Elimination Reactions of Alkyl Halides
Purpose
The purpose of this lab is to understand the process of eliminating an alkyl halide to form an alkene. The experiment is carried out by first converting the alcohol, 2-methy-2-butanol, into the alkyl halide of 2-chloro-2-methylbutane that will then be put through dehydrohalogenation that favors elimination reaction (E2) to create a mixture of 2-methyl-2-butene and 2-methyl-1-butene. A fractional distillation will be taken to purify the mixture and an additional gas chromatography will be done to further analyze the mixture composition. A bromide test will be done to determine the product of an alkene in the experiment.
Reactions
Reaction 1: Conversion of 2-methyl-2-butanol to 2-chloro-2-methylbutane
In the NaBH4 reduction process, sodium hypochlorite is used as the reagent in order to reduce 4-tert-butylcyclohexanone. The experiment relies on sodium borohydride or NaBH4 iin order for the reduction reaction to take place. NaBH4 is used as the reagent to perform an irreversible reaction of ketones, which is the 4-tert-butylcyclohexanone, attacking
You may have done siinple experiments alkene can be quickly and easily differentiated from an alkane. to learn how an identified, and
The Oxidation of a Secondary Alcohol with Sodium Hypochlorite experiment was performed to show how to change an unknown alcohol into a ketone. The unknown that was found for this experiment was Compound A. Once the ketone was found from the unknown alcohol, an IR and the boiling point was taken to try and figure out what the product and starting alcohol actually is. The first thing that is added to the 1.50 g of unknown compound A is 15 mL of 8.25% of NaOCl, which is a bleach solution. This reacted with the alcohol so the solution could then be tested using the iodide-starch paper. The reaction came out positive when tested because a blue, black spot appeared on the strip.
In the experiment, a color change from purple to brown and the formation of precipitate was observed when butan-1-ol, and butan-2-ol reacted with potassium permanganate. This indicated that a chemical reaction had occurred. A color change, or a precipitate was not observed for 2-methlypropan-2-ol, therefore a chemical reaction had not happened. When all three alcohols reacted with hydrochloric acid, alkyl halides were formed. This was confirmed by the cloudy mixture that was formed because alkyl halides are only slightly soluble in
Main purpose of this lab is to do different tests to identify of an unknown aldehyde or ketone solution.
The purpose of this experiment is to study an electrophilic aromatic substitution. With observing this substitution, the identity of the major product will be discovered. The method used to reach the purpose of the experiment is a TLC. The nitration of methyl benzoate with a mixture of sulfuric acid and nitric acid will be performed in the experiment. NO2 is the electrophile in the experiment, and it is an electron withdrawing group that makes the methyl benzoate less reactive. The NO2 group in this nitration can be added to three different positions —ortho, para, or meta. When the NO2 is added, it makes a methyl nitrobenzoate. The weight recorded of methyl benzoate in the start of the experiment is 3.397 grams. The weight of the crude product
Alkenes are molecules that contain a carbon-carbon double bond and they are hydrated by acid-catalyzed addition of water to that carbon-carbon double bond. This leads to the formation of an alcohol. Two competing processes, hydration and dehydration, establish an equilibrium. The position of the equilibrium is dependent on the condition of the reaction. While hydration of a double bond requires excess water to drive the reaction, dehydration of an alcohol requires the removal of water to complete the reaction. A carbocation is then formed by the addition of a proton to the double bond of norbornene. Steric hindrance determines how the reaction takes place. During such a reaction, the side of the carbocation, formed by the addition
In Part B, the enthalpy change of the neutralization reaction of hydrochloric acid and ammonium hydroxide was determined through 3 sub-reactions. In Reaction 1, hydrochloric acid and sodium hydroxide were reacted in a coffee cup calorimeter. Two Styrofoam cups were stacked together and placed into a 400 mL beaker. 50 mL of 2M HCl solution prepared from Step 1 was measured out using a graduated cylinder and poured into the Styrofoam cup. A lid was placed onto the Styrofoam cup and the temperature probe was inserted through the lid and into the solution.
Alkyl Halides are the common substrate used in substitution and elimination reactions. Alkyl Halides are halogen containing alkane compounds. These compounds are commonly used as the electrophile in substitution reactions. Naming Alkyl Halides is similar to naming alkanes. Halogen substituents are named just like alkane substituents, for example if there is a chlorine attached to an ethane the chlorine substituent will be named using the word chloro-. The other halogens are named using the words flouro-, bromo-, and iodo- respectively. These possible substituents are listed alphabetically along with the alkane substituents.
The objective of the experiment was to prepare a yield of tert-butylchloride through a unimolecular (SN1) nucleophilic substitution reaction.
Haloalkanes on reaction with metals form a special class of compounds – organometallic compounds. Alkyl Halides or R-X reacts with certain metals to produce compounds containing C-metal bonds.
An E1 (unimolecular elimination) reaction is an organic reaction where two groups are removed from the starting molecule in a two-step mechanism. The first group that leaves forms a carbocation intermediate, and the second group that leaves causes the formation of a double bond1. The formation of the carbocation ion in the intermediate is important because that determines the rate of the reaction. If a more stable carbocation can be formed, shifts may occur because the more stable the carbocation intermediate, the faster the reaction can go. Often, two products can result from an E1 reaction; however, it is possible that there is more yield of one product over the other. What makes a product major or minor can be understood with Zaitsev’s rule which states that the product with the most substituted double bond is more stable and will therefore be the major product2. The specific E1 reaction observed in this lab is the acid catalyzed dehydration of 2-methylcyclohexanol. In this case, the first group to leave is an H2O molecule, and the second group to leave is a H+. Two products will result from this reaction- 1-methylcyclohexene and 3-methylcyclohexene. Below in Figure 1 shows the two- step mechanism that occurs.
In day 2 of the experiment in step 1, two millitliters of 2% silver nitrate solution in ethanol were placed insix test tubes. Two drops of the six alkyl halides were added to the test tubes. The alkyl halides included, n-butyl chloride, sec-butyl chloride, t-butyl chloride, n-butyl bromide, allyl chloride, and chlorobenzene. Once the alkyl halides were added, the contents were swirled, and left alone to react. The t-butyl chloride, n-butyl bromide, allyl chloride, and chlorobenzene all reacted and precipitate was formed. It was observed that it took the t-butyl chloride 30 seconds to react and form a precipitate. It was observed that it took the n-butyl bromide four minutes to react, the allyl chloride 1 minute to react, and the chlorobenzene
In order for any elimination reaction to occur, there must be an alkyl halide and a base that will extract a proton. Depending on whether or not the base is strong, will determine which elimination reaction it will undergo. First, the leaving group must be identified. The leaving group is an alkyl halide. The carbon that the alkyl halide is attached to is called the alpha carbon. The next carbon connected to the alpha carbon is the beta carbon. The beta carbon will have beta hydrogens attached to it. The leaving group must first leave. Then the base of the reaction will extract one of the beta hydrogens. When the hydrogen is removed, it leaves the carbon with two valence electrons because of heterolysis. Heterolysis is when both elections from a bond cleavage remain with the bigger, more electronegative atom (Pillai, 26). Since the carbon has two valence
The second part of the lab involves conducting an alcohol dehydrogenase (ADH) assay using a dehydrogenase, an enzyme that catalyzes the removal of hydrogen atoms from a particular molecule. To do this,