University of Manitoba

CHEM 2210 - Introductory Organic Chemistry 1

Laboratory Report 3: Substitution Chemistry

Student: Ygor Dantas Furtado

Lab Section: B06, Room #: 290

October 8, 2015

1. For the experiment of Day 1 and 2:

a. Rationalize using theory whether the reactions are likely to
undergo a Sn1 or Sn2 mechanism.
-

The reaction to make the tert-butyl chloride would undergo

Sn1 mechanism. Due to the fact that were using a protic
Solvent (H2O) from the HCl concentrated solution. Also,
tertiary Carbons are more likely to undergo Sn1
mechanism due to the high stability of the carbon cation
and also its high reactivity. In addition, we also have a very
good leaving group (OH).Moreover, we also used a weak
Nucleophile Cl-. So, we have all the pre-requisites to
confirm that the reaction to make the tert-butyl chloride
undergo Sn1 mechanism.

The reaction to make the 2-butoxynaphthalene would

undergo Sn2 mechanism. The explanation for that is a little
bit more complex. For this reaction with have that the rate
will depend on the [2-Naphtol] and [Iodobutane]. The NaOH
will be responsible to deprotonate the 2-Napthol to react
further with the Iodobutane. This is not a general Sn2
reaction since we used a protic solvent (EtOH).

The first intermediate is

and the second is

b. Draw the reaction profile diagrams for both reactions.

Sn1 Mechanism Energy Diagram

Sn2 Mechanism Energy Diagram

2. For the synthesis of 2-butoxynaphthalene:

a. Why was the NaOH necessary?
-

The NaOH was necessary to deprotonate the 2-Naphtol to

make it a better nucleophile.

b. What other substitution product could there be?

-

Butanol

c. What are four ways to speed up this reaction? Be sure to

describe how these act to speed up the reaction.
-

Increasing the [2-Naphtol], rate = k[2-Naphtol][Iodobutane]

Increasing the
[Iodobutane]

[Iodobutane],

rate

k[2-Naphtol]

Increase the temperature. Increasing the temperature

increases the frequency in which molecules collide with
each other. So, high temperatures mean higher rates.

3. Do you think tert-butyl chloride will react with water? If so, show the
mechanism of the reaction and expected product.
-

Yes, it would react with water in acid condition to form an

alcohol.

4. Should a percent yield or percent recovery be reported for these

reactions? Show your work on how that number is calculated for both
experiments.
-

Percent yield must be used since were talking about

efficiency of a reaction.

For 2-butoxynaphthalene
yield=

amount of product that we actually got

amount of product expected (Theoretical)

yield=

0.17 g
x 100=25.50
0.667 g

Calculating the amount of product expected:

For tert-butyl chloride

yield=

amount of product that we actually got

amount of product expected (Theoretical)

yield=

3.83 g
x 100=64.70
5.92 g

Calculating the amount of product expected:

5. Using all possible evidence, describe the purity of the products (2butoxynapthalene and tert-butyl chloride)
For 2-butoxynaphthalene
The purity was assigned by TLC, melting point and IR techniques. The
TLC plate showed that we still have some of the start materials. We got
3 different signals on the product spot. One of these signals represents

the 2-naphtol (Rf= 0.44). We can check that when we compare with
the signal of just the start material (Rf= 0.44). Then we know that
there are more 2 compounds in our product. One of those 2 must be
the iodobutane and the other one must be our desired product.

The IR showed that we got our product.

IR data
Peak (cm-1)

Functional
group

3057/2956/2868

C-H

1627

C=C
(aromatic)

About 1200

C-O

We did not see a broad peak about 3300 that would represent the (OH)
group from the 2 naphtol so our product may not contain start material
anymore. This difference in results can be due to the fact that the TLC
was analyzed using the reaction mixture while for the IR we just used
the precipitated material. However, the melting point analysis

confirmed that the product was not pure. The melting point observed
was 32 0C while in the literature it must be between 35 to 36 0C1.
For tert-butyl chloride

The purity was assigned via IR spectroscopy. No braod peak about 3300 that
would represent the OH bond from the tert-butanol. We have a peak at 567
cm-1 that represents
C-Cl. So we can conclude that we made the tert-butyl chloride. Another think
that we can analyze is the aspect of our solution. The solution was colorless
and transparent, which indicate that there was not water present.
6. Attach your IR spectra for both products

1 Chem Spider Web site: http://www.chemspider.com/Chemical-Structure.74597.html

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