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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

Dimethylamine(CH3) 2 NHhas a molecular weight of 45 and a boiling point of 7.40C. Trimethylamine, (CH3) 3N, has a higher molecular weight (59) but a lower boiling point(3.50C) . Explain this apparent discrepancy.

(a) How many asymmetric carbon atoms are there in an aldotetrose? Draw all the aldotetrose stereoisomers.

(b) How many asymmetric carbon atoms are there in a ketotetrose? Draw all the ketotetrose stereoisomers.

(c) How many asymmetric carbon atoms and stereoisomers are there for an aldohexose? For a ketohexose?

Some of the earliest synthetic detergents were the sodium alkyl sulfates, CH3(CH2)nCH2-OSO3-Na+ .Show how you would make sodium octadecylsulfate using tristearin as your organic starting material.

Question:

  1. Why do most long-chain fatty acids show a large peak in the mass spectrum at m/z 60 ?
  2. Use equations to explain the prominent peaks at m/z 74 and m/z 87 in the mass spectrum of 2-methylpentanoic acid.
  3. Why doesn鈥檛 the mass spectrum of 2-methylpentanoic acid show a large peak at m/z 60 ?

Question: A carboxylic acid has two oxygen atoms, each with two nonbonding pairs of electrons.

  1. Draw the resonance forms of a carboxylic acid that is protonated on the hydroxy oxygen atom.
  2. Compare the resonance forms with those given previously for an acid protonated on the carbonyl oxygen atom.
  3. Explain why the carbonyl oxygen atom of a carboxylic acid is more basic than the hydroxy oxygen.
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