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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 iodomethylvalericacid.

(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 is methyladipicacid.

Step by step solution

01

Nomenclature of carboxylic acids

Carboxylic acids are compounds that end with 鈥搊ic acid, and if two carboxyl groups are present, the name ends with 鈥揹ioic 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 2nd position, and the methyl groups are present at the third position. The total number of carbons in a chain is 5. The common name is iodomethylvalericacid.


(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 methyladipicacid.

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Most popular questions from this chapter

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).

Glutathione (GSH) is a tripeptide that serves as a mild reducing agent to detoxify peroxides and maintain the cysteine residues of hemoglobin and other red blood cell proteins in the reduced state. Complete hydrolysis of glutathione gives Gly, Glu, and Cys. Treatment of glutathione with carboxypeptidase gives glycine as the first free amino acid released. Treatment of glutathione with 2,4-dinitrofluorobenzene (Sanger reagent, Problem 24-21, page 1282), followed by complete hydrolysis, gives the 2,4-dinitrophenyl derivative of glutamic acid. Treatment of glutathione with phenyl isothiocyanate does not give a recognizable phenylthiohydantoin, however.

(a) Propose a structure for glutathione consistent with this information. Why would glutathione fail to give a normal product from Edman degradation, even though it gives a normal product from the Sanger reagent followed by hydrolysis?

(b) Oxidation of glutathione forms glutathione disulfide(GSSG). Propose a structure for glutathione disulfide, and write a balanced equation for the reaction of glutathione with hydrogen peroxide.

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.

Show how you would synthesize the following compounds, starting with acetylene and any compounds containing no more than four carbon atoms.

(a)hex-1-yne

(b)hex-2-yne

(c)cis-hex-2-ene

(d)trans-hex-2-ene

(e)1,1-dibromohexane

(f)2,2-dibromohexane

(g)pentanal, CH3CH2CH2CH2CHO

(h)pentan-2-one, CH3-CO-CH 2CH2 CH3

(i) (+/)-3,4-dibromohexane

(j)meso-butan-2,3-diol

(k)2-methylhex-3-yn-2-ol

Show how you would accomplish the following syntheses. Some of these conversions may require more than one step.

(a) isopentyl alcohol isopentyl acetate (banana oil)

(b) 3-ethylpentanoic acid3-ethylpentanenitrile

(c) isobutylamineN-isobutylformamide

(d) ethyl acetate3-methylpentan-3-ol

(e) cyclohexylamineN-cyclohexylacetamide

(f) bromocyclohexanedicyclohexylmethano

(g)

(h)

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