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Chapter 20: Q9P. (page 1055)

Question: Draw all four resonance forms of the fragment at m/z 73 in the mass spectrum of pentanoic acid.

Short Answer

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Answer

The four resonance forms of the fragment at m/z 73 in pentanoic acid are shown:

Four resonance forms of pentanoic acid have fragments at m/z 73

Step by step solution

01

Mass spectrum

The mass spectrum is the representation in the form of a graph where the ratio of mass to charge is given and used to measure the mass when a molecular is converted into a gas phase ion. The fragments of the molecules are radical cations.

02

Resonance forms of the fragment at m/z 73 in pentanoic acid

The molecular weight of pentanoic acid is 102.13 g/mol. The fragment cleaved from pentanoic acid is -CH2CH3. It has a molecular mass of 29. The four resonance forms of the fragment at m/z 73 in pentanoic acid are shown as follows:

Four resonance forms of pentanoic acid have fragments at m/z 73

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Most popular questions from this chapter

Question: Give both IUPAC names and common names for the following compounds.

(a) phCH2COOH

(b) phCO2Na

(c) (CH3)2 CHCHCICOOH

(d) HOOC (CH2)4CO2H

(e) (CH3)2 CHCH2COOK

(f) CH3 CH(NH2) COOH

(g)

(h)

(i)

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.

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.

Question: Rank the following isomers in order of increasing boiling point, and explain the reasons for your order of ranking.

Question: Phenols are less acidic than carboxylic acids, with values of around 10. Phenols are deprotonated by (and therefore soluble in) solutions of sodium hydroxide but not by solutions of sodium bicarbonate. Explain how you would use extractions to isolate the three pure compounds from a mixture of p-cresol (p-methylphenol), cyclohexanone, and benzoic acid.
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