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Question: Name the following carboxylic acids (when possible, give both a common name and a systematic name).

(a)

(b)

(c)

(d)

(e)

(f)

Short Answer

Expert verified

(a) The IUPAC name is 2-iodo-3-methylpentanoic acid, and the common name is α-iodo-β-methylvalericacid.

(b) The IUPAC name is (Z)-3,4-dimethylhex-3-enoic acid, and there is no common name.

(c) The IUPAC name is 2,3-dinitrobenzoic acid, and there is no common name.

(d) The IUPAC name is trans-cyclohexane-1,2-dicarboxylic acid, and the common name is trans-hexahydrophthalic acid.

(e) The IUPAC name is 2-chlorobenzene-1,4-dicarboxylic acid, and the common name is 2-chloroterephthalic acid.

(f) The IUPAC name is 3-methylhexanedioic acid, and the common name isβ-methyladipic

Step by step solution

01

Nomenclature of carboxylic acids

Carboxylic acids are compounds that end with –oic acid, and if two carboxyl groups are present, the name ends with –dioic acid.The IUPAC name for HCOOH is methanoic acid, and the common name is formic acid.

02

Naming of carboxylic acids

(a) The IUPAC name is 2-iodo-3-methylpentanoic acid because the iodine group is present at the 2ndposition, and the methyl groups are present at the third position. The total number of carbons in a chain is5. The common name is α-iodo-β-methylvalericacid.




(b) The IUPAC name is (Z)-3,4-dimethylhex-3-enoic acid:Z is for cis alkene, and the methyl groups are present at the 3rd and 4th positions. There is no common name.


(c) The IUPAC name is 2,3-dinitrobenzoic acid, and the nitro groups are present at the 2nd and 3rd positions in the benzene ring. There is no common name.



03

Naming of carboxylic acids

(d) The IUPAC name is trans-cyclohexane-1,2-dicarboxylic acid. One COOH group is above the plane, and one COOH group is below the plane.The common name is trans-hexahydrophthalic acid.



(e) The IUPAC name is 2-chlorobenzene-1,4-dicarboxylic acid;the chloro group is present at the 2nd position, and the two COOH groups are present at the 1st and 4th positions.The common name is 2-chloroterephthalic acid.

(f) The IUPAC name is 3-methylhexanedioic acid,and one methyl group is present at the 3rd position.The common name is β-methyladipic.




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Most popular questions from this chapter

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’t the mass spectrum of 2-methylpentanoic acid show a large peak at m/z 60 ?

The 2000 Nobel Prize in Chemistry was awarded for work on polyacetylenes. Acetylene can be polymerized using a Ziegler-Natta catalyst. The cis or trans stereochemistry of the products can be controlled by careful selection and preparation of the catalyst. The resulting polyacetylene is an electrical semiconductor with a metallic appearance. cis-Polyacetylene has a copper color, and trans-polyacetylene is silver.

(a) Draw the structures of cis- and trans-polyacetylene.

(b) Use your structures to show why these polymers conduct electricity.

(c) It is possible to prepare polyacetylene films whose electrical conductivity is anisotropic. That is, the conductivity is higher in some directions than in others. Explain how this unusual behavior is possible.

Explain why the acid-catalyzed condensation is a poor method for the synthesis of an unsymmetrical ether such as ethyl methyl ether, CH3CH2 - O - CH3.

(a) Propose a mechanism for the following reaction:

(b) Use the bond-dissociation enthalpies given in Table 4-2 (page 203) to calculate the value of ∆H° for each step shown in your mechanism. (The BDE for is about 280 kJ/mol, or 67 kcal/mol.) Calculate the overall value of ∆H° for the reaction. Are these values consistent with a rapid free-radical chain reaction?

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, α-bromobutyric acid, β-bromobutyric acid

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