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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

Most of the Fischer esterification mechanism is identical with the mechanism of acetal formation. The difference is in the final step, where a resonance-stabilized carbocation loses a proton to give the ester. Write mechanisms for the following reactions, with the comparable steps directly above and below each other. Explain why the final step of the esterification (proton loss) cannot occur in acetal formation, and show what happens instead.

Given the structure of ascorbic acid (vitamin C):

(a) Is ascorbic acid a carboxylic acid?

(b) Compare the acid strength of ascorbic acid (pKa=4.71) with acetic acid.

(c) Predict which proton in ascorbic acid is the most acidic.

(d) Draw the form of ascorbic acid that is present in the body (aqueous solution, pH = 7.4).

When pure (S)-lactic acid is esterified by racemic butan-2-ol, the product is 2-butyl lactate, with the following structure:

(a)Draw three-dimensional structures of the two stereoisomers formed, specifying the configuration at each asymmetric carbon atom. (Using your models may be helpful.)

(b)Determine the relationship between the two stereoisomers you have drawn.

Suggest how you would convert trans-4-methylcyclohexanol to

(a) trans-1-chloro-4-methylcyclohexane.

(b) cis-1-chloro-4-methylcyclohexane.

Question: Arrange each group of compounds in order of increasing acidity.

  1. phenol, ethanol, acetic acid
  2. p-toluenesulfonic acid, acetic acid, chloroacetic acid
  3. benzoic acid, o-nitrobenzoic acid, m-nitrobenzoic acid
  4. butyric acid, 伪-bromobutyric acid, 尾-bromobutyric acid
See all solutions

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