Identify the mechanism by which the following reactions proceed from. O Na A) +N

Question

Identify the mechanism by which the following reactions proceed from.

O Na A) +NaOH +H2O B) +conc. HBr +H20 OH C) +NaOH +HBrH20 H3 -Aqueous ethanol HO HBr CH3 E) OH SOCI2 pyridine CI +SO2 + BBr3 CH3 BBr3 f= SNI Nucleophilic substitution g S2 Nucleophilic substitution a = Proton transfer d= El Elimination Lewis acidbase e E2 Elimination c Electrophilic addition The rections above involve synthesis or reactions of alcohols and ethers Identify the mechanism by which they proceed from among the mechanisms listed. Use the letters a g for your answers

Explanation / Answer

A) a) proton transfer

Explanation: NaOH is a strong base and abstracts acidic proton to form oxygen anion as product.

B) f) SN1 nucleophilic substitution

Explanation: Reaction of alcohol with HBr gives SN1 mechanism and produces more substituted alkyl halide as product.

C) d) E1 elimination

Explanation: NaOH is a strong base which gives elimination reaction with tertiary alkyl halide and produces alkene as product.

D) f) SN1 nucleophilic substitution

Explanation: Reaction of tertiary alkyl halide with weak nucleophile gives SN1 mechanism and produces racemic mixture of products.

E) g) SN2 nucleophilic substitution

Explanation: Reaction of alcohol with SOCl2 produces alkyl halide. This mechanism follows SN2 mechanism.

F) b) Lewis acid base

Explanation: The electron density on oxygen atom is donated to empty orbital of boron and forms complex.

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