Question 1

The following statements are about the reaction of NaOH(aq) with the three chloroalkanes shown.

CH3CH2CHCl CH3      (CH3)2CHCH2Cl      (CH3)3CCl

Which statement is correct?

  A  

(CH3)2CHCH2Cl reacts with NaOH(aq) by an SN2 mechanism

  B  

the tertiary chloroalkane reacts more quickly than the others because the carbon atom bonded to the Cl atom is more positive in this molecule

  C  

the Cl atoms in the three chloroalkanes are attacked by OH-

  D  

the molecular formula of the major product is C4H8 for each reaction

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Question 2

How many organic elimination products form when 2-bromobutane is heated with a concentrated solution of potassium hydroxide in ethanol?

  A  

1

  B  

2

  C  

3

  D  

4

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Question 3

Which of the following is a secondary halogenoalkane?

  A  

CH3CH2CHClCH3


  B  

(CH3)2CClCH3


  C  

CH2ClCH2CH2CH3


  D  

CH2ClCH2CH2CH2Cl


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Question 4

What is the mechanism and type of the reaction between ammonia and chloromethane?

  A  

electrophilic addition

  B  

nucleophilic addition

  C  

free radical substitution

  D  

nucleophilic substitution

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Question 5

An organic ion containing a carbon atom with a negative charge is called a carbanion.

An organic ion containing a carbon atom with a positive charge is called a carbocation.

The reaction between aqueous sodium hydroxide and 1-bromobutane proceeds by an SN2 mechanism.

What is the first step in the mechanism?

  A  

attack by a nucleophile on a carbon atom with a partial positive charge 

  B  

heterolytic bond fission followed by attack by an electrophile on a carbanion

  C  

heterolytic bond fission followed by attack by a nucleophile on a carbocation

  D  

homolytic bond fission followed by attack by a nucleophile on a carbocation

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Question 6

Which radical is most likely to form by the homolytic fission of one covalent bond in bromochloromethane, CH2BrCl?

  A  

•CH2Cl

  B  

•CH2Br

  C  

•CHBrCl 

  D  

•CH2BrCl

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Question 7

The formation of a carbocation from a halogenoalkane is an example of

  A  

homolytic fission

  B  

heterolytic fission

  C  

an initiation reaction

  D  

a propagation reaction

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Question 8

What describes the first step in the nucleophilic substitution reaction of ammonia with a halogenoalkane?

  A  

NHattacks the halogen atom

  B  

NH2- attacks the carbon atom next to the halogen

  C  

NHforms a bond with its lone pair to the carbon atom next to the halogen


  D  

the halogen atom is lost as a radical

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Question 9

Which statement correctly describes the boiling points of fluoroethane and iodoethane?

  A  

fluoroethane has the higher boiling point because it forms hydrogen bonds

  B  

fluoroethane has the higher boiling point because the C-F bond is stronger than C–I

  C  

iodoethane has the higher boiling point because it forms the stronger instantaneous dipole–induced dipole bonds

  D  

iodoethane has the higher boiling point because the C-I bond is less polar than C-F

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Question 10

When heated with NaOH(aq), 1-iodobutane is hydrolysed at amuch faster rate than 1-chlorobutane.

Which statement explains the different rates?

  A  

the C-I bond enthalpy is greater than the C-Cl bond enthalpy

  B  

the C-I bond is less polar than the C-Cl bond

  C  

the C-I bond has a C atom with a greater δ+ charge than in the C-Cl bond

  D  

the C-I bond requires less energy to break than the C-Cl bond

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Question 11

Which equation represents a termination step?

  A  

CH3CH2CH3 + Br• ➔ CH3CHCH3• + HBr

  B  

O3 + ClO• ➔ Cl• + 2O2

  C  

RO• + H2C=CH2 ➔ ROCH2CH2

  D  

CH3CFCl• + Cl• ➔ CH3CFCl2

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Question 12

Why are fluoroalkanes unreactive?

  A  

fluorine is highly electronegative

  B  

the F- ion is very stable

  C  

they are polar molecules

  D  

the C-F bond is very strong

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Question 13

Which equation represents a propagation step?

  A  

•CH2Cl + Cl• ➔ CH2Cl2

  B  

•CH3 + •CH3 ➔ C2H6

  C  

Cl2 ➔ Cl• + Cl•

  D  

CH3Cl + Cl• ➔ •CH2Cl + HCl

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Question 14

Which equation represents an initiation step?

  A  

CH3CH2CHBr• + Br2 ➔ CH3CH2CHBr2 + Br•

  B  

O3 + Cl• ➔ O2 + ClO•

  C  

RCH2CH2• + H2C=CH2 ➔ RCH2CH2CH2CH2

  D  

CH3CFCl2 ➔ CH3CFCl• + Cl•

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