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TAMPINES JUNIOR COLLEGE

2014 JC1 Chemistry Tutorial


H2 Level Alkenes
Review Questions (For self-revision; to be completed BEFORE tutorial lesson; answers on LMS)
1. Introduction to Alkenes
Functional
Group

Type of
hydrocarbo
n

Type of
hybridization

Shape with
respect to each
C=C atom

General
Formula for
non-cyclic
alkenes

General
Formula for
cyclic
alkenes

2. Oxidation
Mild Oxidation

Vigorous Oxidation

Conditions
Possible Products

Note: Temperature is more important than pH in determining if the reaction undergoes mild or vigorous oxidation

Example:
(a)

CH2 = C(CH3) CH = CH CH = C(CH3)2

Cold, alkaline,
KMnO4(aq)

(b)

CH2 = C(CH3) CH = CH CH = C(CH3)2

hot, acidified
KMnO4(aq)

3. Electrophilic Addition
Br2 reacts with propene via electrophilic addition. The overall equation is given below:
TPJC/ 2014 H2 CHEM/alkenes / 1

CH3CH=CH2 + Br2

CH3CHBrCH2Br

Complete the mechanism for this reaction, including curly arrows showing the movement of
electrons, and all charges
Step 1:

slow
CH3CH

CH2

CH3CH

Step 2:

CH2

Br-

Br

CH3CH

CH2

fast

CH3CH

Br

Br

CH2
Br

4. Markovnikovs rule
Markovnikovs rule states that the .. part of the reagent (e.g.+H - OH-) will attach itself
to the carbon atom of the C=C double bond having the number of
. atoms bonded to it.
Example:
CH3CH=CH2 + +H - OH-(g)

KM

Complete the following:


nO
4
(a
q)

H2(g)
heat, Ni

H2O(g)
300 oC, 60 atm, H3PO4

nO4(aq)
cold, alkaline KM

ho
t,
a
c
id
if
ed

5.

CH3CH=CH2

dry HBr(g)

excess air / O2 (g)

Br2(aq)

Discussion Questions
TPJC/ 2014 H2 CHEM/alkenes / 2

Br2 (l)
CCl4

(To be attempted PRIOR to tutorial lesson; will be discussed during lesson; be ready to present your
answers)

1. The bond lengths in buta-1,3-diene differ from those which might be expected.
The carbon-carbon bond length in ethane is 0.154 nm and in ethene is 0.134 nm. The
central single bond in buta-1,3-diene (C2-C3), however, is shorter than the single bond in
ethane: it is 0.147 nm.
1
CH2

2
CH

0.134 nm

3
CH

0.147 nm

4
CH2
0.134 nm

Consider the hybridisation of the carbon


atoms in
(a) ethane and (b) ethene.
Which carbon-carbon bond length is
shorter? Why?

What helps to explain this C2-C3 bond length?


A
B
C
D

It is an sp2-sp2 overlap.
It is an sp2-sp3 overlap.
The electrons in the filled p orbitals on C2 and C3 repel each other.
The sp3-sp3 bonding is pulled shorter by a p-p (-bond) overlap.

[A-level, 2008]

2. Limonene, C10H16, occurs naturally in the pith oil of citrus fruits. Because it is readily
extracted from orange peel, it is a cheap by-product of the manufacture of orange juice.

limonene
Apart from its use as a starting material for synthesizing other oils and perfumes,
limonene itself is a useful solvent for oils and fats, and is therefore used as a degreaser
for metal components and also as a hand cleanser in workshops.
(a) What type(s) of stereoisomerism can limonene exhibit, and how many stereoisomers
of each type are there?
[2]
What types of stereoisomers have you learned
so far? Are they present in limonene?

(b) Draw the structural formulae of the products obtained when limonene is treated with
an excess of hot concentrated manganate (VII) ions.
[2]
What type of reaction is this?
What would your answer be if hot alkaline manganate(VII) had been used instead?

(c) Given that the addition of HBr to propene produces 2-bromopropane rather than
1-bromopropane, predict the structure of the product formed when limonene reacts
with an excess of HBr.
[2]
Apply Markovnikovs rule!

TPJC/ 2014 H2 CHEM/alkenes / 3

[A-level, 2013]

3. The diagram shows the structure of the naturally-occurring molecule cholesterol.


H3C
CH3
CH3
H

H
H

HO

cholesterol
Cholesterol reacts with cold, dilute acidified KMnO4.
Four students made claims about this reaction.
W
X
Y
Z

The cyclohexene ring becomes saturated.


The cyclohexene ring is broken open.
The number of chiral centres increases by 1.
The number of chiral centres increases by 2.

Which students claims are correct?


A

W and Y

W and Z

X and Y

X and Z
[A-level, 2012]

4. Ethane-1,2-diol may be formed by bubbling gas A through cold, dilute, acidified KMnO4.
(a) What is the identity of gas A?
(b) What would be observed during this reaction?

[1]
[1]
[A-level, 2008]

5. Potassium manganate(VII), KMnO4, in acidic or alkaline solution, is widely used as an


oxidising agent in organic and inorganic chemistry.
Draw the structure of the organic compound formed when the following compound is
heated under reflux with concentrated alkaline KMnO4, followed by acidification.
CH3
CHCH=CH2
CH3

Identify the terminal carbon. What will


happen to it under strong oxidation? What
are the conditions for strong oxidation?

[1]
TPJC/ 2014 H2 CHEM/alkenes / 4

[A-level, 2008]

6. Describe simple laboratory test/tests to distinguish the following pairs of organic


compounds. Give a balanced equation for any reaction that occurs.
(a) cyclohexane and cyclohexene
(b) but-1-ene and but-2-ene
7. Hydrogen iodide undergoes an addition reaction with propene forming 2-iodopropane.
When propene is bubbled through iodine monochloride, ICl, dissolved in a suitable
solvent, a similar reaction occurs.
Which product will be present in the greatest yield?
A
B
C
D

Apply Markovnikovs rule!

CH3CHClCH2Cl
CH3CHICH2I
CH3CHClCH2I
CH3CHICH2Cl

[A-level, 2013]

8. The equation represents a reaction.


+ Br2

Br

polar solvent

What is the purpose of the


polar solvent? Does it
participate in the reaction?

Br
Which statement about this reaction is correct?
A

Bromine acts as an electrophile.

It is a free-radical reaction.

It is a nucleophilic addition reaction.

It only takes place in the dark.


[A-level, 2009]

9. The halogens Cl2 and Br2 readily react with ethene as follows.
CH2=CH2 + X2

XCH2CH2X

(X = Cl or Br)

Name the type of reaction and describe the mechanism for this reaction, including curly
arrows showing the movement of electrons, and all charges.
[3]
[A-level, 2008]

10. Compounds A and B have the same molecular formula C4H8 but different structural
formula. Deduce the structural formula of each compound from the information given
below.
(a) A, on vigorous oxidation gives only one organic product, CH3COOH.
(b) B, on oxidation forms propanoic acid, CH3CH2COOH and CO2.

The word Deduce implies


that some reasoning or
explanation is required.

Practice Questions [For self-practice; answers will be posted on LMS.]


TPJC/ 2014 H2 CHEM/alkenes / 5

1. Write structural formulae for the following compounds:


(a) 3-methylpent-1-ene

(b) 3-methylcyclopentene

(c) hepta-1,6-diene

(d) cis-1-bromopropene

(e) tetrafluoroethene

(f) trans-2,3-dichlorobut-2-ene

2. Draw displayed formulae and give systematic names to the following compounds.
(a) (CH3CH2)2C(CH3)CH=CH2
(c)

(b) trans-CH3CH=CHCH3

CH=CH2

3. A gaseous hydrocarbon has the composition by mass: C, 85.7% ; H, 14.3%.


(a) Calculate the empirical formula of the hydrocarbon.
(b) A 0.25 g sample of the hydrocarbon has a volume of 100 cm3 at s.t.p. Calculate the
relative molecular mass and the molecular formula of the hydrocarbon.
(c) Draw three possible displayed formulae for the hydrocarbon.
[At least one of the structures is that of an alkene.]

4.

CH3

CH3
C

H
3-methylpentene

H
propene

Give the structural formulae of the main organic products formed when the above
hydrocarbons react with:
(a) gaseous hydrogen bromide
(c) bromine water
(e) cold, alkaline KMnO4(aq)

(b) steam in the presence of a catalyst


(d) Br2 in CCl4
(f) hot, acidified KMnO4(aq)

5. Ethene can be oxidised to ethane-1,2-diol or reduced to ethane.


Suggest suitable reagents and conditions for each of these reactions. In what way are
these reactions similar to each other?
6. (a) A liquid sample of but-2-ene contains two isomers with different boiling points.
(i) Name the type of isomerism that was displayed by but-2-ene.
(ii) Draw and name the two isomers.
(b) Draw the structure of the two isomeric products obtained when but-1-ene is treated
with cold dilute KMnO4(aq).
7.

The following compound is derived from plant essential oil.


TPJC/ 2014 H2 CHEM/alkenes / 6

O
H2C
CH3
H3C

When the compound is reacted with Br2 in CCl4, how many chiral centres does the
major product have?
A 2
B 3
C 4
The structures of four isomers of C4H8 are shown below.
H
H
H3C
H
CH3

8.
H
C

CH2

H
CH2CH3

C
H3C

C
CH3

H3C

C
H

CH2

H3C

(a)

State which structures are cis-trans isomers.

(b)

When the four isomers react with steam to form products, there is a pair of optical
isomers among the products. Draw the displayed structures of the pair of optical
isomers formed.
(c) Draw displayed formulae of the carbon-containing products formed when D is
subjected to each of the following:
(i) very mild oxidation by cold, dilute manganate (VII) ions.
(ii) strong oxidation by hot, concentrated manganate (VII) ions.

Mastery Questions [Answers will be posted on LMS.]


1. Four hydrocarbons, AD, have the same molecular formula C6H12 but different structural
formulae. A on oxidation gives ethanoic acid and methylpropanoic acid. B and C are cistrans isomers, with B having a higher boiling than C. D reacts with bromine gas to yield
a product which has a chiral centre.
(a) Draw displayed formulae of compounds AD, and give the IUPAC name for each of
these compounds.
TPJC/ 2014 H2 CHEM/alkenes / 7

(b) Suggest why the boiling point of B is higher than C.


(c) Compound E was found to be having the same molecular formula as compounds
AD. However, compound E reacts differently when added to bromine in CCl4, as
compared to AD.
(i)

Suggest why E reacts differently with bromine from compounds AD.


(ii) It has been suggested that compound E is not as reactive compared to
compounds AD. Why do you think this is so?

----- End -----

TPJC/ 2014 H2 CHEM/alkenes / 8

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