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Chapter 23: Problem 582

Write structures for each of the following names: (a) m-cresol (b) 3 -hydroxybenzenesulfonamide (c) 3 -chloro-1, 2 -benzoquinone (d) o-methoxyphenol (e) \(\mathrm{p}(\mathrm{t}-\) tolyl \()\) azophenol (f) benzyl pheny 1 ether (g) \(3-\) (o-hydroxy phenyl pentanoic acid) (h) 2 -methoxy-1, 4 -naphthoquinone

Short Answer

Expert verified
The structures for the given compound names are: (a) m-cresol: \( HO-C_{6}H_{4}-CH_{3} \) (b) 3-hydroxybenzenesulfonamide: \( NH_{2}-SO_{2}-C_{6}H_{4}-OH \) (c) 3-chloro-1,2-benzoquinone: \( O=C-C_{6}H_{3}-C(=O)-Cl \) (d) o-methoxyphenol: \( HOC_{6}H_{4}-OCH_{3} \) (e) p(t-tolyl)azophenol: \(C_{7}H_{7}-N=N-C_{6}H_{4}-OH \) (f) benzyl phenyl ether: \( C_{6}H_{5}-O-CH_{2}-C_{6}H_{5} \) (g) 3-(o-hydroxy phenyl pentanoic acid): \( HO-C_{6}H_{4}-CH_{2}-CH_{2}-CH_{2}-CH_{2}-COOH \) (h) 2-methoxy-1,4-naphthoquinone: \( O=C-C_{10}H_{5}-C(=O)-OCH_{3} \)

Step by step solution

01

(a) m-cresol

To draw the structure for m-cresol, we need to know that cresol is a methylated phenol, and the "m" indicates a substitution on the meta position. This gives us a phenol with a methyl group on the meta position, which is in position 3. The structure for m-cresol is: \[ HO-C_{6}H_{4}-CH_{3} \]
02

(b) 3-hydroxybenzenesulfonamide

To draw the 3-hydroxybenzenesulfonamide structure, we need to start with the benzenesulfonamide. A sulfonamide group is attached to benzene. The hydroxybenzene part indicates a hydroxyl group on the benzene ring, and with the number 3, the hydroxyl group is in position 3. The structure for 3-hydroxybenzenesulfonamide is: \[ NH_{2}-SO_{2}-C_{6}H_{4}-OH \]
03

(c) 3-chloro-1,2-benzoquinone

To draw the 3-chloro-1,2-benzoquinone structure, we need to know that benzoquinone is a benzene ring with two carbonyl groups on position 1 and 2. The 3-chloro adds a chlorine atom to position 3. The structure for 3-chloro-1,2-benzoquinone is: \[ O=C-C_{6}H_{3}-C(=O)-Cl \]
04

(d) o-methoxyphenol

To draw the structure for o-methoxyphenol, we need to know that the "o" stands for ortho, which is the 1-2 position. This means that the methoxy (OCH3) group is attached to the position next to the hydroxyl group in a phenol molecule. The structure for o-methoxyphenol is: \[ HOC_{6}H_{4}-OCH_{3} \]
05

(e) p(t-tolyl)azophenol

To draw the structure of p(t-tolyl)azophenol, we need to know that "p" stands for the para position, which is the 1-4 position. Tolyl is a benzene ring with a methyl group attached. The azophenol part indicates a phenol ring with a nitrogen double bond (azo) linking to the t-tolyl group. The structure is: \[N=N-C_{6}H_{4}-OH \] ⟹ \[C_{7}H_{7}-N=N-C_{6}H_{4}-OH \]
06

(f) benzyl phenyl ether

The benzyl phenyl ether structure consists of two benzene rings. One has a phenyl ether substituent (O) and the other has a benzyl group (CH2) attached. The structure for benzyl phenyl ether is: \[ C_{6}H_{5}-O-CH_{2}-C_{6}H_{5} \]
07

(g) 3-(o-hydroxy phenyl pentanoic acid)

We need to draw a structure of an o-hydroxy phenyl group attached to a pentanoic acid (5 carbon chain) with a carboxyl group at one end. The structure is: \[ HO-C_{6}H_{4}-CH_{2}-CH_{2}-CH_{2}-CH_{2}-COOH \]
08

(h) 2-methoxy-1,4-naphthoquinone

To draw the structure for 2-methoxy-1,4-naphthoquinone, we need to know that naphthoquinone is a naphthalene ring with carbonyl groups at the 1 and 4 positions. The 2-methoxy part means that the methoxy group is attached to position 2. The structure for 2-methoxy-1,4-naphthoquinone is: \[ O=C-C_{10}H_{5}-C(=O)-OCH_{3} \]

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Most popular questions from this chapter

Phenol samples that have been allowed to stand in air always possess a pink or red color because of oxidation. Write a mechanism for the oxidation of phenol by oxygen that could lead to one or more products that might be expected to be colored.

(a) Hydroquinone is used in photographic developers to aid in the conversion of silver ion into free silver. What property of hydroquinone is being taken advantage of here? (b) p-Benzoquinone can be used to convert iodide ion into iodine. What property of the quinone is being taken advantage of here?

2, 4-Dichlorophenoxyacetic acid is the important weed-killer known as \(2,4-\mathrm{D}\). Outline the synthesis of this compound starting from benzene or toluene and acetic acid.

When phloroglucinol, \(1,3,5\) -trihydroxybenzene, is dissolved in concentrated \(\mathrm{HClO}_{4}\), its nmr spectrum shows two peaks of equal area at \(86.12\) and 8 4.15. Similar solutions of \(1,3,5-\) trimethoxybenzene and 1,3 , 5-triethoxybenzene- show similar nmr peaks. On dilution, the original compounds are recovered unchanged. Solutions of these compounds in \(\mathrm{D}_{2} \mathrm{SO}_{4}\) also show these peaks, but on standing the peaks gradually disappear. How do you account for these observations? What is formed in the acidic solutions? What would you expect to recover from the solution of \(1,3,5\) -trimethoxybenzene in \(\mathrm{D}_{2} \mathrm{SO}_{4} ?\)

Reduction of the carbony1 group of quercitin gives a substance that loses water readily to give a brilliant-violet compound, which, when treated with hydrochloric acid, is converted reversibly to a red salt. Consider possible ways that the reduction product might dehydrate to give a violet substance and show how addition of a proton to this substance could occur in such a way as to give a substantial color change:
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