Concept explainers
Interpretation: The reason behind loss of optical activity of
Concept introduction: Haloalkane solvolysis is a typical example of unimolecuar substitution. It proceeds via two-step mechanism. The first slow step that determines rate is the removal of leaving group from the substrate haloalkane and generates a carbocation. Since the rate is only governed by substrate alone and no other nucleophile or solvent it is termed as unimolecuar substitution. The final step is attack of nucleophile on carbocation generated and formation of racemic products. The most important outcome of unimolecuar substitution is conversion of an optically active substrate to racemic mixture of products.
Tertiary or secondary halides undergo fastest unimolecuar substitution as they can readily form the tertiary carbocation followed by secondary and least reactive are primary.
The
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Organic Chemistry: Structure and Function
- 4. Synthesis Using the carbon-containing starting material(s), propose a synthesis by drawing structures for all intermediates. The carbon atoms in the product must originate from the starting material(s) (or a carbene/carbenoid or CO₂), but you may use as many equivalents of each starting material as you would like, and any reagent/reaction you know. (note: no mechanisms are required). (a) || محمد barrow_forward(d) Consider the following catalyzed and non-catalyzed pathways of a substitution reaction of bromoethane. Draw an energy diagram for each of the following reactions (label all axes and include reactants, intermediates (if any) and products). CH3CH₂Br + HO CH³CH₂OH + B (non-catalyzed) ное CH3CH₂Br + CH3CH₂OH + 1 (catalyzed) CH3CH₂ + Brarrow_forward2) Provide a detailed mechanism for the addition reaction shown below. State the regiochemistry and explain why it's unusual. Please be sure to include all structures (use line angle notation or perspective diagrams as appropriate to illustrate the stereochemistry of the process), resonance forms, intermkediates, transition states, curved arrows, formal charges, or lone pairs as necessary. Please don't cheat. Br HBr SCH3 SCH + ENarrow_forward
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