How are following compounds prepared using ethereal solution of diazomethane?
Write the mechanism of the reactions.
i) CH3CH2COOCH3
ii) CH3CH2OCH3
To prepare the following compounds using an ethereal solution of diazomethane, we will employ a process known as diazoalkane synthesis. Diazomethane (CH2N2) is a valuable reagent in organic chemistry for introducing methyl groups into various compounds. It can react with compounds containing acidic protons, like esters and ethers, to form the desired products. Here's the mechanism for each reaction:
i) CH3CH2COOCH3 (Methyl Ethyl Ketone)
Reaction: Diazomethane with Methyl Ethyl Ketone
Mechanism:
1. Generation of Diazomethane: Diazomethane is generated in situ from Diazald, which is a stable precursor. In an ethereal solution, the formation of diazomethane can be catalyzed by a base such as triethylamine (Et3N).
2. Attack on the
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Arrange the following in the increasing order of electrophilic substitution. Justify your answer.
Reaction of primary amine, in presence of an acid, with carbonyl compound
gives an imine. The rate of reaction increases by an increase in acidity but
beyond a certain limit, the rate decreases with further increase of acidity.
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.
In the following pairs which of the carbocation is more stable and why?
i) NC – CH – CH2 +CH2 CH3 or NC - CH2 - +CH2 H2
sec. carbocation p – carbocation
ii) CH3 CH2 +CH - CH2 CH2 CH3 or CH3 (CH2)4 +CH2
sec. carbocation p – carbocation
Write the main product of the following reactions giving reasons for your answer.
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
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