Beruflich Dokumente
Kultur Dokumente
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)
Cold, alkaline,
KMnO4(aq)
(b)
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
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)
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
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!
[A-level, 2013]
H
H
HO
cholesterol
Cholesterol reacts with cold, dilute acidified KMnO4.
Four students made claims about this reaction.
W
X
Y
Z
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]
[1]
TPJC/ 2014 H2 CHEM/alkenes / 4
[A-level, 2008]
CH3CHClCH2Cl
CH3CHICH2I
CH3CHClCH2I
CH3CHICH2Cl
[A-level, 2013]
Br
polar solvent
Br
Which statement about this reaction is correct?
A
It is a free-radical reaction.
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.
(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
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)
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)
(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.