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Published on: 02/11/2019
Hydroxy Compounds and Ethers
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1.
Is it possible to oxidise t – butyl alcohol using acidified dichromate to form a carbonyl compound.
2.
Can we use nucelophiles such as NH3,CH3O - for the Nucleophilic substitution of alcohols
3.
Arrange the following in the increasing order of their boiling point and give a reason for your ordering
(i) Butan – 2- ol, Butan -1-ol, 2 –methylpropan -2-ol
(ii) Propan -1-ol, propan -1,2,3-triol, propan -1,3 – diol, propan -2-ol
4.
Predict the major product, when 2-methyl but -2-ene is converted into an alcohol in each of the following methods.
(i) Acid catalysed hydration
(ii) Hydroboration
(iii) Hydroxylation using Baeyer's reagent
5.
What is the major product obtained when two moles of ethyl magnesium bromide is treated with methyl benzoate followed by acid hydrolysis.
6.
Suggest a suitable reagent to prepare secondary alcohol with identical group using Grignard reagent.
7.
Draw the major product formed when 1-ethoxyprop-1-ene is heated with one equivalent of HI.
8.
Identify the product (s) is / are formed when 1 – methoxy propane is heated with excess HI. Name the mechanism involved in the reaction.
1.
Tertiary alcohols do not undergo oxidation reaction under normal conditions, but at elevated temperature under strong oxidizing, agent cleavage of C-C-bond takes place to give a mixture of carboxylic acid.
2.
Yes, we can use nucleophiles such as NH3, CH3O- for the nucleophilic substitution of alcohol.
Example
\(\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{OH}+\mathrm{NH}_{3} \rightarrow \mathrm{C}_{2} \mathrm{H}_{5} \mathrm{NH}_{2}+\mathrm{H}_{2} \mathrm{O} \)
\(\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{OH}+\mathrm{CH}_{2} \mathrm{~N}_{2} \rightarrow \mathrm{C}_{2} \mathrm{H}_{5} \mathrm{OCH}_{3}+\mathrm{N}_{2}\)
3.
(i) 2-methyl propan-2-o1 < Butan-2-ol < Butan-1-ol
(ii) propan-2-ol < propan-1-ol < propan -1,3- diol < propan-1,2,3-triol
4.
(i) Acid catalysed hydration
(ii) Hydroboration
(iii) Hydroxylation using Baeyer's reagent
5.
6.
Acetaldehyde - CH3-CHO
7.
8.
Since 1 - methoxy propane has primary alkyl group, it under goes SN2 reaction.
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