Substitutions, Eliminations & Reactions yielding Alkyl Halides
Using the drawing pallet on the right, draw the structure
of the major organic product for the reaction shown below:
PBr3 reacts with alcohols to give alkyl bromides. The reaction involves an intermediate phosphite ester and proceeds with inversion of stereochemistry, although there is no stereocenter involved in this reaction.
Using the drawing pallet on the right, draw the structure
of the major organic product for the reaction shown below:
The tertiary tosylate will decompose in the polar solvent to give the tertiary carbocation. There will be competing reaction from the solvent, to give the ethyl ether, and the more nucleophilic amine, to give the secondary amine.
Using the drawing pallet on the right, draw the structure
of the major organic product for the reaction shown below:
SOCl2 in a non-polar solvent reacts with alcohols by first forming a sulfite ester, which undergoes an SNi mechanism which proceeds with frontside attack and retention of stereochemistry.
Using the drawing pallet on the right, draw the structure
of the major organic product for the reaction shown below:
NBS in CCl4 results in allylic bromination. There are three allylic positions in this molecule, and a mixture of products will be observed; the least hindered methylene on the side-chain is shown as the answer.
Using the drawing pallet on the right, draw the structure
of the major organic product for the reaction shown below:
Acetate anion, a weak base, will react with the secondary tosylate by an SN2 mechanism to give the acetate ester.
Using the drawing pallet on the right, draw the structure
of the major organic product for the reaction shown below:
PBr3 reacts with alcohols to give alkyl bromides. The reaction involves an intermediate phosphite ester and proceeds with inversion of stereochemistry. In this reaction, the bromine and one of the methyl groups are equatorial in the final product.
Using the drawing pallet on the right, draw the structure
of the major organic product for the reaction shown below:
HBr in the presence of peroxides generates bromine radical, which adds to an alkene to give an anti-Markovnikov alkyl bromide. Remember that the driving force for the regiochemistry is the formation of the most stable radical intermediate.
Using the drawing pallet on the right, draw the structure
of the major organic product for the reaction shown below:
NBS in CCl4 results in allylic bromination. There is only one allylic position in this molecule, giving the product shown.
Using the drawing pallet on the right, draw the structure
of the major organic product for the reaction shown below:
SOCl2 in a polar solvent (pyridine) reacts with alcohols by first forming a sulfite ester, which undergoes an SN2 substitution proceeding with inversion of stereochemistry.
Using the drawing pallet on the right, draw the structure
of the major organic product for the reaction shown below.
Dehydration of an alcohol (an elimination reaction) proceeds by a stepwise mechanism involving a carbocation intermediate. Rearrangements are common and this reaction involves the intermediate formation of a tertiary carbocation, which then undergoes loss of a proton to give the alkene.
That is correct!
Sorry, that is not correct. You should modify your
structures and try again. If cis-trans-
stereochemistry is required, please make sure you have
drawn the appropriate isomer using the "wedge bonds".
Note: Stereochemistry is shown
using the "wedge" bond.
Click on the solid wedge to reverse
orientation.
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