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Question of 135

Q.Give chemical equation for the following reactions:

(i) Oxidation of propan-1-ol with alkaline KMnO4KMnO_4
(ii) Reaction of phenol with chloroform in presence of aqueous NaOH
(iii) Reaction of phenol with dil. HNO3HNO_3
(iv) Reaction of hydrogen iodide with methoxybenzene
(v) Formation of propoxypropane from propan-1-ol. OR How can the following changes be done? (Give chemical equations only):
(i) Propan-1-ol from ethyl magnesium chloride
(ii) 2-methyl propan-2-ol from methyl magnesium bromide
(iii) Benzoic acid from benzyl alcohol
(iv) Picric acid from phenol
(v) Dehydration of propan-2-ol.
Uttar Pradesh UpmspUP Board (UPMSP) Intermediate 2023Subjective· 5mImportance★★★★★
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Five equations from alcohols/phenols/ethers (main alternative of this OR): oxidation of propan-1-ol to propanoic acid; Reimer–Tiemann on phenol; nitration of phenol; cleavage of anisole by HI; and dehydration of propan-1-ol to dipropyl ether.

(i) Oxidation of propan-1-ol with alkaline KMnO4KMnO_4 (primary alcohol →\to carboxylic acid):

CH3CH2CH2OH→Δalk. KMnO4CH3CH2COOHCH_3CH_2CH_2OH \xrightarrow[\Delta]{alk.\ KMnO_4} CH_3CH_2COOH

(ii) Phenol + CHCl3CHCl_3 + aqueous NaOH (Reimer–Tiemann reaction): a −CHO-CHO group enters ortho to −OH-OH.

C6H5OH→then H3O+CHCl3, NaOH2-hydroxybenzaldehyde (salicylaldehyde)C_6H_5OH \xrightarrow[\text{then } H_3O^+]{CHCl_3,\ NaOH} \text{2-hydroxybenzaldehyde (salicylaldehyde)}

(iii) Phenol + dilute HNO3HNO_3 (nitration):

C6H5OH+HNO3 (dil.)→o-nitrophenol+p-nitrophenol+H2OC_6H_5OH + HNO_3\,(\text{dil.}) \rightarrow o\text{-nitrophenol} + p\text{-nitrophenol} + H_2O

(iv) Hydrogen iodide with methoxybenzene (anisole): the ether C–O bond breaks to give phenol and methyl iodide.

C6H5OCH3+HI→C6H5OH+CH3IC_6H_5OCH_3 + HI \rightarrow C_6H_5OH + CH_3I

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