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Chapter 4: Problem 92

Methyl ethanoate \(\frac{\text { (i) } \mathrm{CH}_{3} \mathrm{MgCl}(\text { excess })}{\text { (ii)Hydrolysis }} \mathrm{x}\). The product \(\mathrm{x}\) in the above reaction is

Short Answer

Expert verified
Answer: The final product 'x' is tert-butanol (\(\mathrm{CH}_{3} \mathrm{C}(\mathrm{CH}_{3})_{2} \mathrm{OH}\)).

Step by step solution

01

Identify the functional group in the starting compound.

Methyl ethanoate is an ester (\(\mathrm{CH}_{3}\mathrm{COOCH}_{3}\)) which has the general formula \(\mathrm{R-COO-R'}\). In this case, both R and R' are methyl groups (CH₃).
02

Understand the reactivity of Grignard reagents with esters

Grignard reagents (\(\mathrm{RMgX}\)) are strong nucleophiles that can react with electrophiles like carbonyls. In this case, the ester (Methyl ethanoate) has a carbonyl group that will react with Grignard reagent (\(\mathrm{CH}_{3} \mathrm{MgCl}\)).
03

Perform the first reaction - Grignard reagent with Methyl ethanoate

Treat Methyl ethanoate with an excess of Grignard reagent, which will result in a nucleophilic attack on the carbonyl carbon. This reaction will lead to the formation of a ketone after the initial O-alkylation and substitution, and further nucleophilic attack by Grignard reagent because the reaction is carried out in excess which ultimately forms tertiary alcohol. The intermediate product would be \(\mathrm{CH}_{3} \mathrm{C}(\mathrm{CH}_{3})_{2} \mathrm{OH}\) (tert-butanol).
04

Perform the second reaction - Hydrolysis

Hydrolysis is the reaction between a compound and water, resulting in the breaking of a bond in the compound and the formation of two new products. In our case, since tert-butanol isn't subject to hydrolysis, there will be no change in the product.
05

Determine the final product

After going through Grignard reaction and hydrolysis, the final product 'x' is \(\mathrm{CH}_{3} \mathrm{C}(\mathrm{CH}_{3})_{2} \mathrm{OH}\) (tert-butanol).

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Most popular questions from this chapter

The compound which gives yellow precipitate when heated with iodine and alkali is (a) propan - 1 -ol (b) methanol (c) tert-butyl alcohol (d) butan- \(2-\) ol

The products formed in the above reaction are (a) \(\mathrm{CH}_{3}-\mathrm{CHO}, \mathrm{HCHO}, \mathrm{HCOOH}\) (b) \(\mathrm{CH}_{3}-\mathrm{CHO}, \mathrm{HCOOH}\) (c) \(\mathrm{CH}_{3}-\mathrm{CHO}, \mathrm{OHC}-\mathrm{CHO}\) (d) \(\mathrm{CH}_{3}-\mathrm{COOH}, \mathrm{HCOOH}\)

What is the product of addition of \(\mathrm{HCl}\) to \(\mathrm{CCl}_{3}-\mathrm{CH}=\mathrm{CH}_{2} ?\)

Identify the false statement among the following (a) The rate of hydrolysis of tert-butyl chloride does not change by increasing the concentration of \(\mathrm{OH}^{-}\). (b) 1 -phenylethanol reacts with thionyl chloride to give a chloro compound with almost complete retention of configuration. (c) Polar solvents generally increase the rate of \(\mathrm{S}_{\mathrm{N}} 1\) reactions. (d) \(\mathrm{S}_{\mathrm{N}} 2\) reaction of optically active substrate leads to racemization if the leaving group is attached to the chiral carbon.

Each question in this section has four suggested answers of which ONE OR MORE answers will be correct. Which of the following will give yellow precipitate when heated with powdered iodine and aqueous \(\mathrm{NaOH}\) ? (a) 2 -Butanol (b) 2-Methyl-2- propanol (c) 2-Pentanone (d) 3 -pentanol
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