Organic Chemistry Basics - Result Question 170

####21. The IUPAC name of the compound

CH2=CHCH(CH3)2 is

(1987, 1M)

(a) 1,1-dimethyl-2-butene

(b) 3-methyl-1-butene

(c) 2-vinyl propane

(d) None of these

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Answer:

Correct Answer: 21. (d)

Solution:

  1. A mono-substituted benzoic acid is stronger than a mono-substituted phenol as former being a carboxylic acid. Among the given substituted benzoic acid, ortho-hydroxy acid is strongest acid although OH causes electron donation by resonance effect which tends to decrease acid strength.

It is due to a very high stabilisation of conjugate base by intramolecular H-bond which outweigh the electron donating resonance effect of OH.

The overall order of acid-strength of given four acids is ortho-hydroxybenzoic acid (pKa=2.98)> Toluic acid pKa=4.37)>p-hydroxybenzoic acid (pKa=4.58)> p-nitrophenol (pKa=7.15)



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