BÀI TẬP PHẢN ỨNG THẾ NUCLEOPHILE

Bài 1: For each of the following reactions, assume a concerted process is taking place and draw the
mechanism:

Bài 2: For each of the following reactions, assume a concerted process is taking place and draw the
mechanism:

Bài 3: For the substitution reaction shown below, assume a stepwise process is taking place and draw the
mechanism.

Bài 4: Draw the product for each of the following SN2 reactions:
(a) (S)-2-Chloropentane and NaSH
(b) (R)-3-Iodohexane and NaCl
(c) (R)-2-Bromohexane and sodium hydroxide

Bài 5: When (S)-1-bromo-1-fluoroethane reacts with sodium methoxide, an S N2 reaction takes place in
which the bromine atom is replaced by a methoxy group (OMe). The product of this reaction is (S)-1-
fluoro-1-methoxyethane. How can it be that the starting material and the product both have the S
configuration? Shouldn’t SN2 involve a change in the configuration?Draw the starting material and the
product of inversion, and then explain the anomaly.
Bài 6: Treatment of 5-hexen-1-ol with bromine affords a cyclic product:

The mechanism of this reaction involves several steps, one of which is an intramolecular
SN2-like process:

In this step, a bond is in the process of breaking, while another bond is in the process of forming. Draw
the transition state of this SN2-like process, and identify which bond is being broken
and which bond is being formed. Can you offer an explanation as to why this step is favorable?
Bài 7: Draw the products of the following SN1 reaction:

Bài 7: Draw the mechanism of the following SN1 process:

Bài 8: Draw the mechanism for each of the following SN1 processes:

Bài 9: Treatment of (2R,3R)-3-methyl-2-pentanol with H3O+ affords a

compound with no chirality centers. Predict the product of this reaction and draw the mechanism of its
formation. Use your mechanism to
explain how both chirality centers are destroyed.

Bài 10: Draw the mechanism for each of the following solvolysis reactions:

Bài 11: Does each of the following nucleophiles favor SN2 or SN1?

Bài 12: Determine whether each of the following reactions proceeds via an SN1 or SN2
mechanism and then draw the product(s) of the reaction:

Bài 13: When the following optically active alcohol is treated with HBr, a
racemic mixture of alkyl bromides is obtained:
Draw the mechanism of the reaction, and explain the stereochemical
outcome.
Bài 14: (R)-2-Pentanol racemizes when placed in dilute sulfuric acid.
Draw a mechanism that explains this stereochemical outcome, and
draw an energy diagram of the process.
Bài 15:List the following carbocations in order of increasing stability:

Bài 16: Propose a mechanism for the following transformation:

Bài 17:Determine the number of steps for each reaction and then draw the
mechanism in each case:

Bài 18:Identify the product of the following reaction:

Bài 19:The following reaction is very slow:

(a) Identify the mechanism.

(b) Explain why the reaction is so slow.
(c) When hydroxide is used instead of water, the reaction is very rapid.
Draw the mechanism of this reaction and explain why it is so fast.
Bài 20: Identify the reagents you would use to achieve each of the following transformations:

Bài 21:Propose a mechanism for the following transformation:

Bài 22:When (1R,2R)-2-bromocyclohexanol is treated with a strong

base, an epoxide (cyclic ether) is formed. Suggest a mechanism for formation of the epoxide:

Bài 23:Propose a mechanism for the following transformation: