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12.

4 EXTRA QUESTIONS ON HALOALKANES


1.

(a)

Give the structural formula of 2-bromo-3-methylbutane.

(1)

(b)

Write an equation for the reaction between 2-bromo-3-methylbutane and dilute aqueous
sodium hydroxide. Name the type of reaction taking place.
Equation .....................................................................................................................
.....................................................................................................................................
Type of reaction ..........................................................................................................
(2)

(c)

Two isomeric alkenes are formed when 2-bromo-3-methylbutane reacts with ethanolic
potassium hydroxide. Name the type of reaction occurring and state the role of the
reagent. Give the structural formulae of the two alkenes.
Type of reaction ..........................................................................................................
Role of reagent.............................................................................................................
Structural formula of alkene 1

Structural formula of alkene 2

(4)
(Total 7 marks)

Mill Hill High School

2.

(a)

A compound of carbon, hydrogen and nitrogen contains 61.0% of carbon and 15.3% of
hydrogen by mass.
(i)

Calculate the empirical formula of the compound.


...........................................................................................................................
...........................................................................................................................
...........................................................................................................................

(ii)

What other piece of data is required to deduce the molecular formula from the
empirical formula?
...........................................................................................................................

(iii)

If the molecular formula of the compound is the same as the empirical formula,
draw two possible structures of the compound.

(6)

(b)

Another compound containing only carbon, hydrogen and nitrogen can be hydrolysed to
form butanoic acid.
(i)

Draw the structure of this compound.

(ii)

Write an equation for the formation of this compound from 1-bromopropane.


...........................................................................................................................

(iii)

Give the conditions for the reaction in part (b)(ii).


...........................................................................................................................
(3)
(Total 9 marks)

3.

Classify the following reaction.


C H Br + KOH C H + KBr + H O
3 7
3 6
2
...............................................................................................................................
(1)
(Total 7 marks)

Mill Hill High School

4.

Bromoethane can be hydrolysed by warming with aqueous sodium hydroxide. Name and
outline a mechanism for this hydrolysis reaction.
Name............................................................................................................................
Mechanism

(Total 3 marks)

5.

(a)

When 3-bromo-2-methylpentane, (CH ) CHCHBrCH CH , reacts with aqueous


32
2 3
potassium hydroxide, an alcohol is formed.
(i)

Name the type of reaction taking place and give the role of the reagent.
Type of reaction. ..............................................................................................
Role of reagent. ................................................................................................

(ii)

Give the structure of the alcohol formed and outline a mechanism for its formation.
Structure of alcohol

Mechanism

(5)

Mill Hill High School

(b)

When 3-bromo-2-methylpentane reacts with ethanolic potassium hydroxide, two isomeric


alkenes are formed.
(i)

Name the type of reaction taking place and give the role of the reagent.
Type of reaction. ...............................................................................................
Role of reagent...................................................................................................

(ii)

One of the reaction products is 2-methylpent-2-ene. Give the structure of this


alkene and outline a mechanism for its formation.
Structure of alkene

Mechanism

(iii)

Give the structure of the second alkene which is also formed in this reaction. What
type of stereoisomerism is shown by this compound?
Structure of second alkene

Type of stereoisomerism. ....................................................................................


(8)
(Total 13 marks)

Mill Hill High School

6.

There are four structural isomers of molecular formula C H Br. The structural formulae
4 9
of two of these isomers are given below.

CH
C H

C
CH

B r
3

Isomer 1
(a)

CH CH CH CH Br
3 2 2 2
Isomer 2

Draw the structural formulae of the remaining two isomers.

Isomer 3

Isomer 4
(2)

(b)

Name and outline the mechanism involved in the reaction between isomer 2 and
potassium cyanide.
Name.................................................................................................................
Mechanism

(3)
(Total 5 marks)

Mill Hill High School

7.

When 3-bromo-3-methylpentane, CH CH CBr(CH )CH CH , is treated with aqueous


3 2
3
2 3
ethanolic potassium hydroxide, a mixture of 3-methylpentan-3-oI, 3-methylpent-2-ene and an
isomeric alkene is formed.
(a)

(i)

Name the type of mechanism occurring in the formation of 3-methylpentan-3-ol


from 3-bromo-3-methylpentane.
............................................................................................................................

(ii)

Why is it difficult to oxidise 3-methylpentan-3-ol?


............................................................................................................................
(2)

(b)

Name and outline a mechanism for the formation of 3-methlypent-2-ene in the above
reaction.
Name of mechanism ...................................................................................................
Mechanism

(4)

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(c)

Give the structure and name of the isomeric alkene formed together with
3-methylpent-2-ene in the above reaction.
Structure

Name ..........................................................................................................................
(2)
(Total 8 marks)

8.

(b)

A substitution reaction occurs when 2-bromopropane reacts with aqueous sodium


hydroxide.
(i)

Draw the structure of the organic product of this reaction and give its name.
Structure

Name ...........................................................................................................
(ii)

Name and outline the mechanism for this reaction.


Name of mechanism ......................................................................................
Mechanism

Mill Hill High School

(5)

(c)

Under different conditions, 2-bromopropane reacts with sodium hydroxide to produce


propene.
(i)

Name the mechanism for this reaction.


......................................................................................................................

(ii)

State the role of sodium hydroxide in this reaction.


......................................................................................................................
(2)
(Total 7 marks)

9.

(a)

Draw the structure of 2-bromo-3-methylbutane.


(1)

(b)

(i)

Draw the structure of methylbut-2-ene.

(ii)

Methylbut-2-ene is formed when 2-bromo-3-methylbutane is treated with ethanolic


potassium hydroxide. Name and outline the mechanism for this reaction.
Name of mechanism .........................................................................................
Mechanism
(5)

(c)

Name the isomer of methylbut-2-ene which is also formed when 2-bromo-3-methylbutane


is treated with ethanolic potassium hydroxide.

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.....................................................................................................................................
(1)
(Total 7 marks)

Mill Hill High School

10.

This question concerns the chemistry of ethene and compounds derived from it. Consider the
following statements and then answer the questions below.

Treatment of ethene with bromine gives a compound C.

Compound C may be converted in the laboratory into a compound D, which has a


percentage composition by mass of: C 38.71%; H 9.68%; O 51.61%. The relative
molecular mass, M , of D is 62.
r

(b)

Give the name of compound C.


.....................................................................................................................................
(1)

(d)

(i)

Use the analytical data provided at the start of the question to deduce the molecular
formula of compound D.

(3)

(ii)

Give the reagent(s) and condition(s) for the conversion of C into D.


Reagent(s) .........................................................................................................
Condition(s) ......................................................................................................
(2)

(iii)

Write an equation for the conversion of C into D.


...........................................................................................................................
(2)
(Total 8 marks)

Mill Hill High School

10

11.

Compound X, (CH ) CHCN, can be formed from a haloalkane, C H Br.


32
3 7
(i)

Name compound X.
...........................................................................................................................

(ii)

Give the reagent and conditions necessary to form X from C H Br.


3 7
Reagent..............................................................................................................
Conditions..........................................................................................................

(iii)

Name and outline the mechanism for this reaction, showing clearly the structure of
C H Br.
3 7
Name of mechanism..........................................................................................
Mechanism

(7)

(Total 7 marks)

Mill Hill High School

11

12.

(a)

When 3-bromo-2,3-dimethylpentane, (CH ) CHCBr(CH )CH CH3, reacts with aqueous


32
3
2
potassium hydroxide, an alcohol is formed.
(i)

Name the type of reaction taking place and give the role of the reagent.
Type of reaction ...............................................................................................
Role of reagent .................................................................................................

(iii)

Why is it difficult to oxidise this alcohol?


...................................................................................................................
(3)

(b)

When 3-bromo-2,3-dimethylpentane reacts with ethanolic potassium hydroxide, three


structurally isomeric alkenes are formed.
(i)

Name the type of reaction taking place and give the role of the reagent.
Type of reaction ...............................................................................................
Role of reagent .................................................................................................

(ii)

One of the reaction products is 2,3-dimethylpent-2-ene.


Give the structure of this alkene and outline a mechanism for its formation.
Structure of alkene

Mechanism

(iii)

Give the structures and names of the other two alkenes which are also formed.
Structure of second alkene

Name .................................................................................................................
Structure of third alkene

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12

Name .................................................................................................................
(10)
(Total 13 marks)

13.

Name the type of mechanism and write an equation for the reaction of bromoethane with
an excess of ammonia, showing clearly the structure of the organic product.
Type of mechanism ....................................................................................................
Equation

(3)

14.

(a)

(i)

Write an equation for the reaction between 1-bromopropane and potassium cyanide.
...........................................................................................................................
(1)

(ii)

Give the name of the type of mechanism involved in the reaction in (b)(i).
...........................................................................................................................
(1)

(b)

Give the formula of the attacking species in this reaction and state what feature of its
structure is responsible for its role.
Formula ..........................................................................................................
Structural feature ............................................................................................
(2)
(Total 4 marks)

15.

(a)

Give the systematic chemical name of CCl F .


2 2
(1)

(b)

Draw the shape of the CCl F molecule. Explain this shape in terms of the electron pair
2 2
repulsion theory and suggest why the shape of the CCl F molecule is non-regular.
2 2
(3)

(c)

Suggest why, in the reaction represented by equation (5), a chlorine atom is lost rather
than a fluorine atom.
(1)
(Total 5 marks)

Mill Hill High School

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14

16.

Bromination of 3-methylpentane gives a mixture which contains four different structural


isomers, one of which is 3-bromo-3-methylpentane.
(a)

Give the structures and names of the other three structural isomers.
(6)

(b)

In aqueous ethanolic KOH, 3-bromo-3-methylpentane can undergo substitution to form an


alcohol or elimination to produce a mixture of two alkenes. One of the alkenes formed
exhibits geometrical isomerism. Give the structures and names of the compounds formed.
Account for the formation of the various products by reference to the mechanisms of the
reactions involved.
(15)
(Total 21 marks)

Mill Hill High School

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