Arrange 1-butanol, 2-butanol, and 2-methyl-2-propanol in order of increasing aci

Question

Arrange 1-butanol, 2-butanol, and 2-methyl-2-propanol in order of increasing acidity. What is the conjugate base of each of these alcohols? What reaction occurs when the conjugate base of any alcohol is placed in water?


Order of Acidity: __________________________________________________


Conjugate Bases: _________________________________________________


Rxn. w. Water:     _________________________________________________


5. Why do alcohols dissolve in concentrated HCl? Why are alkyl halides insoluble in concentrated HCl ?

Explanation / Answer

acidity increases in the order: Primary alcohol> Secondary alcohol> tertiary alcohol

therefore 1-butanol is primary alcohol, 2-butanol is secondary alcohol and 2-methyl2-butanol is tertiary alcohol

among them 1-butanol has highest acid than others.

the order is 1-butanol>2butanol>2methyl 2-propanol

due to increase of alkyl group (electron donation groups) hence H+ ion not remove easily hence acidic character decreases for tertiary alcohol

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when conjucate base of alcohol react with water to give water and hydroxyl ions

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stronger acid its base is weaker conjucate base

hence Strongest acid is a weakest conjucate base the order is given below

2-methyl-2-propanol>2-butanol> 1-butanol

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alkyl halide do not soluble in Concentrated HCl due common ion effect hence precipitation takes place but in alkyl halide undergo nucleophilic substitution reaction occur.

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