Orgo7 - Organic Chemistry Lab Experiment title Preparation...

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Organic Chemistry Lab Experiment title: Preparation of t-butyl chloride Introduction/Purpose of experiment : The main purpose of this experiment was to prepare t-butyl chloride from t-butyl alcohol and hydrochloric acid by way of an S N 1 reaction. Different reagents such as HX and PX 3 may be used to prepare alkyl halides from primary and secondary alcohols. However, preparing tertiary alkyl halides from tertiary alcohols will only lead to good yields if concentrated hydrogen halides, HX, are used. This is because elimination reactions predominate when tertiary alcohols are treated with phosphorous trihalides. This reaction, commonly known as a nucleophilic alipathic substitution, is the substitution of one group for another at a sp 3 hybridized carbon. The replaced group is commonly known as the leaving group (L), while the group replacing it is known as the nucleophile. The reaction may be considered a Lewis acid-base reaction because the initial carbon attached to the leaving group has Lewis acidic character (electron acceptor); this is due to the electronegative leaving group which polarizes the C-L bond producing a partial positive charge on the carbon atom. Commonly, the exit of the leaving group produces an empty 2p orbital for the nucleophile to occupy and donate its electrons to form a new covalent bond. In this experiment, 2-chloro-2-methylbutane is formed by way of S N 1 (unimolecular) mechanism. Mechanistically, there are two steps in the S N 1 reaction. The first step of the process involves the protonation of the hydroxyl group of the alcohol, which is also known as a Lewis acid-base reaction. Next, ionization occurs in the 2
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Orgo7 - Organic Chemistry Lab Experiment title Preparation...

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