Description: Problems related to aldehydes and ketones: Wittig, imines, acetals, and protecting groups.
Total Problems: 6
Rank the carbonyls A-D below in order of decreasing electrophilicity (reactivity with nucleophiles).
(1 = Most reactive). Explain your reasoning.
Show two ways of preparing the alkene below via the Wittig reaction starting from triphenyl phosphine (PPh3).
Is one route better than the other? Why?
Show what combination of amine and carbonyl would result in each imine or enamine.
When a carbonyl is treated with semicarbazide under acidic conditions an "imine" is produced called a semicarbazone.
Which of the two products below is the correct structure for a semicarbazone? Explain.
Complete each synthesis below. All carbon sources must come from alkenes.
Each synthesis will involve protecting groups.
α-D-glucose is shown below.
a) Is α-D-glucose an acetal, hemiacetal, ketal, or hemiketal?
b) Draw the carbonyl form of α-D-glucose.