10 Organic chemistry - St Leonard's College · draw the structures of the organic products formed when 2-bromobutane undergoes an elimination reaction write an equation for the reaction

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


� 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


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

10 Organic chemistry - St Leonard's College · draw the structures of the organic products formed when 2-bromobutane undergoes an elimination reaction write an equation for the reaction

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