Use resonance forms of the conjugate bases to explain why methanesulfonic acid (CH3SO3H,pKa= -2.6) is a much stronger acid than acetic acid (CH3COOH,pKa =4.8)

Short Answer

Expert verified

Methane sulfonic acid is a stronger acid than acetic acid as it is highly stabilized by the resonance structures and the inductive effect.

Step by step solution

01

Resonance forms

Resonance structures constitute structures that explain the electron delocalization in a particular molecule. A molecule comprising several resonance structures possesses significant stability.

02

Acidic Strength

Numerous factors impact the acidic strength, and some of them include resonance and inductive effect. The conjugate base stability is more significant for a molecule comprising resonance effect, and such molecules are acidic.

03

Resonance forms to explain why methanesulfonic acid is a stronger acid than acetic acid

The acidic strength decides the stability of a conjugate base. The acid comprising a more stable conjugate base is highly stable.

The methanesulfonate ion is stabilized by resonance and induction. It has three resonance structures. The sulfur atom is more electronegative than carbon and comprises a small role in stabilizing the negative charge on carbon.

The acetate ion has two resonance structures. It does not have an inductive effect to stabilize the anion. The resonance structures of acetate ion and methylsulfonate ion can be given as:

Resonance structures of acetate and methylsulfonate ion

Acetic acid is a mild acid, but methanesulfonic acid is stronger than acetic acid.

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Most popular questions from this chapter

Give the structure of the principal product(s) when each of the following alcohols reacts with (1) Na2Cr2O7/H2SO4 (2) PCC, (3) DMP, and (4) 1 equiv NaOCl-TEMPO.

(a)octan-1-ol (b)octan-3-ol

(c) 4-hydroxydecanal (d) 1-methylcyclohexan-1,4-diol

(a) The reaction of butan-2-ol with concentrated aqueous HBr goes with partial racemization, giving more inversion than retention of configuration. Propose a mechanism that accounts for racemization with excess inversion.

(b)Under the same conditions, an optically active sample of trans-2-bromocyclopentanol reacts with concentrated aqueous HBr to give an optically inactive product, (racemic) trans-1,2-dibromocyclopentane. Propose a mechanism to show how this reaction goes with apparently complete retention of configuration, yet with racemization. (Hint: Draw out the mechanism of the reaction of cyclopentene with in water to give the starting material, trans-2- bromocyclopentanol. Consider how parts of this mechanism might be involved in the reaction with HBr.)

Predict the esterification products of the following acid/alcohol pairs.

(a) CH3CH2COOH + CH3OH

(b) CH3CH2OH + HNO3

(c) 2CH3CH2CH2OH + H3PO4

(d)

(e)

Suggest the most appropriate method for each of the following laboratory syntheses. In each case, suggest both a chromium reagent and a chromium-free reagent

(a) butan - 1 - ol → butanal, CH3CH2CH2CHO

(b) but - 2 - en - 1 - ol → but - 2 - enoic acid, CH3CH = CHCOOH

(c) butan - 2 - ol → butan - 2 - one, CH3COCH2CH3

(d) cyclopentanol → 1 - cyclopentylpropan - 1 - ol (twosteps)

(e) cyclopentyclohexanol → 2 - methylcyclohexanone (several steps)

(f) 1 - methylcyclohexanol → 2 - methylcyclohexanone (several steps)

Predict the major products of the following reactions.

(a)ethyl tosylate+potassium tert-butoxide

(b) isobutyl tosylate + NaI

(c) (R)-2-hexyl tosylate + NaCN

(d) the tosylate of cyclohexylmethanol +excess NH3

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