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Chapter 20: Q19 Pb (page 1066)

Show how you would synthesize the following compounds from the appropriate carboxylic acids or acid derivatives.

a)


b)



c)

Short Answer

Expert verified

a)


b)

c)

Step by step solution

01

Carboxylic acids or acid derivatives 

Carboxylic acids are the COOH- containing compounds, and acid derivatives are the compounds formed when the OH group of a carboxylic acid is replaced by Cl (acid chloride) or - NH2(amide). There are three types of acid derivatives: acid halides, esters, and amides.

02

Synthesis of phenylacetic acid 

(a) Isopropyl alcohol is synthesized when phenylacetic acid is treated with LiAlH4 and further with H3O+. Another method is by treating phenylacetic acid with B2H6 and then with H3O+.


Synthesis of phenylacetic acid

03

Synthesis of phenylacetaldehyde 

Phenylacetaldehyde is synthesized when phenylacetyl chloride is treated with LiAIH(O - t - Bu)3and further with H3O+ .

04

Formation of phenylacetaldehyde 

Synthesis of phenylacetaldehyde

05

Synthesis of compounds 

The COOH group of a reactant is converted to CH2OH-when the reactant is treated with B2H6 and further with H3O+ .

06

Formation of compounds 

Synthesis of alcoholic compounds

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Most popular questions from this chapter

The IR, NMR, and mass spectra are provided for an organic compound.

  1. Consider each spectrum individually, and tell what characteristics of the molecule are apparent from that spectrum.
  2. Propose a structure for the compound, and show how your structure fits the spectral data.
  3. Explain why an important signal is missing from the proton NMR spectrum.

Predict the major products formed when the following amines undergo exhaustive methylation, treatment with Ag2O, and heating.

  1. Hexan-2-amine
  2. 2-methylpiperidine
  3. N-ethylpiperidine

5.

6.

Predict the productsand propose mechanisms for the following reactions.

Question: Show the products you expect when each compound reacts with NBS with light shining on the reaction.

a)

Question: Oxidation of a primary alcohol to an aldehyde usually gives some over-oxidation to the carboxylic acid. Assume you have used PCC to oxidize pentan-1-ol to pentanal.

(b). Which of the expected impurities cannot be removed from pentanal by acid-base extractions? How would you remove this impurity?
See all solutions

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