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Chapter 26: Problem 73

Draw as many structural isomers as you can for cyclic ethers (no - OH groups) having the formula \(\mathrm{C}_{4} \mathrm{H}_{6} \mathrm{O}\) Try to draw at least six. (There are more than six.).

Short Answer

Expert verified
There are several potential isomers for the compound \(\mathrm{C}_{4} \mathrm{H}_{6} \mathrm{O}\) when specified by cyclic ethers. The specifics of the isomers depend on the configuration and bonding of the carbon, hydrogen and oxygen atoms.

Step by step solution

01

- Generate Possible Structures

Using the formula, imagine how four carbon atoms, six hydrogen atoms, and an oxygen atom can be joined together. Remember that carbon usually forms 4 bonds, oxygen usually forms 2, and hydrogen forms 1. The first isomer could be a 5-membered ring with four carbons and one oxygen. The remaining two hydrogens can be attached to any carbon in any possible combination.
02

- Generate More Isomers

To generate more isomers, we can move the position of the hydrogen atoms around the ring or change the size of the ring. For example, another isomer can be made by having a three-membered ring with two carbons and an oxygen atom. The remaining two carbon atoms can be attached as a side chain, with hydrogens added accordingly.
03

- Draw All Possible Isomers

Continue to experiment with different configurations of the atoms to create additional isomers. Remember, the oxygen atom must be part of the ring and there should not be any hydroxy (-OH) groups according to the given criteria.
04

- Verify Isomers

Once all possible isomers are drawn, count the number of carbons, hydrogens and oxygen in each structure to ensure they match the given formula \(\mathrm{C}_{4} \mathrm{H}_{6} \mathrm{O}\). The structures must also adhere to the rules of covalent bonding.

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Most popular questions from this chapter

Supply condensed structural formulas for the following substances. (a) 2,4,6 -trinitrotoluene (TNT-an explosive) (b) methyl salicylate (oil of wintergreen) [Hint: Salicylic acid is \(o \text { -hydroxybenzoic acid. }]\) (c) 2 -hydroxy-1,2,3-propanetricarboxylic acid (citric \(\left.\operatorname{acid}, \mathrm{C}_{6} \mathrm{H}_{8} \mathrm{O}_{7}\right)\).

Draw the structure for each of the following. (a) \((R)-1\) -bromo-1-chloroethane (b) ( \(E\) )-2-bromo-2-pentene (c) \((Z)-1-\) chloro- 3 -ethyl- 3 -heptene (d) \((R)\) -2-hydroxypropanoic acid (e) ( \(S\) )-2-aminopropanoate anion.

Give the noncyclic isomers with molecular formula \(\mathrm{C}_{4} \mathrm{H}_{8} \mathrm{O}_{2}\) that contain more than one functional group.

Supply condensed structural formulas for the following substances. (a) \(o\) -tert-butylphenol (an antioxidant in aviation gasoline) (b) 1 -phenyl- 2 -aminopropane (benzedrine-an amphetamine, ingredient in "pep pills") (c) 2 -methylheptadecane (a sex pheromone of tiger moths-a chemical used for communication among members of the species) [ Hint: Heptadeca means 17.].

Supply a name or structural formula for each of the following. (a) phenylacetylene (b) \(m\) -dichlorobenzene
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