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Chapter 4: Problem 2

(i) Suggest a method to prepare \(2-\) methyl \(-2\) - propanol using Grignard reagent. (ii) What happens when this alcohol is passed over copper heated to \(573 \mathrm{~K} ?\)

Short Answer

Expert verified
#Answer# 2-methyl-2-propanol can be prepared using a Grignard reagent by reacting methyl magnesium bromide with acetone. When this alcohol is passed over copper heated to 573 K, it undergoes dehydrogenation to form 2-methylpropene and water.

Step by step solution

01

Identify the Grignard reagent and the substrate

To prepare 2-methyl-2-propanol (C4H10O) using a Grignard reagent, we need to identify a suitable Grignard reagent and a substrate that will react to form the desired product. We can choose the Grignard reagent as methyl magnesium bromide (CH3MgBr) and the substrate as acetone (CH3COCH3).
02

Write the reaction

The reaction between methyl magnesium bromide (CH3MgBr) and acetone (CH3COCH3) can be written as: CH3MgBr + CH3COCH3 → (CH3)3COH + MgBrOH So, the method to prepare 2-methyl-2-propanol using Grignard reagent is to react methyl magnesium bromide with acetone. (ii) Reaction of 2-methyl-2-propanol when passed over heated copper:
03

Write the reaction

When 2-methyl-2-propanol is passed over copper heated to 573 K, it undergoes dehydrogenation (removal of hydrogen) to form an alkene. The reaction can be written as: C4H10O (2-methyl-2-propanol) → C4H8 (2-methylpropene) + H2O So, when 2-methyl-2-propanol is passed over heated copper at 573 K, it forms 2-methylpropene and water.

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Most popular questions from this chapter

\(\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{Br}+\mathrm{KI} \stackrel{\text { acetone }}{\longrightarrow} \mathrm{C}_{2} \mathrm{H}_{5}-\mathrm{I}+\mathrm{KBr} \quad \rightarrow(\mathrm{I})\) \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{C}-\mathrm{Br}+\mathrm{KI} \stackrel{\text { acetone }}{\longrightarrow}\left(\mathrm{CH}_{3}\right)_{3} \mathrm{C}-\mathrm{I}+\mathrm{KBr} \quad \rightarrow(\mathrm{II})\) Reaction (II) is much slower than reaction (I) because (a) \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CBr}\) is sparingly soluble in acetone. (b) (I) follows \(\mathrm{S}_{\mathrm{N}} 1\) and (II) follows \(\mathrm{S}_{\mathrm{N}} 2\) mechanism. (c) (I) follows \(\mathrm{S}_{\mathrm{N}} 2\) and (II) follows \(\mathrm{S}_{\mathrm{N}} 1\) mechanism. (d) steric hindrance in the case of reaction (II).

Which of the following is the correct order of ease of displacement of groups in substitution reactions? (a) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{SO}_{3}^{-}>\mathrm{CH}_{3} \mathrm{COO}^{-}>\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{O}\) (b) \(\mathrm{CH}_{3} \mathrm{COO}^{-}>\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{O}^{-}>\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{SO}_{3}^{-}\) (c) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{SO}_{3}^{-}>\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{O}^{-}>\mathrm{CH}_{3} \mathrm{COO}^{-}\) (d) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{O}^{-}>\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{SO}_{3}^{-}>\mathrm{CH}_{3} \mathrm{COO}^{-}\)

When 3,3-dimethyl-2-butanol is treated with dilute acid, the most stable carbocation formed is (a) 3,3-dimethyl-2-butyl cation (b) 3,3 -dimethyl-1-butyl cation (c) 2,3-dimethyl-2-butyl cation (d) 2-methyl-2-pentyl cation

2-Bromopentane \(\frac{\left(\mathrm{CH}_{3}\right)_{3} \operatorname{cok} /\left(\mathrm{CH}_{3}\right)_{3} \mathrm{COH}}{\longrightarrow} \mathrm{P}\) The major product (P) formed in the above reaction is (a) pent-1-ene (b) cis pent-2-ene (c) trans pent-2-ene

How is \(\left(\mathrm{C}_{6} \mathrm{H}_{5}\right)_{2} \mathrm{C}=\mathrm{CH}_{2}\) prepared by a Grignard reaction with \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{Br}\) and \(\mathrm{CH}_{3} \mathrm{COOC}_{2} \mathrm{H}_{5}\) as the starting materials?
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