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Chapter 22: Problem 111

Draw the following incorrectly named compounds and name them correctly. a. 2 -ethyl-3-methyl-5-isopropylhexane b. 2 -ethyl-4-tert-butylpentane c. 3 -methyl-4-isopropylpentane d. 2 -ethyl-3-butyne

Short Answer

Expert verified
The correct names and structures for the given compounds are as follows: a. 2-ethyl-3-methyl-5-propylhexane b. 2-ethyl-4-(1,1-dimethylethyl)pentane c. 3-methyl-4-propylpentane d. 4-ethyl-1-butyne

Step by step solution

01

Identify errors in compound a name

The given molecule name is 2-ethyl-3-methyl-5-isopropylhexane. Since the isopropyl group is used when naming side chains, it should not be used in the context of the main chain. Let's fix this and draw the compound. ### Step 2: Draw and name compound a correctly ###
02

Draw and name compound a correctly

First, we'll draw the carbon skeleton of hexane with the given substituents. Then, rename the molecule, replacing the isopropyl group with its proper name of "propyl." This results in the correct name: 2-ethyl-3-methyl-5-propylhexane. ### Step 3: Identify errors in compound b usage ###
03

Identify errors in compound b name

The given molecule name is 2-ethyl-4-tert-butylpentane. However, as with compound a, using the tert-butyl group naming in main carbon chain is not an appropriate IUPAC naming convention. Let's fix this and draw the compound. ### Step 4: Draw and name compound b correctly ###
04

Draw and name compound b correctly

Draw the carbon skeleton of pentane with the given substituents. Then, rename the tert-butyl group with the name "1,1-dimethylethyl" to fit the IUPAC naming convention. This results in the correct name: 2-ethyl-4-(1,1-dimethylethyl)pentane. ### Step 5: Identify errors in compound c usage ###
05

Identify errors in compound c name

The given molecule name is 3-methyl-4-isopropylpentane. Just as in the previous cases, using the isopropyl group does not follow the IUPAC naming convention. Let's fix this by drawing and naming the compound correctly. ### Step 6: Draw and name compound c correctly ###
06

Draw and name compound c correctly

Draw the carbon skeleton of pentane with the given substituents. Then, rename the molecule, replacing the isopropyl group with the name "propyl," the correct choice according to IUPAC nomenclature. This results in the correct name: 3-methyl-4-propylpentane. ### Step 7: Identify errors in compound d usage ###
07

Identify errors in compound d name

The given molecule name is 2-ethyl-3-butyne. However, the numbering in the main chain is incorrect, as the triple bond should have the lowest number priority. Let's correct this and redraw the molecule. ### Step 8: Draw and name compound d correctly ###
08

Draw and name compound d correctly

Draw the carbon skeleton of butyne and add the ethyl substituent to the correct position. Renumber the molecule in a way that the triple bond has the lowest number priority. This results in the correct name: 4-ethyl-1-butyne.

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Most popular questions from this chapter

Ethylene oxide, is an important industrial chemical. Although most ethers are unreactive, ethylene oxide is quite reactive. It resembles \(\mathrm{C}_{2} \mathrm{H}_{4}\) in its reactions in that addition reactions occur across the \(\mathrm{C}-\mathrm{O}\) bond in ethylene oxide. a. Why is ethylene oxide so reactive? (Hint: Consider the bond angles in ethylene oxide as compared with those predicted by the VSEPR model.) b. Ethylene oxide undergoes addition polymerization, forming a polymer used in many applications requiring a nonionic surfactant. Draw the structure of this polymer.

Draw the structures for two examples of unsaturated hydrocarbons. What structural feature makes a hydrocarbon unsaturated?

Polycarbonates are a class of thermoplastic polymers that are used in the plastic lenses of eyeglasses and in the shells of bicycle helmets. A polycarbonate is made from the reaction of bisphenol A (BPA) with phosgene \(\left(\mathrm{COCl}_{2}\right)\) : polycarbonate \(+2 n \mathrm{HCl}\) Phenol \(\left(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{OH}\right)\) is used to terminate the polymer (stop its growth). a. Draw the structure of the polycarbonate chain formed from the above reaction. b. Is this reaction a condensation or an addition polymerization?

What are the structural differences between \(\alpha\) - and \(\beta\) -glucose? These two cyclic forms of glucose are the building blocks to form two different polymers. Explain.

The base sequences in mRNA that code for certain amino acids are Glu: \(\quad\) GAA, GAG Val: GUU, GUC, GUA, GUG Met: \(\quad\) AUG Trp: \(\quad\) UGG Phe: UUU, UUC Asp: \(\quad\) GAU, GAC These sequences are complementary to the sequences in DNA. a. Give the corresponding sequences in DNA for the amino acids listed above. b. Give a DNA sequence that would code for the peptide trp-glu-phe-met. c. How many different DNA sequences can code for the tetrapeptide in part \(\mathrm{b}\) ? d. What is the peptide that is produced from the DNA sequence \(\mathrm{T}-\mathrm{A}-\mathrm{C}-\mathrm{C}-\mathrm{T}-\mathrm{G}-\mathrm{A}-\mathrm{A}-\mathrm{G} ?\) e. What other DNA sequences would yield the same tripeptide as in part \(\mathrm{d}\) ?
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