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Chapter 23: Problem 583

In which of the" following compounds would you expect intramolecular hy drogen bonding to occur; o-nitroaniline, o-cresol, o-hydroxybenzoic acid (salicylic acid), o-hydro-benzaldehyde (salicylaldehyde), o-fluorophenol, o-hydroxy- benzonitrile.

Short Answer

Expert verified
Intramolecular hydrogen bonding is expected to occur in the following compounds: o-nitroaniline, o-hydroxybenzoic acid (salicylic acid), o-hydro-benzaldehyde (salicylaldehyde), o-fluorophenol, and o-hydroxybenzonitrile. Only o-cresol does not exhibit intramolecular hydrogen bonding.

Step by step solution

01

Identify functional groups

First, let's identify the functional groups of each compound to identify potential hydrogen bond donors and acceptors. 1. o-nitroaniline: Amino (-NH2) and nitro (-NO2) groups. 2. o-cresol: Hydroxyl (-OH) and methyl (-CH3) groups. 3. o-hydroxybenzoic acid (salicylic acid): Carboxyl (-COOH) and hydroxyl (-OH) groups. 4. o-hydro-benzaldehyde (salicylaldehyde): Hydroxyl (-OH) and aldehyde (-CHO) groups. 5. o-fluorophenol: Hydroxyl (-OH) and fluorine (-F) groups. 6. o-hydroxybenzonitrile: Hydroxyl (-OH) and nitrile (-CN) groups.
02

Determine potential hydrogen bonding

Now we will determine which compounds have adjacent hydrogen bond donor and acceptor: 1. o-nitroaniline: Amino (-NH2) acts as a hydrogen bond donor, and nitro (-NO2) acts as a hydrogen bond acceptor. Adjacent, intramolecular hydrogen bonding is possible. 2. o-cresol: Hydroxyl (-OH) acts as a hydrogen bond donor, but there is no adjacent hydrogen bond acceptor. No intramolecular hydrogen bonding. 3. o-hydroxybenzoic acid (salicylic acid): Carboxyl (-COOH) can act as both a hydrogen bond donor and acceptor. The hydroxyl (-OH) group acts as a hydrogen bond donor. Intramolecular hydrogen bonding is possible. 4. o-hydro-benzaldehyde (salicylaldehyde): Hydroxyl (-OH) acts as a hydrogen bond donor, and the aldehyde's carbonyl oxygen can act as a hydrogen bond acceptor. Intramolecular hydrogen bonding is possible. 5. o-fluorophenol: Hydroxyl (-OH) acts as a hydrogen bond donor and fluorine (-F) acts as a hydrogen bond acceptor. Intramolecular hydrogen bonding is possible. 6. o-hydroxybenzonitrile: Hydroxyl (-OH) acts as a hydrogen bond donor, and nitrile (-CN) (specifically, the nitrogen atom) can act as a hydrogen bond acceptor. Intramolecular hydrogen bonding is possible.
03

Conclusion

Compounds which are expected to have intramolecular hydrogen bonding include: o-nitroaniline, o-hydroxybenzoic acid (salicylic acid), o-hydro-benzaldehyde (salicylaldehyde), o-fluorophenol, o-hydroxybenzonitrile. Out of the given compounds, only o-cresol does not exhibit intramolecular hydrogen bonding.

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Most popular questions from this chapter

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

Tropolone \(\left(\mathrm{I}, \mathrm{C}_{7} \mathrm{H}_{7} \mathrm{O}_{2}\right)\) has a flat molecule with all carbon-carbon bonds of the same length (1.40 A). The measured heat of combustion is \(20 \mathrm{kcal}\) lower than that calculated by the method of summing bond energies. Its dipole moment is \(3.71 \mathrm{D}\); that of 5-bromotropolone is \(2.07 \mathrm{D}\). Tropolone undergoes the Reimer-Tiemann reaction, couples with diazonium ions, and is nitrated by dilute nitric acid. It gives a green color with ferric chloride, and does not react with 2,4 -dinitrophenylhydrazine. Tropolone is both acidic \(\left(\mathrm{K}_{\mathrm{a}}=10^{-7}\right)\) and weakly basic, forming a hydrochloride in ether. (a) What class of compounds does tropolone resemble? Is it adequately represented by formula I? (b) Using both valence-bond and orbital structures, account for the properties of tropolone. (c) In what direction is the dipole moment of tropolone? Is this consistent with the structure you have proposed? (d) The infrared spectrum of tropolone shows a broad band at about \(3150 \mathrm{~cm}^{-1}\) that changes only slightly upon dilution. What does this tell you about the structure of tropolone?

4-n-Hexylresorcinol is used in certain antiseptics. Outline its preparation starting with resorcinol and any aliphatic reagents.

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 \(\mathrm{D}_{2} \mathrm{SO}_{4} ?\)

How do you account for the fact that, unlike most phenols, \(2,4-\) dinitrophenol and \(2,4,6\) -trinitrophenol are soluble in aqueous sodium bicarbonate?
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