MSDS SHEETS

ÇUKUROVA UNIVERSIY
SCIENCE AND LITERATURE FACULTY
CHEMISTRY DEPARTMENT.
ORGANIC CHEMISTRY LABORATORY I.

synthetisation of butyl bromide using N-butyl alcohol

as a reactant or starting product

Daniel Alejandro Malaver Rangel.

2019144315

ADANA, DECEMBER 2022

INDEX
1. objective of the experiment.

2. Theoretical information.

3. Experiment Procedure and main scheme.

4. Mechanism.

5. General observations.

6. Results and comments.

7. Sources.

8. MSDS.
  Objective of the experiment.:
to synthesise butyl bromide under SN2 conditions.

 Theoretical information
During the synthetisation of butyl bromide, the mechanism that will take place is a Sn2
mechanism. The main reason of this is the fact that the main reactant, which is butyl alcohol,
has the hydroxyl group at the end of the carbo chain making it a primer alcohol. Theses alcohol
Substitution reaction normally happens under Sn2 conditions; these conditions are: the presence
of a Hydronium source, the presence of a strong nucleophile and, by last, a source of energy.
The SN2 reaction (also known as bimolecular nucleophilic substitution or forward attack) is a
type of nucleophilic substitution, where a lone pair of electrons from a nucleophile attacks an
electrophilic centre and binds to it, driving out another group called the leaving group.
Consequently, the entering group replaces the leaving group in one stage. Since both reacting
species are involved in this slow rate-limiting step of the chemical reaction, this leads to the
name bimolecular nucleophilic substitution, or SN2. Among inorganic chemists, the SN2
reaction is often known as the exchange mechanism.

Factors that affect the Sn2 Reaction

 The basicity of the leaving group: By comparing the SN2 reaction rate of compounds
with atoms in the same periodic group (for example, the halides), the results show that
the ability as a leaving group during an SN2 reaction depends on its basicity. In general,
the lower the basicity of a group, the greater its ability as a leaving group.
 The size of the nucleophile. How easily a compound attacks an electron deficient atom
also affects an SN2 reaction. As a rule, negatively charged species (eg OH -) are better
nucleophiles than neutral species (eg H2O, water). There is a direct relationship between
basicity and nucleophilicity: stronger bases are better nucleophiles.
 Solvent. If a reaction is carried out in a protic solvent, whose molecules have a hydrogen
atom bonded to oxygen or nitrogen, the larger atom is a better nucleophile in an SN2
reaction. In other words, the weakest base is the best nucleophile in a protic solvent.
 steric effects. Steric hindrance is any effect of a compound, due to the size or position
of substituent groups. Steric effects affect nucleophilicity, but do not affect the strength
of the base. A bulky nucleophile, such as the tert-butoxide ion with its specific
arrangement of methyl groups, is a poorer nucleophile than the ethoxide ion, with a
straight carbon chain, even though tert-butoxide is a stronger base.
 Experiment procurement

 Mechanisms related to the experiment

  General observations

 During the experiment a small yellow oil-alike face was

observed.
 The concentrated sulphuric acid released a lot of heat at the
moment of being mixed with the solution releasing a white
smog.
 Drops were seen in the condensation tube as a sing of a
compound that was in the solutıon was reaching its boiling
point
 All the samples were taken by the controlling personal and
poured inside of a communal beaker, at the bottom of it there
was a crystalized compound
 In the bottom of the communal beaker a liquid face was seen
 In the surface of the communal disposal beaker a yellow
organic face was appreciated.

 Discussion and result analysis

It is important starting by saying that the organic face of the balloon was a really small
yellowish line showing that the presence of butyl bromide was quite small compared to the
waterish face, the explanation of the low yield might be:
1. The reaction was stopped and suspended in a short period, as we know, a Sn2 reaction
might take some time to take place due to energetically speaking is endothermic. Some
reactions might even take weeks to be completed. However, during the practice the
reaction was just left for around one and a half hour
2. A lot of energy was applied in the reaction and instead of butyl bromide, butene was
produced. The heater was left at 250 at the beginning by mistake. This might have
avoided the formation of butyl bromide allowing the alcohol to be dehydrated. Butene
is known for being a colorless liquid with a colorless gass
One more factor to be taken into account is the crystal that was formed in the bottom of the
disposal beaker that was used for collecting the samples used and created during the practice or
experiment. This crystal is the clear sıgnal that the reaction did not happen and indeed sodium
bromıde precipitated back again being a low soluble compound in butanol(1-butanol:
0.246g/100ml(25°C)).
The role that played the different spieces in the reaction are the following
 Sulfuric acid was added as a source of hydronıums ions in oder to create butyloxonium
ions
 Sodium bromide was the source of our nucleophilic agent
 Water helped the bromur-sodyum dissociation
Despite of not having been able to produce properly butyl bromure, the process followed was
successful as it was followed in the required conditions. besides of this, it is important to remark
the educational porpoise of it was reached and fulfilled completely.

 Sources

Erdik, ender, Yüsekşık, nadire, Öktemer, atilla, & Pekel, tarik. (2011). organik kimyasal
analisis. In metin Obalı (Ed.), Denel organik Kimya (7 baskı, pp. 962–965). essay, gazi
kitapevi.

Giuliano, R. M. (2016). Organic Chemistry. Mcgraw-hill Education - Europe.

SN2: Cinética, Mecanismo Y Estereoquímica. Mecanismo SN2. (n.d.). Retrieved December 3,

2022, from http://www.qorganica.es/qot/T3/sn2_mecanismo_exported/index.html
 Mechanisms related to the experiment