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CHE_202_lec-17[1]

The document discusses factors influencing SN1 reactions, including substrate stability, leaving group quality, nucleophile nature, and solvent effects. It explains how stable carbocations, particularly allylic and benzylic types, enhance reaction rates, and outlines the differences between SN1 and SN2 mechanisms. Additionally, it covers elimination reactions (E1, E2, E1cB), their mechanisms, and comparisons between these and substitution reactions.

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2 views

CHE_202_lec-17[1]

The document discusses factors influencing SN1 reactions, including substrate stability, leaving group quality, nucleophile nature, and solvent effects. It explains how stable carbocations, particularly allylic and benzylic types, enhance reaction rates, and outlines the differences between SN1 and SN2 mechanisms. Additionally, it covers elimination reactions (E1, E2, E1cB), their mechanisms, and comparisons between these and substitution reactions.

Uploaded by

sakhawat.hossain
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PDF, TXT or read online on Scribd
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Reactions of Alkyl Halides

Factors influencing SN1 reactions

Factors that can influence an


SN1 reaction:
(i) The substrate;
(ii)The leaving group;
(iii)The nucleophile;
(iv)The solvent.

Q1. Mention the factors that can influence an SN1 reaction.


Reactions of Alkyl Halides
Factors influencing SN1 reaction: (i) The substrate

Since the rate-limiting step in an SN1 reaction is the spontaneous, unimolecular dissociation
of the substrate to yield a carbocation, the reaction is favored whenever a stabilized
carbocation intermediate is formed. The more stable the carbocation intermediate, the
faster the SN1 reaction.

(The word benzylic means “next to


an aromatic ring.”)

Q1. Discuss how substrates can influence an SN1 reaction.


Q2. What are benzylic carbocations? Why are they unusually stable?
Reactions of Alkyl Halides
Factors influencing SN1 reaction: (i) The substrate
Why allylic and benzylic carbocations are unusually stable?
-Due to resonance forms.

Figure 11.12 Resonance forms of allylic and benzylic carbocations. The positive charge is delocalized over the π system in both.

Because of resonance stabilization, a primary allylic or benzylic carbocation is about as stable as a


secondary alkyl carbocation and a secondary allylic or benzylic carbocation is about as stable as a
tertiary alkyl carbocation.

Q1. Discuss how substrates can influence an SN1 reaction.


Q2. What are benzylic carbocations? Why are they unusually stable?
Reactions of Alkyl Halides
Factors influencing SN1 reaction: (ii) The leaving group
The best leaving groups are those that are most stable; that is, those that are the conjugate bases of
strong acids. The leaving group is directly involved in the rate-limiting step in SN1 reaction.

Q1. Discuss how the


leaving groups can
influence an SN1
https://slideplayer.com/slide/14893856/ reaction.
Reactions of Alkyl Halides
Factors influencing SN1 reaction: (iii) The nucleophile

Q1. Are SN1 reactions influenced by the nature of the nucleophile? Explain your answer.
Reactions of Alkyl Halides
Factors influencing SN1 reaction: (iv) The solvent
Solvent effects in the SN2 reaction are due largely to stabilization or destabilization of the nucleophile
reactant, while solvent effects in the SN1 reaction are due largely to stabilization or destabilization of
the transition state.

Q1. Why protic and


aprotic solvents favor
SN1 and SN2
reactions,
respectively?
Q2. Discuss the
different mechanisms
by which solvents
affect SN1 and SN2
reactions.
Reactions of Alkyl Halides
Factors influencing SN1 reaction: (iv) The solvent

Q1. Why protic and aprotic solvents favor SN1 and SN2
reactions, respectively?
Q2. Discuss the different mechanisms by which
solvents affect SN1 and SN2 reactions.
Reactions of Alkyl Halides
Comparison between SN1 and SN2 reactions

Q1. Compare between SN1 and SN2 reactions.


Reactions of Alkyl Halides
Elimination reactions
Two kinds of reactions can take place when a nucleophile/Lewis base reacts with an alkyl
halide. The nucleophile can either substitute for the halide by reaction at carbon or can
cause elimination of HX by reaction at a neighboring hydrogen:

https://slideplayer.com/slide/14893856/

Q1. Why are elimination reactions more complex than substitutions?


Reactions of Alkyl Halides
Elimination reactions

Q1. What is Zaitsev’s rule? Explain with examples.


Reactions of Alkyl Halides
Types of Elimination reactions: E1, E2, E1cb
Elimination reactions: There are three types of elimination reactions E1, E2, E1cB.
-E1, E2, E1cB differ in the timing of C-H and C-X bond breaking.

Q1. What are the different types of elimination reactions?


Q2. Schematically explain the differences among E1, E2, E1cB
elimination reactions.
Reactions of Alkyl Halides
E2 elimination reactions

E2 elimination reactions: The E2


reaction (for elimination, bimolecular)
occurs when an alkyl halide is treated
with a strong base, such as hydroxide
ion or alkoxide ion (RO-). It is the
most commonly occurring pathway
for elimination.

The E2 reaction takes place in one step


without intermediates.
As the base begins to abstract H+ from
a carbon next to the leaving group, the
C-H bond begins to break, a C=C
bond begins to form, and the leaving
group begins to depart, taking with it
the electron pair from the C-X bond.

Q1. Discuss the general mechanism of E2 elimination reactions.


Reactions of Alkyl Halides
E1 reaction

E1 eliminations begin with


the same unimolecular
dissociation to give a
carbocation that we saw in
the SN1 reaction, but the
dissociation is followed
by loss of H+ from the
adjacent carbon rather
than by substitution.

Q1. Explain the mechanism of an E1 reaction.


Reactions of Alkyl Halides
Simultaneous E1 and SN1 reactions

Q1. Give an example of a reaction where mixture of


substitution and elimination products can be obtained.
Comparing E1 and E2
 Strong base is needed for E2 but not for E1

 E2 is stereospecifc (Anti periplanar geometry specific), E1 is not (there is no geometric


requirement on the E1 reaction because the halide and the hydrogen are lost in separate steps)

 E1 gives Zaitsev orientation


Reactions of Alkyl Halides
Comparing E1 and E2 reaction mechanisms

https://www.pinterest.com/pin/213006257353992556/

Q1. Compare between E1 and E2 reaction mechanisms.


Identifying reactions following
SN1, SN2, E1, E2 mechanisms
Reactions of Alkyl Halides
Comparison among E1, SN1, E2, SN2 reaction mechanisms
Reactions of Alkyl Halides
Comparison among E1, SN1, E2, SN2 reaction mechanisms
Reactions of Alkyl Halides
Comparison among E1, SN1, E2, SN2 reaction mechanisms

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