Tert-Butyl Chloride Lab Report

When conducting the S_N 1 portion of the experiment, the solvent used was 1% silver nitrate in ethanol solution (〖AgNO〗_3). This solvent is polar protic. This is the best type of solvent needed for an S_N 1 reaction because the hydrogen atom is positively charged while the nucleophile is negatively charged achieving a hydrogen bond. Two factors that contributed to the rate of reaction for S_N 1 are stability of the carbocation and the leaving group departure. The more stable the carbocation, the faster the reaction generates and the better the leaving group, it creates a carbocation faster, which in turn leads to a

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

In order to synthesis tert-butyl chloride, HCl is used in a substitution reaction to displace an OH molecule that is connected to the tert-butyl molecule. Substitution reactions for alkyl halides can go one of two ways; an Sn1 reaction or an Sn2 reaction. An Sn1 reaction is unimolecular (only depends on the substrate), and requires a very weak nucleophile, a polar-protic solvent and favors tertiary alkyl halides as the electrophiles. An Sn2 reaction is the opposite and is bimolecular (depends on the substrate and nucleophile), requires a very strong nucleophile, a polar-aprotic solvents and favors primary alkyl halides as the electrophile. There are a number of factors that can affect the efficiency of these reactions. An Sn2 reaction is affected

SN1 reactions are dependent on the stability of the carbocations, where a tertiary carbocation is at its most stable form, causing a fast reaction rate (Hunt. 2009). The compound that had the highest rate of reaction of less than 1 min was 2-chloro-2-methyl propane, where benzene chloride followed (6 mins). The benzene chloride had a faster reaction than the other haloalkanes since the carbon that was attached to the chloride was connected to the benzene ring, in doing so quickens the reaction. Unlike the benzene chloride, chlorobenzene should have no reaction since the chlorine is directly attached to a carbon within the benzene ring. This unexpected result of having of having the solution turn cloudy may be due to a cross-contamination of the pipettes.

=O bond and cause the chlorine group to leave and a positive charge on the nitrogen. A second ammonia will transfer one of the hydrogens from the positive nitrogen to itself, resulting in a neutral final product. The primary purpose of the experiment is to synthesis

SN1 reactions proceed through a carbocation, the product is a racemic mixture of the substitution product which is a 50/50 racemic mixture. SN2 reactions do not form carbocation, but require the

An E1 reaction involves a two step mechanism. In this particular reaction, before the first step can take place, the alcohol group on 2-methyl-2-butanol is protonated by sulfuric acid so that water is formed as a suitable leaving group. The first step can then take place: the loss of water as leaving group to form a carbocation intermediate. Then, a beta proton is eliminated resulting in the formation of a double bond, forming an alkene. In this reaction, a major product (2-methyl-2-butene) and a minor product (2-methyl-1-butene) are formed.

The alcohol is attacked by a nucleophile; two hydroxyl groups are then formed as intermediates. After a proton shift, one of the alcohol groups is removed and water and etser are

The more stable the resulting carbocation, the quicker this step occurs. After this rate-limiting step, rapid reaction with a weak nucleophile (e.g. ethanol) attacking from either side of the carbocation completes the substitution reaction. A racemic mixture forms with a slight favoring of the inverted molecule because of ion pair formation. A good leaving group capable of delocalizing a negative charge aids in the formation of the initial carbocation. Additionally, polar, protic solvents capable of solvating and stabilizing a carbocation support the SN1 mechanism. Tertiary alkyl halides provide the ideal substrate for the formation of a stable tertiary carbocation that favors the SN1 mechanisms. When testing the factors affecting the SN2 reaction below, the experimenters will achieve the fastest reaction when using a primary alkyl halide with minimal branching and the best leaving group (i.e. 1-bromobutane). Varying the concentrations of the alkyl halide or nucleophile while keeping the other constant will change the rate of reaction for the SN2 reaction. The fastest SN1 reaction will occur for the tertiary alkyl halide with the strongest leaving group reacted in pure

Introduction: The formation of sp2 carbons can be difficult at times because of different reaction environments can cause different outcomes of the product, which generally yields impure products or the wrong products. However, by turning the reagent into a Grignard reagent, it is possible to get a SN2 like reaction to occur most of the time which helps in the formation of certain industrial and pharmaceutical compounds. The Grignard reaction allows sp2 carbons to react with losing its hybridization, and allows carbon chains to be extended while also adding an alcohol functional group, which can be useful as seen when producing selective alcohols. This can be seen in this experiment as the formation of Malachite green, being a dye, or with

This cannot take place on tertiary carbons because triply substituted carbon electrophiles are too crowded for the Sn2 reaction’s backside attack. This method transforms tertiary alcohols into tertiary alkylisonitriles while inverting the stereochemistry. In this method, a special acid catalyst and a nitrogen-containing molecule, a derivative of cyanide is used. The special acid catalyst is scandium (III) trifluoromethansulfate. The acid helps detach a fluorous functional group from one side of the central carbon and then nitrogen forms a new bond on the other side.

The purpose of this lab was to perform a comparison of relative reactivities of various alkyl halides with two different reagents, sodium iodine in acetone and silver nitrate in ethanol. (Below are the reaction equations). We used different substrates, which were primary, secondary, and tertiary. These substrates included 2-bromobutane, 2-bromo-2-methylpropane, 1-bromobutane ∞-Bromotoluene, bromobenzene, and I-bromoadamantane. This lab helped discover what kind of mechanisms (either SN1 or SN2) are involved in the performed reactions.

The synthesis of alkyl halides from alcohol is the basis for this experiment, providing reactions with interesting contrast in mechanisms. Not only synthesizing, but extracting is another important procedure that involves quick actions and judgement, when removing unnecessary layers in a separatory funnel. This allows us to learn and grasp more of an understanding between organic compounds in the laboratory.

Using various alcohols, the substitution reactions (Sn2 and Sn) were utilized by helping with which functional groups reacted, in which way. Developing a mechanism for the alcohols are discussed.

Of the reactions, Reaction II, the addition of a phenyl group to 2’-methylacetophenone, seemed most fitting for Taylor’s labs. Of the two reactions, this reflux seemed better for a lab setting due to its relatively low cost and reflux time. The product too, was much easier to purify and can easily be applicable in an undergraduate lab. Students can vary reactant ratios and the catalyst ratio among labs in order to calculate turnover number and turnover