DP IB Chemistry: HL

Topic Questions

Syllabus Edition

First teaching 2014

Last exams 2024

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10.2 Functional Group Chemistry

11 mark

Which of these organic compounds would undergo free radical substitution?

 

1

          ethane

2

          fluoroethane

3

          ethene

4

          ethanal

  • 1 only

  • 1 and 2

  • 1, 2 and 3

  • All

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21 mark

Which of these compounds would act as a nucleophile?

  • C2H6

  • H+

  • OH-

  • Al

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31 mark

Which equation represents a correct propagation step in the free radical substitution reaction between ethane and chlorine?

  • C2H6 + Cl → C2H5Cl + H

  • C2H5 + Cl2  → C2H5Cl + Cl 

  • C2H6 + H → C2H5 + HCl

  • C2H5 + Cl → C2H5Cl 

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41 mark

Ethene reacts with steam in the presence of sulfuric acid.

C2H4  +  H2O →  CH3CH2OH

What type of reaction is this?

 

  • acid / base

  • addition

  • hydrolysis

  • substitution

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51 mark

A molecule of a polymer contained the sequence shown.10-2-e-q5-ib-chemistry-mcqs

Which monomer could produce this polymer by addition polymerisation?

  • CHCl =CHCl

  • CH2=CHCl

  • CH3CCl =CHCl

  • CH3CCl =CH2

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61 mark

The compound ‘leaf alcohol’ is partly responsible for the smell of new-mown grass.

CH3CH2CH=CHCH2CH2OH

leaf alcohol

What product will be formed when ‘leaf alcohol’ is oxidised using an excess of hot, acidified K2Cr2O7(aq)?

  • CH3CH2CH(OH)CH(OH)CH2CO2H

  • CH3CH2COCOCH2CO2H

  • CH3CH2CH=CHCH2CO2H

  • CH3CH2CO2H and HO2CCH2CO2H

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71 mark

Which of the alcohols shown below will decolourise acidified potassium manganate(VII)?

I.    

CH3CH2CH2CH2OH

II.  

  CH3CH(OH)CH2CH3

III.  

(CH3)3CCH2OH

  • I and II only  

  • I and III only  

  • II and III only 

  • I, II and III

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81 mark

Ultraviolet light initiates the following reaction.

alkane + chlorine → chloroalkane + hydrogen chloride

What happens to chlorine in this photochemical reaction?

  • heterolytic fission to give an electrophile

  • homolytic fission to give an electrophile

  • heterolytic fission to give a positive and negative ion

  • homolytic fission to give free radicals

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91 mark

Which reaction is an example of nucleophilic substitution?

  • C6H6 + Br2 → C6H5Br+ HBr

  • CH2=CH2 + HBr → CH3CH2Br

  • C3H7Br + H2O → C3H7OH + HBr

  • C2H6 + Br2 → C2H5Br + HBr

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101 mark

Bromomethane, CH3Br, is used as a fumigant to destroy insect pests in grain that is to be stored. It can be made by reacting methanol with hydrogen bromide.

CH3OH  +  HBr  →  CH3Br  + H2O

What type of reaction is this?

  • condensation

  • electrophilic substitution

  • free radical substitution

  • nucleophilic substitution

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111 mark

What reagents and conditions are needed to convert but-2-ene into butane?

  • Concentrated sulfuric acid, steam, 300oC

  • Hydrogen gas, Ni catalyst, 150oC

  • Acidified potassium dichromate, heating under reflux

  • Hydrogen bromide, room temperature

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121 mark

Which of the following products are possible from the incomplete combustion of alkanes?

I.  

   C

II.    CO

III.    

H2

  • I and II only

  • I and III only

  • II and III only

  • I, II and III

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131 mark

What can be produced when an aqueous solution of butan-2-ol is oxidised under suitable conditions?

 

1

butanone

2

butanoic acid

3

butanal

  • 1, 2 and 3

  • 1 and 2 only

  • 2 and 3 only

  • 1 only

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141 mark

The ester in the diagram below has an odour of banana.

10-2-e-q14-ib-chemistry-mcqs

Which pair of reactants can be used to produce this ester under suitable conditions?

10-2-e-q14-options-ib-chemistry-mcqs

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11 mark

Limonene is an oil formed in the peel of citrus fruits.10-2-h-q1-ib-chemistry-mcqs

Which product is formed when an excess of bromine, Br2(l), reacts with limonene at room temperature in the dark?10-2-h-q1-i-ib-chemistry-mcqs

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21 mark

Samples of 10 cm3 of each of the first four members of the alkane series are separately mixed with 70 cm3 of oxygen. Each is then burned and the total volume, V, of residual gas measured again at room temperature and pressure.

Which graph represents the results that would be obtained?10-2-h-q2-ib-chemistry-mcqs

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31 mark

A periodic table is needed for this question

Which compound has an Mr of 84.18 and will react with HBr to give a product with an Mr of 165.09?10-2-h-q3-ib-chemistry-mcqs

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41 mark

An organic compound Y with molecular formula C5H12O, is oxidised to compound Z with molecular formula C5H10O2.

What could be the structural formula of Y?

1

          CH3(CH2)4OH

2

          CH3CH2CH(CH2OH)CH3

3

          CH3C(CH3)2CH2OH

  • 1, 2 and 3

  • 1 and 3 only

  • 2 and 3 only

  • 3 only

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51 mark

A periodic table is needed to answer this question

A number of alcohols with the formula C4H10O are separately oxidised. Using 7.41 g of the alcohols a 50% yield of organic product is achieved.

What mass of product could be obtained?

1

          4.41 g of butanoic acid

2

          4.41 g of 2-methylpropanoic acid

3

          3.61 g of butanone

  • 1, 2 and 3

  • 1 and 2 only

  • 2 and 3 only

  • 1 only

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61 mark

Which compound is produced in the reaction between pent-2-ene and steam?

  • (CH3)2CHCH2CH2OH

  • CH3CH(OH)CH2CH2CH2CH3

  • CH3CH2CH2CH2CH2OH

  • CH3CH2CH2CH(OH)CH3

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71 mark

When compound T reacts with its own oxidation product, a sweet-smelling liquid is produced.

What is the identity of compound T?

  • butanal

  • butanone

  • butan-1-ol

  • butanoic acid

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81 mark

In the presence of an H+ catalyst, compound X reacts with ethanoic acid to produce the compound below.

10-2-m-q8-ib-chemistry-mcqs

What is the molecular formula of compound X?

  • C4H8

  • C4H8O2

  • C2H6O2

  • C2H6O3

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91 mark

Compound K, C5H12O, is oxidised by acidified sodium dichromate(VI) to compound L.

Compound L reacts with butan-2-ol in the presence of a little concentrated sulfuric acid to give liquid M.

What could be the formula of liquid M?

  • (CH3)2CHCH2CO2C(CH3)3

  • CH3(CH2)3CO2(CH2)3CH3

  • CH3(CH2)3CO2CH(CH3)CH2CH3

  • CH3(CH2)2CO2CH2CH2(CH3)2

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101 mark

Shown below is a reaction sequence starting with 1-chlorobutane.

    I                          II                                  III

     C4H9Cl      → C4H9OH        →        C3H7COOH      →     C3H7COOC3H7

What is the correct classification of the types of reactions shown?

 

I

II

III

A

substitution

oxidation

substitution

B

addition

substitution

condensation

C

oxidation

substitution

condensation

D

substitution

oxidation

condensation

 

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11 mark

Xylitol is an artificial sweetener used in toothpastes and chewing gum to improve their taste without impairing dental hygiene.10-2-m-q1-ib-chemistry-mcqs

Which functional groups could be produced if Xylitol is oxidised under suitable conditions?

 

1

              alkene

2

              aldehyde

3

              carboxylic acid

4

              ketone

  • 1 only

  • 2 only

  • 2, 3 and 4

  • 2 and 4

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21 mark

Isomers X and Y both react with HBr.7KgQdxfW_10-2-m-q2-ib-chemistry-mcqs

 A mixture of X and Y is reacted with HBr.

Which three structures represent three different possible products of this reaction?

 A  

(CH3)2CHCBr3

   (CH3)2CBrCHBr2

 CH3CHBrCHBrCH3

B

(CH3)2CHCBr3

(CH3)2CBrCHBr2

CH3CBr2CHBrCH3

C

(CH3)2CBrCBr3

(CH3)2CHCBr3

CH3CBr2CHBrCH3

D

(CH3)2CBrCHBr2

CHBr2CBr(CH3)CH3

CH3CHBrCBr2CH3

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31 mark

In the presence of ultraviolet light, ethane and chlorine react to give a mixture of products.

Which compound could be present in the mixture of products?

  • CH3Cl

  • CH3CH2CH2Cl

  • CH3CH2CH2CH3

  • CH3CH2CH2CH2CH3

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41 mark

Dichlorodifluoromethane, CCl2F2, has been used in aerosol propellants and as a refrigerant.

Which statement helps to explain why dichlorodifluoromethane is chemically inert?

 

  • the carbon-fluorine bond energy is large

  • the carbon-fluorine bond has a low polarity

  • fluorine is highly electronegative

  • fluorine compounds are non-flammable

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51 mark

In the hydrolysis of bromoethane by aqueous sodium hydroxide, what is the nature of the attacking group and of the leaving group?

 

 

attacking group

leaving group

A

B

C

D

electrophile

electrophile

nucleophile

nucleophile

electrophile

nucleophile

electrophile

nucleophile

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61 mark

Which volume of oxygen measured at room temperature and pressure is needed for complete combustion of 0.1 mol of propane? (Molar volume = 24dm3 at rtp)

  • 12.0 dm3

  • 5.0 dm3

  • 20.0 dm3

  • 24.0 dm3

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71 mark

2.30 g of ethanol were mixed with aqueous acidified potassium dichromate(VI) and the desired organic product was collected by immediate distillation under gentle warming. The yield of the product was 50.0%. ( RAMs C= 12, H=1, O=16)

What mass of product was collected?

  • 1.10 g

  • 1.15 g

  • 2.20 g

  • 2.30 g

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81 mark

Which alcohol gives only one possible oxidation product when warmed with dilute acidified potassium dichromate(VI)?

  • butan-1-ol

  • butan-2-ol

  • 2-methylpropan-1-ol

  • 2-methylpropan-2-ol

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91 mark

Hydroxyethanal has the structural formula HOCH2CHO.

In an experiment hydroxyethanal is heated under reflux with an excess of acidified potassium dichromate(VI) until no further oxidation takes place.

What is the skeletal formula of the organic product formed in the experiment?10-2-m-q9-ib-chemistry-mcqs

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101 mark

The diagram shows the structure of ethanedioic acid.10-2-m-q10-ib-chemistry-mcqs

Ethanedioic acid reacts with ethanol in the presence of a few drops of concentrated sulfuric acid to form a diester. The molecular formula of the diester is C6H10O4.

What is the structural formula of the diester?

  • CH3CH2CO2CO2CH2CH3

  • CH3CH2OCOCO2CH2CH3

  • CH3CH2O2CO2CCH2CH3

  • CH3CO2CH2CH2OCOCH3

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111 mark

Compound Q has the formula CH3CH2CO2CH3

What is the name of compound Q and how does its boiling point compare with that of butanoic acid?

 

name of Q

boiling point compared to butanoic acid

A

B

C

D

methyl propanoate

propyl methanoate

methyl propanoate

propyl methanoate

lower

lower

higher

higher

 

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121 mark

How many ester compounds have the molecular formula C4H8O2?

  • 2

  • 3

  • 4

  • 5

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