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Nucleophilic Substitution

This document discusses nucleophilic substitution reactions of types SN1 and SN2. The SN1 reaction involves the formation of a carbocation intermediate and proceeds through a single, rate-determining step. Factors that stabilize carbocations such as tertiary carbocations and protic solvents increase the rate. The SN2 reaction proceeds through a single, concerted step involving a pentacoordinate transition state. Steric hindrance of substituents near the reaction center decreases the rate. Polar, aprotic solvents increase the rate by stabilizing transition states and reactive intermediates. An experiment is described to observe the effects of alkyl chain structure, leaving groups, and temperature on the relative rates of SN1 and SN2 reactions

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Jansen B. Lauren
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18 views9 pages

Nucleophilic Substitution

This document discusses nucleophilic substitution reactions of types SN1 and SN2. The SN1 reaction involves the formation of a carbocation intermediate and proceeds through a single, rate-determining step. Factors that stabilize carbocations such as tertiary carbocations and protic solvents increase the rate. The SN2 reaction proceeds through a single, concerted step involving a pentacoordinate transition state. Steric hindrance of substituents near the reaction center decreases the rate. Polar, aprotic solvents increase the rate by stabilizing transition states and reactive intermediates. An experiment is described to observe the effects of alkyl chain structure, leaving groups, and temperature on the relative rates of SN1 and SN2 reactions

Uploaded by

Jansen B. Lauren
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© Attribution Non-Commercial (BY-NC)
We take content rights seriously. If you suspect this is your content, claim it here.
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Nucleophilic Substitution

Nucleophilic Substitutions (SN1, SN2) of Halides

The Unimolecular (SN1) Reaction: 2 steps


(1)

R-X dissociates, forming a carbocation intermediate, R+, and the leaving group, X-.

(2)

Slow step = rate determining step (r.d.s.). Entails only one species, R-X.

Nu

R-Nu

Carbocation and nucleophile combine. Fast step. Overall reaction: R-X + Nu- R-Nu + X-.

Rate of the reaction = k[R-X]

SN1 Reaction
R R R
R R R C Nu + Nu C R R R

rate determining s tep C X R

R C+ R

Nu

Carbocation stability is important factor: 3 > 2> 1. Polar, protic solvents such as ethanol support carbocation formation (stabilize intermediate). Aprotic solvents such as acetone do NOT support carbocation formation. Weak nucleophile is OK.

The Bimolecular (SN2) Reaction: 1 step


(1)

Nu

R-X

+ Nu

Nucleophile combines with alkyl halide to form pentacoordinate transition state.

Slow step = rate determining step (r.d.s.). Entails two species, R-X and Nu-.

(2)

+ Nu

Nu-R

Transition state dissociates to form product, Nu-R, and halide ion, X-.

Rate of the reaction = k[R-X][Nu-]

SN2 reaction
H H H X H Nu

Nu :

H H

Nu H

C
H

Steric factors are important: 1 > 2 > 3. Polar, aprotic solvents such as acetone increase rate of SN2. Aprotic solvent destabilizes nucleophile (increases its reactivity). Strong nucleophile is necessary.

The nature of the leaving group is important in both SN1 and SN2 reactions: I > Br > Cl.

Experiment: Structural Effects (Part A only)


Possible Products 0.2 mL (4 drops) Possible Products
I

OEt

Cl

OEt
2 mL 95% EtOH AgNO3

Br
2 mL NaI acetone

+ AgCl OEt

+ NaCl I

Cl

SN1
OEt
Cl
Br

SN2
I

OEt

Experiment
You will have 2 series of 5 test tubes with 0.2 mL (4 drops) of each reactant. You will monitor time for cloudiness. If NaI/acetones do not react after 30 min, heat to 50 C in water bath (loose corks!!!) If 95% EtOH/AgNO3 tubes do not react after 30 min, also heat to 50 C. Students must include statements in their lab reports about the following: 1. 2. 3. 4. 5. Alkyl halide structure (1, 2, 3) and SN2 Alkyl halide structure (1, 2, 3) and SN1 The leaving group (Br vs. Cl) Aryl halide reactivity Temperature and rate All statements must be based on observations. Grading: 50% on the written report and 50% on observations, results, discussion and conclusions.

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