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Chapter 20: Q3P. (page 1047)

Question: Rank the compounds in each set in order of increasing acid strength.

(a)CH3CH2COOH,CH3CHBrCOOH,CH3CBr2COOH

(b) CH3CH2CH2CHBrCOOH,CH3CH2CHBrCH2COOH,CH3CHBrCH2CH2COOH

(c)

,CH3CH2COOH,

Short Answer

Expert verified

(a)

(b)

(c)

Step by step solution

01

Acid strength

Acidic strength depends on the electron-withdrawing group; a greater number of electron-withdrawing groups increases the acidity of a compound.The electron-withdrawing group stabilizesthe carboxylate anion.

02

Order of increasing acid strength

(a) The greater the number of electron-withdrawing substituents present in the compound, the morethe carboxylate ion will stabilize. So, the compound with two bromine groups has the strongest acidic strength.



Order of increasing acid strength

03

Order of increasing acid strength

(b) The closer the electron-withdrawing substituents are to the carboxyl group, the greater will be the stabilization of the carboxylate ion. So, the compound with the bromine group closer to the carboxyl group has the strongest acidic strength.


Order of increasing acid strength

04

Order of increasing acid strength

(c) The stronger the electron-withdrawing group, the greater the carboxylate ion's stabilization is. So, the compound with the nitro group has the strongest acidic strength because it is the strongest electron-withdrawing group.



Order of increasing acid strength

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Most popular questions from this chapter

Grignard reagents add to carbonate esters as they add to other esters.

(a) Predict the major product of the following reaction.

(b) Show how you would synthesize 3-ethylpentan-3-ol using diethyl carbonate and ethyl bromide as your only organic reagents.

(c) Diethyl carbonate is a liquid reagent that is easy to handle. In contrast, phosgene is a highly toxic and corrosive gas. Show how you might use diethyl carbonate instead of phosgene to make Lexan庐. Also, show how you might use diethyl carbonate instead of methyl isocyanate to make Sevin庐 insecticide.

The reaction of tert-butyl alcohol with concentrated HCl goes by the SN1 mechanism. Write a mechanism for this reaction.

The following reaction takes place under second-order conditions (strong nucleophile), yet the structure of the product shows rearrangement. Also, the rate of this reaction is several thousand times faster than the rate of substitution of hydroxide ion on 2-chlorobutane under similar conditions. Propose a mechanism to explain the enhanced rate and rearrangement observed in this unusual reaction. (鈥淓t鈥� is the abbreviation for ethyl.

Show how you would synthesize the following compounds, starting with acetylene and any compounds containing no more than four carbon atoms.

(a)hex-1-yne

(b)hex-2-yne

(c)cis-hex-2-ene

(d)trans-hex-2-ene

(e)1,1-dibromohexane

(f)2,2-dibromohexane

(g)pentanal, CH3CH2CH2CH2CHO

(h)pentan-2-one, CH3-CO-CH 2CH2 CH3

(i) (+/)-3,4-dibromohexane

(j)meso-butan-2,3-diol

(k)2-methylhex-3-yn-2-ol

In the presence of 18-crown-6, potassium permanganate dissolves inbenzene to give 鈥減urple benzene鈥� a useful reagent for oxidizing alkenes in an aprotic environment. Use a drawing of the complex to show why dissolves in benzeneand why the reactivity of the permanganate ion is enhanced.
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