CHEM110/Block 4/Functional Groups I//2019 1

CHEM110 2019
CHEMISTRY OF THE LIVING WORLD

BLOCK 4: FUNCTIONAL GROUPS I

Lecturer: Dr Kaitlin Beare (KDB)

email: CHEM110@auckland.ac.nz

This handout should be brought to all lectures.

Please fill in the section below. Should you misplace this handout it will assist us in returning it
to you. Anyone finding this handout should take it to Chemistry Reception, Level 6 of Building
302 (Science Centre).

Name:

Laboratory Day and Time: Bench Number:

At the end of block 4, you should be able to:

• Write chemical equations for common reactions of alkenes, alkynes, alkyl halides, benzene
and simple benzine derivatives, including appropriate reagents.
• Write appropriate mechanisms for electrophilic addition, nucleophilic substitution,
elimination and electrophilic aromatic substitution reactions.
• Use resonance to explain the unusual reactivity of benzene and its derivatives.
• Use mechanistic reasoning to predict/explain regiochemistry or stereochemistry in
electrophilic addition, nucleophilic substitution, elimination and electrophilic aromatic
substitution reactions.
• Predict the outcome of reactions where nucleophilic substitution and/or elimination
mechanisms are in competition with each other.
• Suggest routes for synthesising simple organic molecules using the reaction types described
above.

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 CHEM110/Block 4/Functional Groups I/2019 2

Pre-Lecture Reading - Lecture 1

1. ALKENES
Khan academy videos (Block 1 Revision) - Links on Canvas, Block 4.
Naming alkenes: naming alkene examples: https://www.khanacademy.org/science/
organic-chemistry/alkenes-alkynes/naming-alkenes/v/naming-alkenes-examples

Naming alkenes: cis-trans and E-Z naming scheme for alkenes: https://www.khanacademy.
org/science/organic-chemistry/alkenes-alkynes/naming-alkenes/v/cis-trans-and-e-z-
naming-scheme-for-alkenes

Naming alkenes: Entgegen-Zusammen naming scheme for alkenes examples: https://

www.khanacademy.org/science/organic-chemistry/alkenes-alkynes/naming-alkenes/v/
entgegen-zusammen-naming-scheme-for-alkenes-examples

The functional group in Alkenes is comprised of two carbon-carbon bonds, one of which is
a sigma (σ) bond and the second is a π-bond. The carbons are sp2 hybridised, which means
the double bond is planar, with bond angles of approximately 120o. The alkene double bond
is considered electron-rich as it contains 2 electrons in the σ-bond, and two electrons in the
π-bond.

C C ~120o

the reactive site

Alkenes contain at least one double bond: as they have fewer hydrogens per carbon than related
alkanes they are referred to as UNSATURATED.

Preparations of alkenes – these are usually via elimination reactions.

(a) Acid-catalysed dehydration of

(removal of H2O from) alcohols.
(Reagent: concentrated H2SO4)

(b) Base promoted dehydrohalogenation of

(removal of HX from) alkyl halides.
(Reagent: KOH or NaOH in ethanol)

Practice Question Draw the alkene products of the following reactions.

-H O
2
a) HO

Br
- HBr

b)

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 CHEM110/Block 4/Functional Groups I//2019 3
1.2 Alkene Preparation
As noted in the pre-reading, the methods of alkene formation rely upon elimination of either
H2O from an alcohol, or elimination of HX from an alkyl halide. Where more than one alkene can
be formed, the Saytzeff (Zaitsev) rule applies.

Saytzeff rule: The major product is the most substituted alkene; that is the alkene with the
least number of hydrogens directly attached to the carbons of the C=C.

Examples: OH
conc. H2SO4
CH3 CH2 CHCH2 CH3

KOH
CH3 CH2 CH2 CH2 CH2 Br
ethanol

OH
conc. H2SO4
CH3 CHCHCH3
CH3

Practice Question:

A CH3-CH=CH-CH3

vs

B CH2=CH-CH2-CH3 C D

1.3 Reactions
The double bond of an alkene is electron rich (acts as a nucleophile). Generally undergo addition
reactions.
C C + C C

1.3.1 Hydrogenation.
(Reagent: H2/catalyst (e.g. Pt))

sometimes this is called a reduction. C C

C C +

Occurs with syn stereochemistry

Me Me
cis-1,2-dimethylcyclopentane

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 CHEM110/Block 4/Functional Groups I/2019 4
1.3.2 Reactions initiated by addition of an electrophile E+.
(a) H+ as an electrophile
Overall, addition of HZ (Z = halogen, OH, OR) via a carbocation intermediate.

C C C C C C

C C

Where more than one product can be formed, Markownikoff’s rule applies.

Markownikoff’s rule
Addition of an unsymmetrical reagent to an unsymmetrical alkene, gives as the major product
the compound in which the electropositive part of the reagent (usually H+) has bonded to the
carbon of the C=C that is directly bonded to the greater number of hydrogen atoms.

Examples of HZ addition:

CH3CH CHCH3 +

CH3CH CH2

We can get an understanding of why Markownikoff’s rule “works” by consideration of the

reaction mechanism. For the reagents considered here:
Mechanism:
(i) Addition of H+ to C=C

C C C C

(ii) Addition of nucleophile

(Cl−, H2O etc) to the carbocation.

C C
H

C C
H

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 CHEM110/Block 4/Functional Groups I//2019 5
For CH3CH=CH2 + HCl, there are two possible carbocations in step (i).

CH3 CH CH2

The carbocation from (a) gives 1-chloropropane (the minor product), whereas the carbocation
from (b) gives 2-chloropropane (the major product).

The carbocation from (a) is The carbocation from (b) is

The carbocation from (b) is more stable (recall Block 1, Unit 4). It is more readily formed, so
more of the product from route (b) is formed.

An alkenes summary sheet is available on Canvas

Practice Question What two different alkenes, upon reaction with aqueous acid, would give
the alcohol shown?
OH

A B

(b) Halogenation.
(Reagent: Br2, Cl2) Overall: C C + Br2 C C

Mechanism:
(i) Halogen acts as an electrophile.

C C

(ii) Halide ion acts as a nucleophile. C C

Br
Note: 1. Occurs with anti stereochemistry.

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 CHEM110/Block 4/Functional Groups I/2019 6
To explain this requires refinement of the earlier mechanism.
trans-1,2-dibromocyclopentane

bromonium ion
intermediate

Other nucleophiles, if present, can compete and give different products.

Br2
e.g. CH3 CH CHCH3 H O
2

Discharge of Br2 colour is often used as a lab test to detect alkenes.

Pre-Lecture Reading - Lecture 2

ALKYNES sp
a) Introduction.
The functional group is: Nomenclature: suffix yne
a σ-bond and two π-bonds.
Example: CH3CH2CH2CHC CCH2CH3
CH2CH3

b) Preparation.
Via didehydrohalogenation of dihaloalkanes.
(Reagent: KOH or NaOH in ethanol) H H H
C C C C C C
Br Br Br

Note: the way the 1,2-dibromoalkane (above) is drawn does not mean it was made via cis-
addition of Br2 to an alkene. Br2 always adds trans to an alkene – in this case the molecule has
been allowed to rotate to this view to highlight how 2 moles of HBr can be removed to form an
alkyne.

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 CHEM110/Block 4/Functional Groups I//2019 7

AROMATIC COMPOUNDS
a) Introduction.
The parent compound is benzene, molecular formula C6H6, which represents 4 DBE’s. Some
early proposals for its structure included:
H H
H H H H

H H H H
H H
Dewar Ladenberg Kekulé (1865)

Kekulé proposed oscillation of double bonds. Kekule’s proposed structure answered a lot of
observations, including that all carbon-carbon bond lengths are the same, and that benzene
does not undergo reactions typical of alkenes.

Resonance gives the answer.

orbital picture of benzene

resonance contributors

The ‘true’ structure is the resonance hybrid

(somewhere in-between). Sometimes drawn as:

b) Resonance energy of benzene.

The conjugated double bonds present in the structure of benzene give it an extra stability –
this stability is referred to as the ‘resonance energy’. It is this extra stability versus non-conju-
gated double bonds that makes benzene react in a different way compared to regular alkenes.
For example aromatic rings are not hydrogenated under the conditions used for alkenes.

c) Cyclic hydrocarbons and aromaticity.

Cyclic hydrocarbons are aromatic if they contain (4N + 2)π electrons, where N is an integer
(whole number). In the case of benzene, 3 π-bonds contain 6 π-electrons which satisfies the
equation for N=1. The resonance energy of benzene is 155 kJ mol-1.

Other examples of aromatic compounds include:

10 π-electrons (N= 2)
resonance energy: 255 kJ mol-1

(5 resonance contributors not shown)

14 π-electrons (N=3)
cf resonance energy: 349 kJ mol-1

In comparison, cyclobutadiene is a cyclic hydrocarbon but it has only 4-π electrons in the ring
– it is termed ‘anti-aromatic’ and behaves as an alkene i.e. addition chemistry.

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 CHEM110/Block 4/Functional Groups I/2019 8

d) Nomenclature.
Br NO2
i) Monosubstituted benzenes.
Generally substituent name plus benzene. Examples:
bromobenzene nitrobenzene
NH2 CHO CO2H OH CH3
Some compounds generally
known by trivial names are:

aniline benzaldehyde benzoic acid phenol toluene

The following are all representations for
the phenyl (Ph) i.e. substituted benzene,
group.

ii) Disubstituted.
G G G G
ortho ortho Y
meta meta Y
para ortho meta
Y
para
(o) 1,2- (m) 1,3- (p) 1,4-
iii) >Disubstituted.
Cl
Use the lowest possible sum of Example:
numbers for the substituents.
O2N 4-chloro-1,2-dinitrobenzene
NO2

Practice Question Which compounds shown to the right would hydrogenate with H2/Pt at 25
°C?

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 CHEM110/Block 4/Functional Groups I//2019 9
2. ALKYNES.
2.1 Reactions.
Alkynes generally undergo addition reactions, just like alkenes.

2.1.1 Hydrogenation.
The reagent(s) used depends on the number of mole equivalents of H2 one wishes to add, and
the required stereochemistry of H2 addition.
Example:

CH3CH2C CCH3

C C
C C

2.1.2 Electrophilic addition of HX and X2

Note: 1. Markownikoff’s rule followed for HX addition.
2. Reaction can be stopped after addition of one mole equivalent of reagent.
3. Anti stereochemistry of addition is observed.

2.1.3 Addition of water - hydration (Reagent: aq. H2SO4/HgSO4)

Note: 1. Addition of only one mole equivalent of water occurs.
2. For all alkynes, except ethyne, the product(s) is(are) ketones.
Example:
CH3C CH

Presuming Markownikoff addition

expect formation of:

This is a tautomeric equilibrium.

The species involved are tautomers.

2.1.4 Formation of alkynide anions from terminal alkynes (RC≡C-H).

The hydrogen on a terminal alkyne sp carbon is weakly acidic and can be removed with a strong
base. The carbon nucleophile (alkynide anion) formed is useful in synthesis for carbon chain
extension.

Na+NH2
-
CH3CH2Br
RC CH RC C RC CCH2CH3

An alkynes ‘summary’ sheet is available on Canvas.

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 CHEM110/Block 4/Functional Groups I/2019 10
3. AROMATIC COMPOUNDS.
3.1 Reactions.
Whereas alkenes undergo
Br H Br
addition reactions, benzene H Br
and substituted benzenes usually
undergo substitution reactions. This is because aromatic compounds, like benzene, have the
extra stability of ‘resonance energy’ which essentially ‘prevents’ aromatic compounds from
doing addition reaction chemistry.

3.1.1. Preparation of monosubstituted benzenes.

Generally: + +

Mechanism:
+ E+

addition

H H H H
E E E + E
resonance stabilized cation resonance hybrid
elimination

E
+

(a) Generation of electrophiles.

The electrophiles are usually formed by catalytic action.
Halogenation
Cl Cl + FeCl3

No catalyst is needed if a very electron rich aromatic compound is being halogenated.

Nitration
HNO3 + H2SO4

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 CHEM110/Block 4/Functional Groups I//2019 11
Friedel-Crafts acylation and alkylation
Acylation
R O
1. C
O
R C X + AlX3
2. -H

Alkylation
RX + AlX3 R = X=

Thus CH3CHCH3 + AlCl3

Cl 1. 2. -H+

CH3 CH3
CH

However, in presence
of AlCl3:
+ CH3CH2CH2Cl

Why? CH3CH2CH2Cl + AlCl3

Pre-Lecture Reading - Lecture 3

1. Review the general reaction for electrophilic aromatic substitution (section 3.1.1).
2. Watch the Khan Academy video on electrophilic aromatic substitution:
https://www.khanacademy.org/science/organic-chemistry/aromatic-compounds/reac-
tions-benzene/v/electrophilic-aromatic-substitution (Link on Canvas, Block 4).

Practice Question For the following, give the product of the reaction, or give the missing
reagents:

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 CHEM110/Block 4/Functional Groups I/2019 12
(b) Introduction of a substituent onto an aromatic ring.
(i) A summary of reagents for the direct introduction of substituents and modification of
the nitro group to form the diazonium ion is given below:

(ii) A summary of the preparation and reagents for the subsequent modification of
the diazonium ion and the compounds formed is given below.

NO2 NH2 N N OH
+
H 3O

(see previous scheme for these reagents) CuCN phenol

O Cl
C CO2H CN
+
acid SOCl2 H 3O
derivatives

(c) Drawing reaction schemes for preparation of monosubstituted benzenes.

Examples:
(i) (ii)

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 CHEM110/Block 4/Functional Groups I//2019 13
3.1.2 Preparation of disubstituted benzenes.

G G
+
+ + H

All positions around the ring are no longer

equivalent, and substitution can occur,
ortho, meta or para to G.

controls position of incoming

electrophile.

Need to consider:
(i) Where will substitution occur?
(ii) Will the reaction occur more or less readily than for the same electrophile with benzene?

(a) The reaction of toluene with various electrophiles.

Experimental data: % ortho % meta % para
Bromination 32.9 0.3 66.8
Nitration 58.4 4.4 37.2
Chlorination 59.8 0.5 39.7
Methylation 55.7 9.9 34.4
Other studies show that toluene is approximately 10 - 20 times more reactive than benzene…
From this we can deduce:
CH3
+
+ E

(b) Summary of directing & activating power of substituents.

Substituents fall into two categories.
(i) ortho-para directors

strongly activating weakly activating deactivating

Oxygen, nitrogen and halogens all have unshared electron pair(s) which can be donated into
the aromatic ring (by resonance). Alkyl groups can also donate electrons into the ring (pro-
cess called induction).

(ii) meta directors

strongly deactivating moderately deactivating

All groups have a multiple bond to the atom that is bonded to the aromatic ring sp2 carbon.
All groups have the electropositive end of a polar bond attached to the aromatic ring carbon.

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 CHEM110/Block 4/Functional Groups I/2019 14
(c) Explanation of substituent directing power.
The directing power of a particular substituent can be rationalised by consideration of the
possible Wheland intermediates in the electrophilic aromatic substitution mechanism.
(i) electrophilic attack when an ortho-para director is attached. Consider phenol with E+.

For ortho substitution
OH OH OH OH OH OH
+
E E E E E
+ E H H H H + H
+

For meta substitution [No charge delocalisation by oxygen.]

OH OH OH OH OH
+
+ E E E E + H
+

H H H E

For para substitution

In general it is found that more of the product(s) is(are) formed from the pathway(s) where
one can draw the largest number of ‘reasonable’ resonance contributors for the carbocation
intermediate.

ii) electrophilic attack when a meta director is attached. Consider nitrobenzene with E+.
For ortho substitution
O O O O O O
NO2 N N N NO2
+
E E E E
+ E H H H + H+

For meta substitution O

O O O O O
NO2 N N N NO2
+
+ E E E E + H+
H H H E

For para substitution

Hence:

Practice Question

H NO2

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 CHEM110/Block 4/Functional Groups I//2019 15

Pre-Lecture Reading - Lecture 4

sp3
4. ALKYL HALIDES alkyl halide
Alkyl halides are compounds that contain a halo-
C X
gen attached to an sp3 hybridised (alkyl) carbon,
as opposed to an sp2 carbon (eg aryl halides, vinyl X
halides). X C C

aryl halide vinyl halide

Classification and nomenclature.
Alkyl halides are classified as: 1° 2° 3° (primary, secondary, tertiary)
1 2 3 groups (alkyl or aryl) bonded to C-X
Named systematically as a haloalkane.
Examples:
CH3 CH3 I
CH3CHCH2Cl CH3CBr CH3CH2CHCH3 CH2Br
1-chloro-2-methylpropane CH3 2-iodobutane
(primary) 2-bromo-2-methylpropane (secondary) benzylbromide
(tertiary) (primary)

Preparations.
a) Addition of HX (or X2) to an alkene. H X
Markovnikov’s rule applies. C C + HX C C

Example:
HBr
+ Br
Br
major minor

Mechanism:
A racemic mixture (50:50) of (S) and (R) -2-bromobutane is formed as the major product.
The term ‘racemic mixture’ is important – we will be referring to it a few times in the next
lecture.

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 CHEM110/Block 4/Functional Groups I/2019 16

b) From an alcohol.

ROH + SOCl2 →
RCl As you will see in Block 4, SOCl2
is the preferred reagent for 1°
R3COH + HX
→ R3CX + H2O and 2° alkyl halides, HCl for 3°
halides.
X = Cl or Br

Practice Question Name and classify the following alkylhalides:

CH3 Br
CH3CH2CH2Cl CH3CH I CH3CH2CH2CCH2CH3 CH3Br
CH3

4.1 Reactions.
4.1.1 Substitution.

One can replace the halogen of a 1°, 2°, or 3° alkyl halide with an appropriate nucleophile.
Cl− Br− I−

Overall: C
+ C X + X

C H 3 C C + C H 3 B r

C H 3 C H 2 B r + C N

C H 3O
+ C H 3B r

4.1.1.1 Mechanisms of Substitution.

Kinetics experiments reveal two extremes of mechanism, which are illustrated by:
(a) (CH3)3CBr → (CH3)3COH and (b) CH3Br → CH3OH

(a) SN1 unimolecular mechanism: Rate ∝

Strength (kinetic description; fast/slow) of nucleophile does not affect the rate of SN1, but
the strength/basicity of the nucleophile may affect the course of the reaction, for example,
favouring elimination.
Favoured when intermediate carbocation, from breaking the C-X bond, is “relatively stable”.

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 CHEM110/Block 4/Functional Groups I//2019 17
Mechanism:
(CH3)3C Br
+
(CH3)3C + H2O
Reaction energy profile:
Thus for an SN1 reaction we have substitution by a
nucleophile, with only one species involved in the r.d.s
(when the leaving group departs).
Energy
Stereochemistry:
Cl OH
H2O
For PhCHCH3 PhCHCH3 Reaction progress
Experiments show:

Why?

(a) SN2 bimolecular mechanism: Rate ∝

_
Mechanism: Nu + CH3 Br

Reaction energy profile:

Thus for an SN2 reaction we have substitution by a
nucleophile, with two species involved in the r.d.s.

Stereochemistry Energy
When a chiral non-racemic secondary alkyl halide reacts
via an SN2 pathway, a chiral non- racemic (optically active)
product results from inversion of configuration. Reaction progress
) (
) (
) (

CH3 CH3
CH3
H C Br C Br C H
CH3CH2 CH2CH3
H CH2CH3

From a 1° to a 2° to a 3° alkyl halide, the transition state becomes more crowded. This raises the
energy of the transition state and hence the activation energy for the reaction.

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 CHEM110/Block 4/Functional Groups I/2019 18

Pre-Lecture Reading - Lecture 5

1. Review the general reactions given in block 1 of the course notes, particularly with
reference to alkenes.
2. Review pre-reading for lecture 1 of this block (4) and review the first half of block 4
lecture 1

Practice Question: The following alkyl bromide can undergo both substitution and elimination
reactions. Give the structures of the two possible products.

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 CHEM110/Block 4/Functional Groups I//2019 19
E1 and SN1 can compete, leading to product mixtures:
CH3
-
slow (-Br )
CH3CH2C Br
65° EtOH
CH3

Zaitsev (Saytzeff) rule applies where more than one alkene can be formed.

(a) E2 bimolecular mechanism. Rate ∝

_
B
_
C C C C BH + C C + X

The proton is removed, the C=C is formed, and the C-X bond is broken, all in a single (concerted)
step.

Requires a strong base.

Can be observed for 1° if product extends conjugation e.g. PhCH2CH2X → PhCH=CH2.

Zaitsev (Saytzeff) rule applies where more than one alkene can be formed.

4.2 Substitution vs Elimination summary

The table indicates whether substitution or elimination is likely to be the major reaction, on the
basis of alkyl halide type (primary, secondary, tertiary) and reagent type (nucleophile or base).
Alkyl Halide Reagent Type
Weak nucleophile, Stronger nucleophile, low Stronger nucleophile,
neutral* basicity** high basicity***
Primary

Secondary

Tertiary

*Examples: H2O, CH3OH, **Examples: Cl−, Br−, I−, CN-, ***Examples: HO−, CH3O−,
CH3CH2OH CH3S-, CH3COO- CH3CH2O−, H3N, (CH3)3N, H2N-

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 CHEM110/Block 4/Functional Groups I/2019 20
For:
CH3O + CH3CH2Br

(CH3)3CO + CH3Br

but CH3O + (CH3)3CBr

And contrast the reactivity of halogen bonded to sp2 carbon in an aryl halide.
Whereas:

O + CH3Br OCH3

Br + CH3O NO REACTION

Vinyl halides can undergo elimination reactions with strong bases, to form an alkyne.

4.3 Formation of Grignard Reagents.

Alkyl halides and aryl halides form Grignard reagents on treatment with Mg in dry diethyl ether
as solvent.

Magnesium is electropositive, and therefore the attached carbon in the Grignard reagent can
be regarded as a carbanion (R–). Thus a Grignard reagent can act as a carbon nucleophile (or
as a base). Some reactions of Grignard reagents as carbon nucleophiles will be covered later
in the course.

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 CHEM110/Block 4/Functional Groups I//2019 21
REVISION EXERCISES FOR BLOCK 4

1. Write equations showing the product(s) for each of these reactions:

a) but-2-ene + HCl
b) 1-chloro-2-methylcyclohexene + H2/Pt
c) cyclopentene + H+ followed by water
d) 1,2-dimethylcyclohexene + Cl2

2. Write the structures for the two carbocations which could be formed by the addition of
a proton to the following alkenes. State which cation you would expect to be the most
stable intermediate.
CH3
a) CH2 CHCH2CHCH3 b) c) CH2 C(CH3)2
CH3

3. Write equations for the following reactions, labelling both major and minor products as
necessary. Give the mechanism for formation of the (major) product.
a) pent-1-ene + H+ followed by water
b) 2-phenylbut-2-ene + HCl
c) 1,2-dimethylcyclopentene + Br2

4. Write the product structures, and label as the major or minor products, for each of the
following reactions.
CH3 CH3
a) CH3CHCH2CH2CH3 Hheat c) CH3CHCH2CHCHCH3 heat
2 SO 4 NaOH
OH Cl
Cl
b) (CH3)2CCH2CH3 Hheat d) heat
CCH2CH3 NaOH
2 SO 4
OH CH(CH3)2
5. Using but-2-yne as the only organic starting material, along with any inorganic reagents
needed, how would you synthesize the following compounds? More than one step may
be needed. Show structures of any minor products formed.
a) Z-but-2-ene d) 2,2,3,3-tetrabromobutane
b) 2-bromobutane e) E-but-2-ene
c) butanone
CH3 H NO 2
6. Give the structure for the resonance
contributor arising from the electron
movement as indicated by the curly O-
arrows. N
O

7. Give the predominant product(s) of the following reactions:

a) Toluene (methylbenzene) + conc. HNO3/H2SO4
b) 4-Methylaniline with HNO2 at 0°C, followed by addition of CuCN
c) 2-Methylaniline with HNO2 at 0°C, followed by addition of H3O+
d) Benzaldehyde + conc. HNO3/H2SO4

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 CHEM110/Block 4/Functional Groups I/2019 22
8. For each of the following predict whether the reaction proceeds by an SN1 or SN2
mechanism.
a) CH3CH2I + HO−
b) (CH3)3CBr + H2O
c) (CH3)2CHBr + HO−

9. Which of the following SN2 reactions would you expect to go faster?

a) Reaction of CN− with CH3CHBrCH3 or with CH3CH2CH2Br.
b) Reaction of I− with (CH3)2CHCH2CH2Cl or with H2C=CHCl.

10. Which of the following would you expect to react faster if the reaction proceeded by an
SN1 mechanism?
a) CH3Br or (CH3)3CBr with water.
b) CH3(CH2)6Br or PhCH2Br with water.

11. Assuming an SN2 reaction mechanism for the reaction of the following nucleophiles with
R-2-bromooctane, draw the structure of the product and indicate its configuration.
a) CN− b) CH3CO2−

12. What effect would your expect a change of leaving group from bromide to chloride to
have on the rate of an E1 reaction?

13. Suggest suitable reactants for the preparation of the following ethers:
a) CH3OCH2CH3 c) (CH3)3COCH3

b) (CH3)2CHOCH2CH2CH3 d) OCH2CH2CH3

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