1.5.1
Comparison of Three Isomers of Butanol
Introduction:
An alcohol's reactivity is determined based on the attachment of their hydroxyl functional
group. The location of this hydroxyl functional group will impact the molecular structure of the
alcohol, making it either primary (1° ), secondary (2° ), or tertiary (3° ). If the OH is bonded to only one other carbon, it is a primary alcohol (eg. 1-butanol); if bonded to two other carbons, it is a secondary alcohol (eg. 2-butanol); if bonded to three other carbons, it is a tertiary alcohol (eg. 2-methyl-2-propanol). Due to the placement of the hydroxyl functional group in each of the degrees of alcohol, the reactivity of each should be impacted. This means that all three
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4. Write a structural diagram equation to represent the reaction between each alcohol and HCl(aq).
5. Write a structural diagram equation to represent the controlled oxidation of each alcohol in KMnO4(aq) solution.
6. Summarize in a few sentences the halogenation and controlled oxidation reactions of 1°, 2°, and 3° alcohols. During the halogenation reactions of 1-butanol, 2-butanol, and 2-methyl-2-propanol, there is a formation of water from the OH atom of the alcohol, and the H atom from the HCl solution. The OH bond of the alcohol is then substituted with the Cl atom. Therefore all of the degrees of alcohol undergo halogenation reactions, and form alkyl halides as products. This is because the functional group of alkyl halides is a carbon-halogen bond. A common halogen is chlorine, as used in this experiment.
The products of the primary alcohol reaction, 1-butanol and HCl, are 1-chlorobutane and water; products of the secondary alcohol, 2-butanol and HCl are 2-chlorobutane and water; products of the tertiary alcohol, 2-methyl-2-propanol are 2-methyl-2-chloropropane and water. In the controlled oxidation reactions of 1-butanol and 2-butanol with KMnO4, there is also a formation of water. The primary alcohol 1-butanol, reacted with KMnO4 to create butanal, an aldehyde, and water as products. Also the secondary alcohol, 2-butanol and KMnO4
In an oxidation reaction, the number of C-H bonds decreases or the number of C-O bonds increases, while in a reduction reaction, the number of C-H bonds increases or the number of C-O bonds decreases. In the oxidation step of this reaction, 4-tert-butylcyclohexanone is formed from when a C-H bond is lost while a C-O bond is gained to create a carbonyl. In the reduction step, 4-tert-butylcyclohexanol is formed when the carbonyl is converted into an alcohol when a nucleophilic hydride attacks the carbonyl. Whether the OH is in the
Grignard reagents are reactive enough to also attach esters; however, two equivalents of the Grignard reagent are usually added because less then two equivalents leave a large quantity of unreactive ester. This reaction forms a tertiary alcohol.
In the Cannizaro reaction an aldehyde is simultaneously reduced into its primary alcohol form and also oxidized into it 's carboxylic acid form. The purpose of this experiment is to isolate, purify and identify compounds 1 and 2 which contain 4-chlorobenzaldehyde, methanol, and aqueous potassium hydroxide. Compounds 1 and 2 are purified by crystallization. . The purified product will be characterized by IR spectroscopy and melting point.
Ethanol is another one of the key components that reacts with oxygen according to the equation:
3. State the name and structure of the functional group for each type of biologically
Abstract: Using hypochlorous acid to convert secondary alcohol called cyclododecanol to the corresponding ketone which is cyclododecanone by oxidation.
Introduction: The purpose of this experiment is to understand the kinetics of the hydrolysis of t-butyl chloride.The kinetic order of reaction was studied under the effects of variations in temperature, solvent polarity, and structure. It is particularly observed in tertiarhalides i.e. in SN1mechanism, Nucleophilic Substitution which is in 1storder. It is basically a reaction that involves substitution by a solvent that pretendslikea nucleophile i.e. it donates electrons. The reaction being in firstorder means
Purpose: The purpose of this experiment is to observe a variety of chemical reactions and to identify patterns in the conversion of reactants into products.
The Grignard reaction is an important synthetic process by which a new carbon to carbon bond is formed. Magnesium metal is first reacted with an organic halide forming the Grignard reagent. The Grignard reaction is the addition of an organomagnesium halide (Grignard reagent) to a ketone or aldehyde, to form a tertiary or secondary alcohol, respectively. For example, the reaction with formaldehyde leads to a primary alcohol. Grignard Reagents are also used in the following important reactions: The addition of an excess of a Grignard reagent to an ester or lactone gives a tertiary alcohol in which two alkyl groups are the same, and the addition of a
The purpose of this experiment is to determine the nucleophilic strength of chloride and bromide ions as it reacts with 1-butanol (n-butyl) and 2-methyl-2-propanol (t-butyl alcohol) under SN1 and SN2 conditions.
The products of interest within this experiment are 2-methyl-1-butene and 2-methyl-2-butene from sulfuric acid and phosphoric acid catalyzed dehydration of 2-methyl-2-butanol. The reaction mixture was then separated into its separate alkene components by steam distillation and then analyzed by gas chromatography (GC), Infrared Radiation (IR) spectroscopy, and Nuclear Magnetic Resonance (NMR) imaging. Gas chromatography is an analytical technique that is able to characterize if specific compounds exist in a reaction mixture, even if they are in low quantities, assess how much of a compound exists within a reaction mixture relative to other components within the sample, and determine the purity of an isolated product. In the case of this experiment, gas chromatography is used to analyze how pure the alkene reaction sample was and if any remnants of impurities or 2-methyl-2-butanol remained in the sample after isolation of alkene components.
The reaction took place in a conical vial and .2mL of each of the reactant samples were added to it along with some 95% ethanol. Two drops of NaOH were added shortly after and stirred at room temperature for fifteen minutes. The vial was cooled in and ice bath and crystallized. Vacuum filtration was performed to filter the crude product. The crude product was recrystallized using methanol and filtered again. We made one change to the procedure and instead of using .7mL of ethanol we
The purpose of the experiment is to oxidize a secondary alcohol (2-octanol) by using sodium hypochlorite (bleach) to produce 2-octanone. The starting material consisted of a sample of 2-octanol that was placed into a three-neck flask along with acetic acid and acetone creating an acidic solution. While monitoring temperature fluctuations to ensure a temperature of 400 Celsius was not reached, sodium hypochlorite slowly dripped from a separatory funnel into the acidic solution. Once this reaction reached its entirety, the solution was combined with sodium bisulfate to remove any of the remaining oxidizing agent. This solution was then tested and brought to a neutral pH using a sodium hydroxide solution. The reaction material was extracted using ether and was then washed with a saturated sodium chloride solution. The organic solution was then dried using magnesium sulfate and was then decanted and placed onto the rotovap. The produced weighed .599g and based on the infrared spectrum analysis (see Figure 1) preformed on the product it was determined to be 86.1% 2-octanol, which means .516g of 2-octanol was obtained in the final product.
The oxidation reaction occurs as a two-step reaction. The first step involves the formation of chromate esters and the second step is an elimination reaction that will produce the carbonyl group necessary to make either a ketone or an aldehydes. The reaction is hallmarked by the breaking of a C-H bond and the formation of a C-O bond (James, 2014). Specifically when oxidizing alcohols, it is important to note that primary alcohols can be converted to aldehydes as well as completely to carboxylic acids, secondary alcohols are converted to ketones and no further, and tertiary alcohols cannot be oxidized. The oxidizing agent removes the hydrogen from the –OH group and the hydrogen from the C-H group attached to the –OH group in a compound. Tertiary alcohols cannot be oxidized because they lack the C-H bond that is present in both the oxidation of primary and secondary alcohols (Clark, 2003).
The objective of this experiment is to successfully perform a dehydration of 1-butanol and 2-butanol, also dehydrobromination of 1-bromobutane and 2-bromobutane to form the alkene products 1-butene, trans-2-butene, and cis-2-butene. The dehydration reactions react under and acid-catalysis which follows an E1 mechanism. It was found that dehydration of 1-butanol yielded 3.84% cis-2-butene, 81.83% trans-2-butene, and 14.33% 1-butene, while 2-butanol is unknown due to mechanical issues with the GC machine. For the dehydrobromination, with the addition of a