Chapter 17: Q11P (page 543)
Use the reaction of a Grignard reagent with a carbonyl compound to synthesize the following compound:
Short Answer
The reaction of cyclohexanone with Grignard reagent is shown as,
Chapter 17: Q11P (page 543)
Use the reaction of a Grignard reagent with a carbonyl compound to synthesize the following compound:
The reaction of cyclohexanone with Grignard reagent is shown as,
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Get started for freePropose a synthesis of bicyclohexylidene, starting from cyclohexanone as the only source of carbon.
A compound of unknown structure gave the following spectroscopic data:
Mass spectrum:
IR:
NMR: 1.4 (2H, quartet, J=7Hz); 1.2 (6H, singlet); 1.0 (1H, singlet); 0.9 (3H, triplet, J=7Hz)
NMR: 74, 35, 27, 25
(a) Assuming that the compound contains C and H but may or may not contain O, give three possible molecular formulas.
(b) How many protons (H) does the compound contain?
(c) What functional group(s) does the compound contain?
(d) How many carbons does the compound contain?
(e) What is the molecular formula of the compound?
(f) What is the structure of the compound?
(g) Assign peaks in the moleculeโs NMR spectrum corresponding to specific protons.
The reduction of carbonyl compounds by reaction with hydride reagents and the Grignard addition by reaction with organomagnesium halides are examples of nucleophilic carbonyl addition reactions. What analogous product do you think might result from reaction of cyanide ion with a ketone?
Question:For each reaction, write the mechanism using curved arrows for the conversion of the alcohol into the corresponding alkene with POCl3. In each case, explain the regiochemistry of the elimination.
a)
b)
c)
Give IUPAC names for the following compounds:
(a)
(b)
(c)
(d)
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