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draw the mechanism for when tert-pentyl alcohol reacts with iodoform test

draw the mechanism for when tert-pentyl alcohol reacts with iodoform test

Organic Chemistry
Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter23: Carbonyl Condensation Reactions
Section23.SE: Something Extra
Problem 71AP
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draw the mechanism for when tert-pentyl alcohol reacts with iodoform test 

Test Jones' Oxidation 2,4- Dinitrophenyl- hydrazones Purpald lodoform Tests for Primary and secondary Alcohols, Aldehydes Aldehydes and Ketones 29010 Aldehydes Methyl Ketones and Methyl Alcohols Procedure Add 2 drops of the unknown to 0.5 mL of pure acetone in a test tube, and add to this solution 1 small drop of Jones' reagent (chromic acid in sulfuric acid). A positive test is formation of a green color within 5 sec upon addition of the orange-yellow reagent to a primary or secondary alcohol. Add 3 drops of the unknown to 0.5 mL of ethanol, and then add 0.75 mL of 2,4-dinitrophenylhydrazine reagent. Mix thoroughly and let sit for a few minutes. A yellow to red precipitate is a positive test. Yellow derivatives are formed from compounds with isolated carbonyl groups and orange- red to red derivatives from aldehydes or ketones conjugated with double bonds or aromatic rings. Add 2 drops of your unknown to 1 mL of purpald reagent. Add one drop of 3% H₂O₂ and shake. Aldehydes develop a purple/brown color. This may take a few minutes. Ketones will remain colorless. Dissolve 4 drops of unknown in 2 mL of water (if water soluble) or in 2 mL of 1,2-dimethoxyethane (if water insoluble). Then add 2 mL of 3M NaOH and slowly add 3 mL of the iodine solution. In a positive test the brown color of the reagent disappears, and the yellow iodoform separates.
Transcribed Image Text:Test Jones' Oxidation 2,4- Dinitrophenyl- hydrazones Purpald lodoform Tests for Primary and secondary Alcohols, Aldehydes Aldehydes and Ketones 29010 Aldehydes Methyl Ketones and Methyl Alcohols Procedure Add 2 drops of the unknown to 0.5 mL of pure acetone in a test tube, and add to this solution 1 small drop of Jones' reagent (chromic acid in sulfuric acid). A positive test is formation of a green color within 5 sec upon addition of the orange-yellow reagent to a primary or secondary alcohol. Add 3 drops of the unknown to 0.5 mL of ethanol, and then add 0.75 mL of 2,4-dinitrophenylhydrazine reagent. Mix thoroughly and let sit for a few minutes. A yellow to red precipitate is a positive test. Yellow derivatives are formed from compounds with isolated carbonyl groups and orange- red to red derivatives from aldehydes or ketones conjugated with double bonds or aromatic rings. Add 2 drops of your unknown to 1 mL of purpald reagent. Add one drop of 3% H₂O₂ and shake. Aldehydes develop a purple/brown color. This may take a few minutes. Ketones will remain colorless. Dissolve 4 drops of unknown in 2 mL of water (if water soluble) or in 2 mL of 1,2-dimethoxyethane (if water insoluble). Then add 2 mL of 3M NaOH and slowly add 3 mL of the iodine solution. In a positive test the brown color of the reagent disappears, and the yellow iodoform separates.
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