When tert-butanol is placed in the presence of excess equimolar amounts of chloride and bromide ions...

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Chemistry

When tert-butanol is placed in the presence of excess equimolaramounts of chloride and bromide ions in aqueous acid experimentaldata indicates 45% tert-butyl chloride and 55% tert-butyl bromideis obtained. On the other hand, when n-butanol is placed in thepresence of excess equimolar amounts of chloride and bromide ionsin aqueous acid experimental data indicates 16% of n-butyl chlorideand 84% n-butyl bromide is obtained. Now when n-butanol is placedin the presence of excess equimolar amounts of chloride ions andbromide ions in acid dimethyl sulfoxide the experimental dataprovides an 84% n-butyl chloride and 16% n-butyl bromide as theoutcome.
1.) write balanced chemical equations for all three reactions(hint: account for mole ratios!).
2.) draw complete mechanisms for all three reactions.
3.) calculate the theoretical yield for the chlorides andbromides if each reaction was started with 5.55ml of thecorresponding alcohol, using an aqueous acid media.
Sample: tert
Theoretical g of chloride
Theoretical g of bromide
Sample: n-
Theoretical g of chloride
Theoretical g of bromide
Writing and balancing the equations is what is really throwingme off

Answer & Explanation Solved by verified expert

3.7 Ratings (464 Votes)

The points to be remembera the nucleophilicity of bromide ion in aqueous solution polarprotic solvent is more than the nucleophilicity of chloride ion asthe chloride ion gets more solvatedb the nucleophilicity of bromide ion in DMSO polar aproticsolvent is less than the nucleophilicity of chloride ionso if we are perfoming any reaction in aqeous medium we will getmore of bromo product while in DMSO or DMF we will get more ofchloro productHowever the difference in percentage in first See Answer

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