(a)
Interpretation: A structure for the alkaloid halosaline, a reason for not getting the product in the given transformation in one step using LAH and a mechanism for the lactone-to-lactam ring contraction have to be found.
Concept Introduction:
Amides on reduction with lithium aluminum hydride followed by water work-up give the corresponding
To find: Draw a structure for the alkaloid halosaline
Get the formation of lithium salt by reduction
(b)
Interpretation: A structure for the alkaloid halosaline, a reason for not getting the product in the given transformation in one step using LAH and a mechanism for the lactone-to-lactam ring contraction have to be found.
Concept Introduction:
If a compound contains both the azide and lactone ring, lithium aluminum hydride reduces both the groups, azide into the corresponding amine and the lactone ring into the
To find: Get the reason for achieving the given transformation in just one step (rather than two) using LAH to reduce both the azide and the amide in one reaction flask
Get the formation of lithium salt by reduction
(c)
Interpretation: A structure for the alkaloid halosaline, a reason for not getting the product in the given transformation in one step using LAH and a mechanism for the lactone-to-lactam ring contraction have to be found.
Concept Introduction:
The simple lactone-to-lactam transformation occurs due to the driving force of amine nucleophiles. A nucleophile is a chemical species that donates an electron pair to an electrophile to form a
To find: Provide a mechanism for the lactone-to-lactam ring contraction
Provide the nucleophilic attack in the starting material
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