Question

In: Chemistry

draw full sn1 mechanism for a reaction that includes 2-methyl-2-propanol, n-pentanol and hydrochloric acid as the...

draw full sn1 mechanism for a reaction that includes 2-methyl-2-propanol, n-pentanol and hydrochloric acid as the reactants and 2-chloro-2-methylbutane and 1-chloropentane as products.

Solutions

Expert Solution

SN1 reactions are nucleophilic substitution reaction with first order kinetics in regard to the organic substrate.

                                                                        HCl

CH3- C(CH3)OH-CH3 +CH3-CH2-CH2-CH2-CH2-OH CH3-CH2-C(CH3)Cl-CH3 +CH3-CH2-CH2-CH2-CH2-Cl

SN1 Mechanism is as follows:

                                                                              

CH3- C(CH3)OH2+-CH3 + CH3-CH2-CH2-CH2-CH2-OH2+ CH3- C+(CH3)-CH3 + CH3-CH2-CH2-CH2-C+H2

CH3-CH2-C(CH3)Cl-CH3 + CH3-CH2-CH2-CH2-CH2-Cl + H2O

Description:

In the 1st step the lone pair of O atom will form bond with H atom as it is positively charged as aresult the carbon attain positive charge. Now the chlorine which has -VE charge will come and donate the electron to carbon to form bond.


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