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Chapter 11: Q32P (page 574)

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

Both cis- and trans-2-methylcyclohexanol undergo dehydration in warm sulfuric acid to give 1-methylcyclohexene as the major alkene product. These alcohols can also be converted to alkenes by tosylation usingand pyridine, followed by elimination using KOC(CH3)3as a strong base. Under these basic conditions, the tosylate of cis-2-methylcyclohexanol eliminates to give mostly 1-methylcyclohexene, but the tosylate of trans-2-methylcyclohexanol eliminates to give only 3-methylcyclohexene. Explain how this stereochemical difference in reactants controls a regiochemical difference in the products of the basic elimination, but not in the acid-catalyzed elimination.

Give the structures of the products you would expect when each alcohol reacts with

(1) HCl, ZnCl2; (2) HBr; (3) PBr3; (4) P/I2; and (5) SOCl2.

(a) butan-1-ol (b) 2-methylbutan-2-ol

(c) 2,2-dimethylbutan-1-ol (d) cis-3-methylcyclopentanol

When cis-2-methylcyclohexanol reacts with the Lucas reagent, the major product is 1-chloro-1-methylcyclohexane. Propose a mechanism to explain the formation of this product.

Two unknowns, X and Y, both having the molecular formula C4H8O , give the following results with four chemical tests. Propose structures for X and Y consistent with this information.

Bromine

Na metal

Chromic acid

Lucas reagent

Compound X

decolorizes

Bubbles

orange to green

no reaction

Compound Y

no reaction

no reaction

no reaction

no reaction

Show how you would convert butan-1-ol to the following compounds using tosylate intermediates. You may use whatever additional reagents are needed.

(a)1-bromobutane (b)butan-1-amine, CH3CH2CH2CH2NH2

(c)butyl ethyl ether, CH3CH2CH2CH2OCH2CH3 (d)pentannitrile, CH3CH2CH2CH2CN
See all solutions

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