Rank the acids in order of increasing acid strength: CH3CH2CH2CHBrCOOH (1), CH3CH2CHBrCH2COOH (2), CH3CHBrCH2CH2COOH (3) Group of answer choices 3<2<1 3<1<2 2<1<3 2<3<1 1<2<3 1<3<2

Question

Chemistry

Allyson Buck

18 July, 10:05

Rank the acids in order of increasing acid strength: CH3CH2CH2CHBrCOOH (1), CH3CH2CHBrCH2COOH (2), CH3CHBrCH2CH2COOH (3) Group of answer choices 3<2<1 3<1<2 2<1<3 2<3<1 1<2<3 1<3<2

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Answers (1)

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Charlie Vega · Answer 1

3 < 2 < 1.

Explanation:

Inductive effect:

Electron (sigma) displacement towards the highly electronegative atom (eg. Cl-, Br-, - NO2 etc) where one end becomes positively charge and the other becomes negatively charge.

In organic carboxylic acids, an electronegative substituent can pull electron density out of an acidic bond through the inductive effect making it electron deficient, resulting in acidity. This effect decreases, the further the electronegative element is from the carboxylate group (-COOH).

1. CH3CH2CH2CHBrCOOH

2. CH3CH2CHBrCH2COOH

3. CH3CHBrCH2CH2COOH

In decreasing acidity,

1 > 2 > 3

While in increasing acidity,

3 < 2 < 1