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Chapter 30: Problem 697

Which of the following compounds would exhibit detergent properties? (a) \(\mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{10} \mathrm{CH}_{2} \mathrm{~N}^{+}\left(\mathrm{CH}_{3}\right)_{3} \mathrm{Cl}^{-}\) (b) \(\mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{10} \mathrm{CH}_{2} \mathrm{COOCH}_{3}\) (c) \(\mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{10} \mathrm{CH}_{2} \mathrm{SO}^{-}{ }_{3} \mathrm{Na}^{+}\)

Short Answer

Expert verified
The compounds (a) \(\mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{10} \mathrm{CH}_{2}\mathrm{~N}^{+}\left(\mathrm{CH}_{3}\right)_{3} \mathrm{Cl}^{-}\) and (c) \(\mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{10} \mathrm{CH}_{2}\mathrm{SO}^{-}{ }_{3} \mathrm{Na}^{+}\) exhibit detergent properties, as they have both hydrophilic and hydrophobic parts.

Step by step solution

01

Compound (a)

The compound (a) has a long hydrocarbon chain \(\mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{10} \mathrm{CH}_{2}\), which is hydrophobic. The end of the compound has a charged group \(\mathrm{~N}^{+}\left(\mathrm{CH}_{3}\right)_{3} \mathrm{Cl}^{-}\), which is hydrophilic.
02

Compound (b)

The compound (b) also has a long hydrocarbon chain \(\mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{10} \mathrm{CH}_{2}\), which is hydrophobic. The end of the compound has an ester group \(\mathrm{COOCH}_{3}\), which is not charged and not hydrophilic.
03

Compound (c)

The compound (c) has a long hydrocarbon chain \(\mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{10} \mathrm{CH}_{2}\), which is hydrophobic. The end of the compound has a charged group \(\mathrm{SO}^{-}{ }_{3} \mathrm{Na}^{+}\), which is hydrophilic. #Step 2: Evaluate detergent properties# We are now going to evaluate the detergent properties based on the presence of both hydrophilic and hydrophobic parts in each compound.
04

Evaluate Compound (a)

Compound (a) has a hydrophobic part, the long hydrocarbon chain, and a hydrophilic part, the charged group \(\mathrm{~N}^{+}\left(\mathrm{CH}_{3}\right)_{3} \mathrm{Cl}^{-}\). Hence, this compound can exhibit detergent properties.
05

Evaluate Compound (b)

Compound (b) has a hydrophobic part, the long hydrocarbon chain, but the end group is not hydrophilic (it is an ester group \(\mathrm{COOCH}_{3}\)). This compound will not exhibit detergent properties because it lacks a hydrophilic part.
06

Evaluate Compound (c)

Compound (c) has a hydrophobic part, the long hydrocarbon chain, and a hydrophilic part, the charged group \(\mathrm{SO}^{-}{ }_{3} \mathrm{Na}^{+}\). This compound can also exhibit detergent properties. #Step 3: Determine the answer# Based on our evaluations, compounds (a) and (c) exhibit detergent properties. So, the answer is (a) and (c).

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Most popular questions from this chapter

Spermaceti (a wax from the head of the sperm whale) resembles high-molecular weight hydrocarbons in physical properties and inertness toward \(\mathrm{Br}_{2} / \mathrm{CCl}_{4}\) and \(\mathrm{KMnO}_{4} ;\) on qualitative analysis it gives positive tests only for carbon and hydrogen. However, its infrared spectrum shows the presence of an ester group, and quantitative analysis gives the empirical formula \(\mathrm{C}_{16} \mathrm{H}_{32} \mathrm{O}\) A solution of the wax and \(\mathrm{KOH}\) in ethanol is refluxed for a long time. Titration of an aliquot shows that one equivalent of base has been consumed for every \(475 \pm 10\) grams of wax. Water and ether are added to the cooled reaction mixture, and the aqueous and ethereal layers are separated. Acidification of the aqueous layer yields a solid \(\mathrm{A}\), m.p. \(62-3^{\circ}\), neutralization equivalent \(260 \pm 5\). Evaporation of the ether layer yields a solid B, m.p. \(48-9^{\circ}\). Reduction by LiAlHi \(_{4}\) of either spermaceti or A gives \(B\) as the only product. B is normal alcohol. What is the structure of spermaceti?

In 1904, Franz Knoop outlined a scheme for the biological oxidation of fatty acids that was shown \(-50\) years later \(-\) to be correct. In his key experiments, he fed rabbits fatty acids of formula \(\mathrm{C}_{6} \mathrm{H}_{5}\left(\mathrm{CH}_{2}\right)_{\mathrm{n}}\) COOH. When the side chain \((\mathrm{n}+1)\) contained an even number of carbons, a derivative of phenylacetic acid, \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{COOH}\), was excreted in the urine; an odd number, and a derivative of benzoic acid was excreted. What general hypothesis can you formulate from these results?

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