Formal Lab Report
Name : Rebecce C. Deocampo Date : September 2, 2013
Course/Yr. : BS Chemistry III Sched : MF 7-10, Group#2
Experiment No. 1
Synthesis and Reactivity of Tert-Butyl Chloride
I. Objectives :
1. To produce tert-butyl chloride from tert-butyl alcohol
2. To understand the SN1 and SN2 mechanism involved in the reaction
3. To determine the yield of percentage of t-butyl chloride
II. Introduction
An alkyl halide is a derivative of alkanes. Alkanes are hydrocarbons with a functional group C-C. The hydrogen atom is then replaced by a halogen (F, Cl, Br, I). Therefore, alkyl halides are compounds that have a halogen atom bonded to a saturated, sp3 hybridized carbon atom. These could be classified according to the number of alkyl groups attached to the carbon that is bonded to the halogen atom. A methyl halide does not contain any alkyl group, a primary halide has one alkyl group, a secondary halide has two alkyl groups, and a tertiary halide has three.
Synthesis of alkyl halides can be performed from a variety of starting materials and specific mechanisms: from alkenes by addition, from alkanes by substitution, and from alcohols via nucleophilic substitution. The reaction of alcohols with hydrogen halides, like HCl, HBr, and HI, would result to their corresponding alkyl halides and water. The formation of alkyl halides has different mechanisms, depending on the alcohol used for the synthesis. Tertiary alcohols react with hydrogen halides faster compared to the secondary and primary alcohols. Tertiary alcohols could react with hydrogen halides rapidly at room temperature, while the reaction of primary alcohols with hydrogen halides takes a longer time and should be at a high temperature.
Tertiary alcohols can be converted to their corresponding alkyl chlorides by the addition of concentrated hydrochloric acid to the alcohol. In this experiment, concentrated HCl is added to tert-butyl alcohol to produce tert-butyl chloride via SN1 reaction.
Course/Yr. : BS Chemistry III Sched : MF 7-10, Group#2
Experiment No. 1
Synthesis and Reactivity of Tert-Butyl Chloride
I. Objectives :
1. To produce tert-butyl chloride from tert-butyl alcohol
2. To understand the SN1 and SN2 mechanism involved in the reaction
3. To determine the yield of percentage of t-butyl chloride
II. Introduction
An alkyl halide is a derivative of alkanes. Alkanes are hydrocarbons with a functional group C-C. The hydrogen atom is then replaced by a halogen (F, Cl, Br, I). Therefore, alkyl halides are compounds that have a halogen atom bonded to a saturated, sp3 hybridized carbon atom. These could be classified according to the number of alkyl groups attached to the carbon that is bonded to the halogen atom. A methyl halide does not contain any alkyl group, a primary halide has one alkyl group, a secondary halide has two alkyl groups, and a tertiary halide has three.
Synthesis of alkyl halides can be performed from a variety of starting materials and specific mechanisms: from alkenes by addition, from alkanes by substitution, and from alcohols via nucleophilic substitution. The reaction of alcohols with hydrogen halides, like HCl, HBr, and HI, would result to their corresponding alkyl halides and water. The formation of alkyl halides has different mechanisms, depending on the alcohol used for the synthesis. Tertiary alcohols react with hydrogen halides faster compared to the secondary and primary alcohols. Tertiary alcohols could react with hydrogen halides rapidly at room temperature, while the reaction of primary alcohols with hydrogen halides takes a longer time and should be at a high temperature.
Tertiary alcohols can be converted to their corresponding alkyl chlorides by the addition of concentrated hydrochloric acid to the alcohol. In this experiment, concentrated HCl is added to tert-butyl alcohol to produce tert-butyl chloride via SN1 reaction.
References: [1] Addison, Ault. Techniques and Experiments for Organic Chemistry 4th ed. USA: Allyn and Bacon Inc., 1983. [2] Basic Organic Chemistry Laboratory Manual, Institute of Chemistry, College of Arts and Sciences. University of the Philippines Los Baños. 2004. [3] Organic Chemistry Laboratory Manual. Institute of Chemistry. University of the Philippines Diliman. 2008. [4] McMurry, J. Simanek, E. Fundamentals of Organic Chemistry 5th edition. Thomson Brooks Cole. 2000.