Interpretation:
Synthetic intermediates A and B have to be drawn.
Concept Introduction:
Conversion of alcohol into
Conversion of primary and secondary alcohols to Chloroalkane is thionyl chloride. The reaction is carried out in the presence of base such as pyridine or trimethylamine.
The reaction of an alcohol with thionyl chloride is the formation of an alkyl Chlorosulfite that converts hydroxide ion (poor leaving group) into Chlorosulfite (good leaving group). Nucleophilic displacement of this leaving group gives product.
Leaving group: Leaving group can be any groups or atoms that get detached from either neutral or charged organic compounds. The stability of the leaving group is to stabilize the electron density that results from heterolysis cleavage of bond.
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Chapter 10 Solutions
Organic Chemistry
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- Compound A of molecular formula C8H14 is reduced by sodium in liquid ammonia to give compound B of molecular formula C8H16. product (Y).Both A and B undergo hydrogenation in the presence of a platinum catalyst to give 2,5-dimethylhexane. Ozonolysis of B with an oxidative workup produces a carboxylic acid of molecular formula C4H8O2. Reaction of B with a peroxyacid gives a chiral C8H14O product, but reaction with bromine gives an achiral C8H14Br2 product. What are the identities of A and B?arrow_forwardDraw the structural formula of the products formed when each alkene is treated with one equivalent of NBS in CH2Cl2 in the presence of light.arrow_forward
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