Conversion Of Primary Alcohols Into Secondary And Tertiary Alcohols
Description
This section is from the book "Alcohol, Its Production, Properties, Chemistry, And Industrial Applications", by Charles Simmonds. Also available from Amazon: Alcohol: Its Production, Properties, Chemistry, And Industrial Applications.
Conversion Of Primary Alcohols Into Secondary And Tertiary Alcohols
On distillation with dehydrating agents, e.g., sulphuric acid or zinc chloride, primary alcohols have the elements of water removed and yield unsaturated hydrocarbons: -
CH3.CH1 .CH1.OH | - | H1O | = | CH3.CH:CH1. |
Propyl alcohol. | Propylene. |
On treating the hydrocarbon with concentrated hydriodic acid, the iodine atom attaches itself to the carbon having least hydrogen, forming a secondary iodide: -
CH3.CH:CH1 | + | HI | = | CH3.CHI.CH3 |
Propylene. | Isopropyl iodide. |
When the iodide is treated with moist silver oxide, the iodine atom is replaced by a hydroxyl group according to the general method (1), above, thus yielding a secondary alcohol: the resulting product would have been a tertiary alcohol: -
CH3 .CHI.CH3 + AgOH = CH3.CH(OH).CH3 + Agl.
If, instead of starting with propyl alcohol, we had taken isobutyl alcohol, which contains the primary group -CH1.OH united to a secondary radical
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