounds shown in Section 37 of the IB Chemistry data
booklet are the ‘over the counter’ pain killers, aspirin, paracetamol (acetaminophen)
and ibuprofen. Identify which, if any, can show optical isomerism. The fourth is
penicillin – can this also be optically active?
6. The straight chain structural formula of glucose is given in Section 34 of the
IBChemistry data booklet. Explain why glucose can have diastereomers.
7. Name the following compounds, A and B, using E/Z nomenclature.
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Unit 10b (Topic 10 and 20) Organic Chemistry
Nightly Homework
Lesson 6 Alkanes, Alkenes, and Addition Polymerization
 free radical
 addition
reaction
 initiation step
 hydrogenation
 propagation
step
 hydration
 termination
 halogenation
step
 symmetrical
alkene




addition
polymerization
poly(ethene)
poly(chloroethe
ne)
poly(propene)
1. State the balanced equations for the complete combustion (under standard
conditions) of 2-methylbutane, C5H12 (boiling point: 28 oC), 3-methylpentane,
C6H14, and octane, C8H18.
2. If the ratio of air to gasoline (petrol) entering a car engine is reduced then the
amount of air pollution caused by oxides of nitrogen emitted in the exhaust gas is
lowered. However, the concentration of two other air pollutants is increased.
Identify these two pollutants and explain how they arise.
3. The first step in the reaction between methane and chlorine in the presence of
ultraviolet light is the homolytic fission of the chlorine to chlorine single bond, ClCl(g), in gaseous chlorine.
(a) Explain the meaning of the term homolytic fission.
(b) Explain why homolytic fission occurs with the Cl-Cl bond in chlorine and
not the C-H bond in methane.
(c) State the name of the product formed when the Cl-Cl bond is broken
homolytically and state its electron configuration.
(d) Explain why only a few homolytic fission reactions involving chlorine
need to be successful in order to bring about the complete reaction between
chlorine and methane to form chloromethane and hydrogen chloride.
4. The reaction between bromine and ethane occurs in the presence of ultraviolet
light.
(a) Explain why ultraviolet light is necessary for the reaction to proceed.
(b) Describe, using equations, the stepwise mechanism of the reaction
between one mol of bromine and one mol of ethane to form one mol of
bromoethane and one mol of hydrogen bromide.
(c) Describe how you could make pure 1,2-dibromoethane from bromine and
ethane.
1. State the equation and name the organic product when propene reacts with:
(a) hydrogen using a nickel catalyst at 180oC.
(b) chlorine gas in the absence of water.
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Unit 10b (Topic 10 and 20) Organic Chemistry
Nightly Homework
2. Describe how you could distinguish practically between hexane and hex-3-ene by
using a simple chemical reaction. Describe what you would observe in each case and
state any relevant equations and name any products formed.
3. Ethanol is increasingly being produced commercially by the fermentation of crops
in order to use as a biofuel in place of/in addition to gasoline (petrol). This is
ecologically friendly in terms of greenhouse gas emissions but it is using up vast
areas of land which could be used for food production. Ethanol can also be made
industrially by the hydration of ethene. State the equation for the hydration of
ethene.
4. (a) State the equation and name the organic product when but-2-ene reacts with
hydrogen iodide.
(b) Unlike the reaction with but-2-ene, the reaction of but-1-ene with hydrogen
iodide is not on the IB Core. This is because in theory it can give two different
organic products although in practice only one of them is formed. Deduce the
identity of the two possible products.
5. (a) Draw the structure of the repeating unit of poly(chlorethene).
(b) Deduce the structure of the repeating unit of poly(tetrafluoroethene).
(c) Poly(tetrafluoroethene) is also known as ‘Teflon’ or ‘non-stick’ and it is used to
make artificial joints for humans as well as coat frying pans. Suggest a reason why it
is so unreactive.
Lesson 7 Alcohols
 primary
 secondary
 tertiary



reflux
distillation
esterification
1. State the equations for the complete combustion of:
(a) ethanol
(b) propan-2-ol
2. Propan-2-ol and propan-1-ol can both be oxidized by a warm acidified solution of
potassium dichromate(VI).
(a) Describe what would be observed in both cases.
(b) State the IUPAC name of the product from the oxidation of propan-2-ol
and state the simplified equation (use [O] to represent the oxygen from the
acidified potassium dichromate(VI) solution).
(c) The half-equation for the reduction of the acidified dichromate(VI) ion is:
Cr2O72–(aq) + 14H+(aq) + 6e– → 2Cr3+(aq) + 7H2O(l)
Deduce the full equation for the oxidation of propan-2-ol using acidified
Cr2O72– ions.
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Unit 10b (Topic 10 and 20) Organic Chemistry
Nightly Homework
(d) State the IUPAC name of the two organic products that can be formed
when propan-1-ol is oxidized by warm acidified potassium dichromate(VI)
solution.
(e) Explain why propan-1-ol can form two different organic products
whereas propan-2-ol only forms one organic product when oxidized by
acidified potassium dichromate(VI) solution.
(f) Describe how you could separate the two organic products formed from
the oxidation of propan-1-ol.
Lesson 8 and 9 Nucleophilic Substitution
 'curly' arrow
 heterolytic fission
 SN1 (unimolecular nucleophilic
substitution)
 SN2 (bimolecular nucleophilic
substitution)




carbocation
transition state
protic solvent
aprotic solvent
1. Explain the following statements:
(a) hydroxide ions are better nucleophiles than water molecules.
(b) the hydrolysis of iodoethane is faster than the hydrolysis of bromoethane.
(c) the hydrolysis of 2-bromo-2-methylpropane is faster than the hydrolysis
of 1-bromobutane.
(d) fluoroethane does not react with dilute sodium hydroxide solution to
form ethanol.
2. Explain the mechanism for the reaction of ammonia with bromoethane. (Use curly
arrows to show the movement of pairs of electrons.)
3. (a) Explain why the substitution of primary halogenoalkanes by hydroxide ions
could also be classed as a Lewis acid-base reaction.
(b) Explain whether the reaction of tertiary halogenoalkanes with hydroxide ions
could also be classed as a Lewis acid-base reaction.
4. Suggest how tetramethylammonium bromide, (CH3)4N+Br–, could be made from
bromomethane.
Lesson 10 Electrophilic Addition
 Markovnikov
 carbocation
 electrophile
 electrophilic addition



induced dipole
asymmetric
interhalogen
1. Bromine is a non-polar molecule.
(a) Explain how it is able to act as an electrophile when it adds to ethene.
Nomen: ____________________________________________________ Dies:____________________________
Unit 10b (Topic 10 and 20) Organic Chemistry
Nightly Homework
(b) Name the product when bromine is added to ethene in the absence of
water.
(c) Explain why the major product obtained is 2-bromethanol if bromine
water is added to ethene.
2. Describe the mechanism for the addition of hydrogen bromide to prop-1-ene.
Your answer should include the use of curly arrows to show the movement of
electron pairs and give the structure and IUPAC name for the major product formed.
3. Deduce the structure and IUPAC name of the major product formed when iodine
chloride, I-Cl, is added to but-1-ene.
4. Draw the structure of the intermediate carbocation formed when 2-methylbut-2ene reacts with hydrogen chloride and state whether the carbocation is primary,
secondary or tertiary.
Lesson 11 Electrophilic Substitution
 arene
 nitration


nitronium ion
electrophilic substitution
1. Describe and explain the structure of benzene by considering the hybridization
that occurs on each carbon atom.
2. Benzene reacts with a mixture of concentrated nitric and sulfuric acid at a
temperature not exceeding 50 oC.
(a) State the equation for the reaction that occurs.
(b) Explain the role of the concentrated sulfuric acid.
(c) Identify the electrophile in this reaction.
(d) Explain why substitution rather than addition occurs.
(e) Show the mechanism for this reaction using curly arrows.
(f) Suggest a reason why the temperature is not raised above 50 oC.
3. Benzene can also undergo an electrophilic substitution reaction with chlorine in
the presence of aluminum chloride, AlCl3, to form chlorobenzene.
(a) Deduce the equation for this reaction.
(b) Based on your knowledge of electrophiles suggest the identity of the
electrophile in this reaction and deduce the role of aluminum chloride in its
formation.
Lesson 11 – Reduction
 sodium borohydride, NaBH4
 lithium aluminium hydride, LiAlH4
 phenylamine, C6H5NH2
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Unit 10b (Topic 10 and 20) Organic Chemistry
Nightly Homework
1. Two different organic products can be obtained when 2-methylbutanoic acid is
reduced using lithium aluminum hydride, LiAlH4.
Identify the two organic products by giving their systematic (IUPAC) name and
write equations for the reactions.
2. There are four different alcohols that are structural isomers with the molecular
formula C4H10O.
(a) Identify the four different structural alcohols by giving their systematic
(IUPAC) name.
(b)Three of the four different alcohols can be prepared by reducing an
aldehyde or a ketone using sodium borohydride, NaBH4. Identify which three
together with the aldehyde or ketone that can be used to prepare it.
(c) Explain why the fourth alcohol cannot be prepared by reducing an
aldehyde or ketone.
3. Phenylamine can be prepared by firstly refluxing nitrobenzene with a mixture of
tin metal and concentrated hydrochloric acid then reacting the organic product
formed from this first step with sodium hydroxide solution.
(a) Identify the role played by the tin metal in this reaction.
(b) State the name of the intermediate organic compound formed in this
reaction and state the half-equation for its formation.
(c) State the equation for the reaction of this intermediate organic product
with sodium hydroxide to form phenylamine.
Lesson 12 – Synthesis
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Unit 10b (Topic 10 and 20) Organic Chemistry
Nightly Homework
1. Starting with 2-methylpropane deduce a synthetic pathway to make 2methylpropanoic acid.
CH3CH(CH3)CH3 → CH3CH(CH3)COOH
For each step specify the reagents and any necessary conditions and write an
equation for each step.
2. Design a synthetic route to make butanone starting with but-1-ene.
CH3CH2CHCH2 → CH3CH2COCH3
Knowing that the first step involves the addition of hydrogen bromide to but-1-ene
state the name of the mechanism for the first two steps.
3. You are provided with ethanal and any inorganic reagents and laboratory
equipment you require but no other organic compounds. Design a method to
synthesise ethylethanoate from ethanal.
CH3CHO → CH3COOC2H5
For each step specify the reagents and any necessary conditions.
4. Show how phenylamine can be synthesised from benzene.
5. Propyl ethanoate is used as a solvent and has the characteristic smell of pears.
Design a synthetic route to make propyl ethanoate starting from 1-chloropropan
and chloroethane as the only organic compounds available.