2- Chloro-2-methylpropane chloride

Chloro 2 methylpropane Isobutyl chloride or 2 methylpropyl chloride 2 Chloro 2 methylpropane tert Butyl chloride or 1 1 dimethylethyl chloride... 

Isobutyl chloride (l-chloro-2-methylpropane) [513-36-0] n 1.398. Same methods as described under isoamyl chloride. 

Primary alkyl chlorides are fairly stable to fluorine displacement. When fluorinated, 1-chloropropane is converted to 1-chloroheptafluoropropane and 1-chloto-2-methylbutane produces 39% l-chlorononafluoro-2-methylbutane and 19% perfluoro-2-methylbutane. Secondary and tertiary alkyl chlorides can undergo 1,2-chlorine shifts to afford perfluonnated primary alkyl chlorides 2-Chloro-2-methylpropane gives l-chlorononafluoro-2-methylpropane, and three products are obtained by the fluorination of 3-chloropentane [7] (equation 1). Aerosol fluorina-tion of dichloromethane produces dichlorodifluoromethane which is isolated in 98% purity [4 (equation 2). If the molecule contains only carbon and halogens, the picture is different. Molecular beam analysis has shown that the reaction of fluorine with carbon tetrachlonde, lodotrichloromethane, or bromotrichloromethane proceeds first by abstraction of halogen to form a trichloromethyl radical [5]... 

Chloro-2-methylpropane Water (tert-butyl chloride) (78-88%)... 

The second point to explore involves carbocation stability. 2-Methyl-propene might react with H+ to form a carbocation having three alkyl substituents (a tertiary ion, 3°), or it might react to form a carbocation having one alkyl substituent (a primary ion, 1°). Since the tertiary alkyl chloride, 2-chloro-2-methylpropane, is the only product observed, formation of the tertiary cation is evidently favored over formation of the primary cation. Thermodynamic measurements show that, indeed, the stability of carbocations increases with increasing substitution so that the stability order is tertiary > secondary > primary > methyl. 

Substitutions are very common synthetic reactions by their very nature they produce at least two products, one of which is commonly not wanted. As a simple example 2-chloro-2-methylpropane can be prepared in high yield by simply mixing 2-methylpropan-2-ol with concentrated hydrochloric acid (Scheme 1.10). Here the hydroxyl group on the alcohol is substituted by a chloride group in a facile SnI reaction. Whilst the byproduct in this particular reaction is only water it does reduce the atom economy to 83%. 

Trimethyl phosphite (24.8 g, 0.2 mol) was added dropwise at room temperature to l-isopropoxy-l-chloro-2-methylpropane (30.1 g, 0.2 mol). As heating was begun, methyl chloride began to be evolved. After heating at 100°C for 2 h, the reaction mixture was vacuum distilled. There was thus isolated pure dimethyl 1-isopro-poxy-2-methylpropylphosphonate (27.8 g, 62%) of bp 94 to 95°C/0.8 torr. 

Methylpropane l-Chloro-2-methylpropane (63%) (isobutyl chloride) 2-Chloro-2-methylpropane (37%) (rert-butyl chloride)... 

Experiment 5.49 t-BUTYL CHLORIDE (2-Chloro-2-methylpropane) Me3COH + HC1 -------- Me3CCl + HzO... 

The order of SN2 reactivity is primary > secondary > tertiary, and branching of the chain close to the site of substitution hinders reaction. The unbranched primary halide n-butyl chloride will be the most reactive and the tertiary halide tert-butyl chloride the least. The order of reactivity will therefore be 1-chlorobutane > l-chloro-2-methylpropane > 2-chlorobutane > 2-chloro-2-methylpropane. 

The rate of solvolysis or de-hydrochlorination of /-butyl chloride (2-chloro-2-methylpropane) has been studied very extensively under standardized conditions, and the rate constant has been used as a characterization of solvent polarity. The reaction proceeds according to the scheme ... 

The bromide 3 was prepared by Stuhr-Hansen et al. [10] from the thiol 20 upon treatment with 2-chloro-2-methylpropane in the presence of catalytic amount of aluminum chloride (Scheme 10.6). Lithiation followed by reaction with DMF afforded the aldehyde 7. This aldehyde can be converted to the diethyl phosphonate 8 in three high-yielding steps, via alcohol (21) and bromide (22) intermediates. 

Free energy versus REACTION PROGRESS DIAGRAM FOR THE SN I REACTION OF TERT-BUTYL CHLORIDE (2-CHLORO-2-METHYLPROPANE) AND ACETATE ANION. 

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