How are following conversions carried out?
i) 6-hydroxy-6-Methyl- 2-heptanone from 5-bromo-2-propanone using Grignard
reagent
ii) Cyclopentyl methyl ketone from acetoacetic ester
iii) Barbituric acid from molonic ester
iv) Propanol from ethylene oxide
v) Butane from chloromethane
i) 6-Hydroxy-6-Methyl-2-Heptanone from 5-Bromo-2-Propanone using Grignard Reagent:
The conversion involves the use of a Grignard reagent, which is an organomagnesium compound. Here's the mechanism:
1. Synthesis of Grignard Reagent: First, prepare the Grignard reagent by reacting magnesium with 5-bromo-2-propanone. The magnesium replaces the bromine atom, forming a carbon-magnesium bond.
2. Nucleophilic Addition: The Grignard reagent, a strong nucleophile, reacts with a ketone by attacking the carbonyl carbon. In this case, it will react with the carbonyl group in 5-bromo-2-propanone.
3. Work-Up: After the nucleophilic addition, you have a complex mixture. To obtain the desired product, add an acidic work-up (e.g., dilute HCl or H2O) to protonate the oxygen atom in the intermediate. This leads to the formation of 6-hydroxy-6-methyl-2-heptanone.
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Write the mechanism of Paterno-Buechi reaction.
Taking suitable examples explain 1,3-dipolar cyclo-addition reactions.
How would you prepare cis and trans alkene from alkyne? Give its mechanism.
Explain the following:
i) E2 elimination does not give rearranged product.
ii) E1 elimination does not involve isotope effect;
iii) Hofmann elimination gives less substituted alkene
iv) An anti elimination is faster than syn-elimination.
v) The elimination of HCl from chlorofumaric acid is 50 times faster than
chloromalic acid.
Write the full reaction and mark the nucleophile and electrophile in each case.
i) Reaction between potassium cyanide and 1-chloropropane
ii) Reaction between hydrogen bromide and cis 2-butene
iii) Reaction between sodium methoxide and benzyl bromide
iv) Acid catalysed reaction of water with cyclopentene
v) Reaction between ethanal and hydrogen cyanide
Write the product and indicate the type of reaction that is taking place in the following:
Complete following reactions:
