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De Guzman BSChE-IV
Abstract
I. INTRODUCTION
Organic synthesis is a special branch of chemical synthesis and it and is concerned with the
intentional construction of organic compounds. Organic molecule are often more complex than organic
compounds and their synthesis has developed in one into one of the most important branches of organic
chemistry there are several main areas of research. 1-Bromobutane is a chemical with a formula of
C4H9Br. Colorless transparent liquid in soluble in water slightly soluble in carbon tetrachloride soluble in
chloroform make soluble in ethanol either acetone. It can be used as a chelation agent solvent rare
element extraction agent for organic synthesis.
1-bromobutane is a primary alkyl halide (primary alkyl) and therefore it is produced from
bimolecular nucleophilic substitution reactions (Sn2). Figure 1 shows the reaction for the synthesis of 1-
bromobutane.
+ NaBr + H2SO4 → +
NaHSO4 + H2O
This halide is easily prepared by reacting butan-1-ol (primary alcohol) with sodium bromide
solution and excess of concentrated sulfuric acid. The reaction between sodium bromide and sulphuric
acid was originated in hydrobromic acid (Equation 1).
The use of excess of sulphuric acid allows to increase the degree of completion of the reaction.
Also, the presence of a strong acid like sulphuric acid protonates the butan-1-ol, transforming the
hydroxyl group (-OH) in a better leaving group, the water (H2O). The bromide ion from the hydrobromic
acid reacts as nucleophile, occurring a substitution reaction. The mechanism of the reaction of the
synthesis of 1-bromobutane is shown in Figure 2.
Figure 2. Mechanism of the reaction of the formation of 1-bromobutane
The synthesis performed presents a complex experimental procedure, with several steps. After
the mixture of the stoichiometric reagents, a reflux followed by a simple distillation are carried out, where
some unwanted products can be separated such as, for example, sodium hydrogen sulphate and sulphuric
acid. The liquid collected in the distillation is then washed with water, sulphuric acid and sodium
hydroxide by liquid-liquid extraction to be isolated from other substances (but-1-ene, dibutyl ether and
butan-1-ol that did not react). Finally, the product is dried with anhydrous calcium chloride and purified
by simple distillation.
II. EXPERIMENTAL
Materials:
Procedure:
Filtration Technique under the reduce pressure
The reduce pressure is normally provided by the vacuum container.
It is use of a special valve is attached to the top so the running water can create a soft vacuum.
The liquid is being pulled through and leaving the solid behind.
The filtrate is discarded and you will have a solid ready to go in the purified this is called the
filtration under the reduced pressure.
If no more filtrate coming through.
The pump will switch off
The vacuum can be released.
The scrape the solid in the filter paper and purify it.
10 g of sodium bromide, 10 cm³ of water and 6 g of butanol were place in the round bottom flask
fitted with the reflux condenser.
18 grams of concentrated sulfuric acid were then slowly added over a period of 10 minutes with a
flat standing in the cold water bath.
After which the mixture was gentle boiled under the reflux condenser for 45 minutes.
The apparatus was cold and rearranged the distillation with the condenser in a sloping position.
Distillation was carried out until no more oily drops droplets were collected.
The distillate comprised the two liquid layers which were separated in separating funnel.
The upper aqueous layer was discarded and the lower organic one was returned to the separating
funnel, where the shaken with 10 cm³ of concentrated hydrochloric acid.
After separation, the lower layer was again return to the funnel, where it was shaken with aqueous
sodium hydrogencarbonate.
The organic layer was then run into a small conical flask and allowed to stand over anhydrous
sodium sulphate until it became clear.
Finally the 1-bromobutane was decanted from the sodium sulphate into a small distillation flask
and purified by distillation.
V. THEORIES
Synthetic strategy
The heart of organic synthesis is designing synthetic routes to a molecule. The simplest synthesis
of a molecule is one in which the target molecule can be obtained by using a readily available starting
material for a single reaction that converts it to the desired target molecule. However, in most cases the
synthesis is not that straightforward. To convert a chosen starting material to the target molecule,
numerous steps that add, change, or remove functional groups, and steps that build up the carbon atom
framework of the target molecule may need to be done.
A systematic approach for designing a synthetic route to a molecule is to subject the target
molecule to an intellectual exercise called a retrosynthetic analysis. This involves an assessment of each
functional group in the target molecule and the overall carbon atom framework in it; a determination of
what known reactions from each of those functional groups or that build up the necessary carbon
framework as a product; and a determination of what starting materials (synthetic precursors or synthetic
intermediates) for each such reaction are required. The resulting starting materials are then subjected to
the same retrosynthetic analysis, thus working backward from the target molecule until starting materials
that are commercially available (or available by synthesis following an already published procedure) are
derived.
The retrosynthetic analysis of a target molecule usually results in more than one possible
synthetic route. It is therefore necessary to critically assess each derived route in order to choose the
single route that is most feasible (most likely to proceed as written, with as few unwanted side reactions
as possible) and most economical (involving the fewest steps and using the least expensive starting
materials). The safety of each possible synthetic route (the toxicity and reactivity hazards associated with
the reactions involved) is also considered when assessing alternative synthetic routes to a molecule.
Stereoselectivity
Chemoselectivity
This term refers to the ability of a reagent to react selectively with one functional group in the
presence of another similar functional group. An example of a chemoselective reagent is a reducing agent
that can reduce an aldehyde and not a ketone. In cases where chemoselectivity cannot be achieved, the
functional group that should be prevented from participating in the reaction can be protected by
converting it to a derivative that is unreactive to the reagent involved. The usual strategy employed to
allow for such selective differentiation of the same or similar groups is to convert each group to a masked
(protected) form which is not reactive but which can be unmasked (deprotected) to yield the group when
necessary.
Synthetic reactions
A large variety of organic reactions that can be used in syntheses are known. They can be
categorized according to whether they feature a functional group interconversion or a carbon-carbon bond
formation.
Functional group interconversions are reactions that change one functional group into another
functional group. A functional group is a nonhydrogen, non-all-singly-bonded carbon atom, or group of
atoms. Included in functional group interconversions are nucleophilic substitution reactions, electrophilic
additions, oxidations, and reductions.
Total synthesis
Total synthesis is the laboratory construction of a complex molecule, often a natural product,
through a series of reactions using relatively simple and commercially available molecules as starting
materials. In contrast, semisynthesis starts with larger molecules, also often from naturally occurring
sources, with fewer reactions needed to reach the final product.
In its early days, total synthesis was used as a means of verifying chemical structures. As
analytical chemistry progressed and chemical structures could be determined by instrumental analysis,
researchers moved on to synthesizing complex molecules of biological, medicinal, or material
importance. Today the emphasis in total synthesis is on what is sometimes called “ideal” synthesis: the
efficient production of complex molecular structures in as few steps as possible. Step and atom economy
are green chemistry; they improve synthetic efficiency by increasing yield and reducing waste and time.
However, new reactions are needed to produce large quantities of molecules in a practical and
environmentally friendly way.
The basic steps of total synthesis are isolation, characterization, and a synthetic strategy. First a
compound of interest (target molecule) must be isolated and characterized to determine its structure and
functional properties (such as its pharmacological importance). To develop a synthetic strategy,
investigators do a retrospective (retrosynthetic) analysis, working backward from the target molecule to
identify a series of reactions that would produce it from the available starting materials. In constructing a
retrosynthetic strategy, the analysis must consider the atoms, bonds, functional groups, conformational
properties, and stereocenters of the target molecule.
A classic example of a molecule derived from total synthesis is the monocyclic beta-lactam
antibiotic aztreonam, a structurally modified compound originally isolated from Chromobacterium
violaceum, a gram-negative rod-shaped bacterium. Aztreonam is produced synthetically and is used for
treating infections with gram-negative bacteria.
The limiting reagent in this reaction is 1-butanol. The balanced equation shows that one mol of 1-
bromobutane is obtained for every mol of 1-butanol used. Since we are starting with 2.5 mmoles of 1-
butanol, then the theoretical yield of 1-bromobutane is also 2.5 mmoles, or .342 g.
When determining whether the synthesis was successful or not, the melting point ranges of both
the pure and crude product were obtained and compared to the theoretical given value. This showed that
the purified sample was fairly close to the theoretical value due to the fairly narrow range of the melting
point.
To conclude, the practical techniques were proven to be very effective to raise the value of purity
of the synthesized organic compound. It was successful in providing guidance in the essential
experimental techniques used in any synthesis reaction, separation of products and the impurities, and
purification processes. The expected outcome was realized which is to obtain a reasonably good yield of
product with minimal formation of side products such as alkenes arising from elimination reactions.
It was recommended that when handling very small amounts of substances it is more convenient
to use millimoles (mmoles) instead of moles. We are mainly concerned with reporting the properties of
organic products such as 1-bromobutane, and not inorganic products such as sodium bisulfate. Inorganic
products are typically separated and discarded. Not all reagents are present in equimolar amounts. In such
reactions, the limiting reagent is the one present in the smallest amounts, such as 1-butanol in this
experiment.
References
https://www.coursehero.com/file/12238545/Synthesis-of-Acetaminophen-lab-report/
https://www.coursehero.com/file/p6lsmep/Conclusion-The-purpose-of-this-lab-was-to-perform-an-
organic-synthesis-reaction/
https://chem.libretexts.org/Ancillary_Materials/Laboratory_Experiments/Wet_Lab_Experiments/Organic
_Chemistry_Labs/Lab_II/16%3A_Guidelines_for_Writing_Lab_Reports/16.04%3A_Examples_of_Portio
ns_of_Lab_Reports
Video Reference
https://www.youtube.com/watch?v=0RwDowIgXqk