10 organic chemistry - st leonard's college · draw the structures of the organic products...
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10 ORGANIC CHEMISTRY 1CHEMISTRY FOR THE IB DIPLOMA © CAMBRIDGE UNIVERSITY PRESS 2011
10 Organic chemistry
Revision checklistI am able to:
explain, using an example, what is meant by the term ‘homologous series’
sketch a graph of boiling point against number of carbons for the straight-chain alkane homologous series and explain the trend that is exhibited
draw structural formulas for the straight-chain alkanes up to C6
work out the molecular formula and empirical formula of the alkane with 12 carbon atoms
explain what is meant by the term structural isomers
draw structural formulas and name all isomers with the molecular formula C6H14
draw structural formulas and name all alkenes with the molecular formula C6H12
write the molecular formula and identify the functional groups present in each of the following:
explain why alkanes are unreactive
write balanced equations for the complete combustion of propane and butane
write a balanced equation for the incomplete combustion of propane, producing CO
write a balanced equation for the incomplete combustion of propane, producing soot
write an equation for the reaction of methane with chlorine and state the conditions required for the reaction to occur
write an equation for the reaction of ethane with bromine
write out the mechanism for the reaction between methane and chlorine
explain what is meant by the terms homolytic � ssion and free radical
state the names of the two organic products of the monochlorination of propane
draw the structure of but-1-ene
write an equation for the reaction of but-2-ene with hydrogen
write an equation for the reaction of but-2-ene with bromine
explain how alkanes may be distinguished from alkenes in the laboratory
write an equation using structural formulas for the reaction of but-2-ene with hydrogen chloride
write an equation for the reaction of ethene with water
write an equation using structural formulas to show the formation of a polymer from propene
state the type of polymerisation reaction involved in the formation of the polymer above
C H
H
O
H
OO
CC H
NH2
H
C
HHHO
H
CC
H
C
HHO
CC H
OH
H
C
HHO
H
C
H
C
H
C
HH
C
2 CHEMISTRY FOR THE IB DIPLOMA © CAMBRIDGE UNIVERSITY PRESS 201110 ORGANIC CHEMISTRY
draw the repeat unit and monomer for the polymer shown:
explain the economic importance of the hydrogenation of vegetable oils, hydration of ethene and polymerisation of alkenes
write an equation for the complete combustion of ethanol
draw and name all the isomers of C4H10O that are alcohols
classify each of the alcohols above as primary, secondary or tertiary
state the reagent and conditions required for the oxidation of alcohols
draw out and name the products of complete and partial oxidation (if any) of the alcohols drawn above
write balanced equations for the complete and partial oxidation of ethanol
explain the conditions that must be used to prepare an aldehyde from oxidation of a primary alcohol
write an equation for the reaction of bromoethane with aqueous sodium hydroxide
draw the structural formulas and name all the isomers of C4H9Cl
state whether each of the halogenoalkanes above is primary, secondary or tertiary
explain whether each of the halogenoalkanes above will react with aqueous sodium hydroxide via an SN1 or SN2 mechanism
state the meaning of all the terms in ‘SN1’ and ‘SN2’
draw out SN1 and SN2 mechanisms for suitable halogenoalkanes reacting with aqueous sodium hydroxide
complete the following table:
Homologous series Polarity Intermolecular forces Boiling point Solubility in water
alkane non-polar van der Waals’ low insoluble
alkene
alcohol
aldehydes/ketones
carboxylic acid
halogenoalkane
C
CH2
CH3
CH3
C
H
H
C
CH2
CH3
CH3
C
H
H
C
CH2
CH3
CH3
C
H
H
C
CH2
CH3
CH3
C
H
H
C
CH2
CH3
CH3
C
H
H
C
CH2
CH3
CH3
C
H
H
C
CH2
CH3
CH3
C
H
H
10 ORGANIC CHEMISTRY 3CHEMISTRY FOR THE IB DIPLOMA © CAMBRIDGE UNIVERSITY PRESS 2011
� ll in the reagents and conditions in the reaction scheme below:
HL
design a reaction pathway for the conversion of but-2-ene to butanone
name the following compounds:
H C
HH
HH
C H H C
H Br
H H
C H
H C H
H
BrBr
H H
C
H C Br
BrBr
H
C
C
H nH
HH
C
H C
H
H O
H
C H
H
H C
H O
OH
C
H
C CH H
H H
H C
H
H
O
H
C
CH3NH2
C
H
H
H C
H
H
C
O
H
H
C
H
H
C
H
H
C
H
H
H O
O
C
H
H
HN
N
H
C
H
H
C
H
H
H HC
H
H
C
H
C
H
H
H C NC
H
H
CH3
C C
H
H
state whether SN1 or SN2 reactions are generally faster
explain whether 1-chlorobutane or 1-iodobutane will react more quickly with aqueous sodium hydroxide solution
explain whether water or the hydroxide ion will react more rapidly with 1-bromobutane
state and explain how and why the rate of SN2 reactions depends on whether the halogenoalkane is primary, secondary or tertiary
state and explain how and why the rate of SN1 reactions depends on whether the halogenoalkane is primary, secondary or tertiary
write an equation for the reaction of bromoethane with ammonia
4 CHEMISTRY FOR THE IB DIPLOMA © CAMBRIDGE UNIVERSITY PRESS 201110 ORGANIC CHEMISTRY
draw the mechanism for the reaction of bromoethane with ammonia
write an equation for the reaction of bromoethane with potassium cyanide
draw the mechanism for the reaction of bromoethane with the cyanide ion
write an equation for the reaction that occurs when propanenitrile is heated with hydrogen
state the catalyst for the reaction above
state under which conditions 1-bromobutane will undergo an elimination reaction
write an equation for and give the mechanism for the elimination reaction above
draw the structures of the organic products formed when 2-bromobutane undergoes an elimination reaction
write an equation for the reaction of ethanol with ethanoic acid and state the essential conditions for the reaction
draw the structural formula of and name the ester formed when propanoic acid reacts with methanol
write an equation for the reaction of ethanamine (ethylamine) with propanoic acid
state the structural feature that must be present in monomers for them to be able to form condensation polymers
write an equation using structural formulas to show the formation of a polymer from ethane-1,2-diol and benzene-1,4-dicarboxylic acid
write an equation using structural formulas to show the formation of a polymer from 1,6-diaminohexane and hexanedioic acid
identify the monomers and the repeat unit for the polymer shown:
give three examples of the economic importance of condensation reactions
� ll in reagents and conditions in the following diagram:
H
C
C6H5
H
O O
C C
H
H
N
H
C
CH3
H
CH3
C
H
H
C
H
H
N
C
H
C
C6H5
H
O O
C C
H
H
N
H
C
H
C
H
H
C
H
H
N
C
H C
HH
BrH
C H
H C
H
H O
H
C H
H
C
H
H H
H
C H
H C
H O
OH
C
H
C CH H
H H
H C
H O
O
C
H
H H
H
C C NH C
H
H H
H
C C
H
H
N
H
HH
C
H
H
H
C H
H
H
N
H C
H
H
H
C H
H
C2H5
N
H
H
C
C
H
H
H
N C
H
H
H
H C
H O
H
C
C
H
H
H
N C
H
H
C
H
H
H
H C
H O
H
C
HL
10 ORGANIC CHEMISTRY 5CHEMISTRY FOR THE IB DIPLOMA © CAMBRIDGE UNIVERSITY PRESS 2011
design a reaction pathway for the conversion of 1-chloropropane to butylamine (butan-1-amine)
design a reaction pathway for the conversion of bromoethane to N-ethylpropanamide
explain what is meant by the term stereoisomerism
explain what is meant by the term geometrical isomerism
explain which of the following will exhibit geometrical isomerism:but-2-ene but-1-ene 3-methylpent-2-ene
draw out the structures of cis- and trans-1,2-dichloroethene, and explain which one is polar and which has the higher boiling point
draw out the structures of cis- and trans-but-2-ene-1,4-dioic acid, and explain which has the higher boiling point
describe a chemical reaction in which cis- and trans-but-2-ene-1,4-dioic acid behave di� erently
draw the structures of the geometrical isomers of 1,2-dimethylcyclobutane and explain why they exist
explain what is meant by the term ‘optical isomerism’
draw clear three-dimensional diagrams showing the optical isomers of butan-2-ol
state which of the following will exhibit optical isomerism:1-bromobutane 2-bromobutane CH3CH2CH(OH)COOH
explain what is meant by the terms enantiomer, chiral centre and asymmetric carbon atom
explain what is meant by the term plane-polarised light
explain how di� erent optical isomers interact with plane-polarised light
explain what a racemic mixture is
describe the similarities and di� erences in the physical and chemical properties of enantiomers
explain how a polarimeter may be used to distinguish between optical isomers
explain whether cis- or trans-1,2-dichlorocyclopropane exhibits optical isomerism
HL