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Chapter 10: Problem 157

From each pair of compounds, select the one that is more soluhle in water. (a) \(\mathrm{CH}_{2} \mathrm{Cl}_{2}\) or \(\mathrm{CH}_{2} \mathrm{OH}\) (b) \(\mathrm{CH}_{3} \mathrm{CXCH}_{3}\) or \(\mathrm{CH}_{3} \mathrm{CCH}_{3}\) (c) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{Cl}\) or \(\mathrm{NaCl}\) (d) CCCS \(\operatorname{cDT}\) CCC(O)CC

Short Answer

Expert verified
a) CH₂Cl₂ or CH₂OH b) CH₃CXCH₃ or CH₃CCH₃ c) CH₃CH₂Cl or NaCl d) CH₃CH₂CH₂SH or CH₃CH₂CH(OH)CH₂CH₃ Answer: a) CH₂OH b) CH₃CXCH₃ c) NaCl d) CH₃CH₂CH(OH)CH₂CH₃

Step by step solution

01

Identify the polar compounds

In this pair, we have \(\mathrm{CH}_{2}\mathrm{Cl}_{2}\) (dichloromethane) and \(\mathrm{CH}_{2}\mathrm{OH}\) (hydroxymethyl). The hydroxymethyl group contains an OH group, which is capable of forming hydrogen bonds with water molecules, whereas dichloromethane cannot form hydrogen bonds with water.
02

Determine the more soluble compound

Since hydrogen bonding interactions are crucial for solubility in water, \(\mathrm{CH}_{2}\mathrm{OH}\) will be more soluble in water compared to dichloromethane. (b) \(\mathrm{CH}_{3} \mathrm{CXCH}_{3}\) or \(\mathrm{CH}_{3} \mathrm{CCH}_{3}\)
03

Identify the functional groups

In this pair, both compounds have similar structures, with a single carbon atom bridging two methyl groups. In the first compound, the bridging carbon is bound to a halogen (X), while in the second compound, the bridging carbon has a triple bond to another carbon. Neither compound contains polar OH or NH groups that can strongly interact with water molecules.
04

Determine the more soluble compound

Both compounds have relatively low solubility in water due to their nonpolar structure. However, the halogen atom in \(\mathrm{CH}_{3}\mathrm{CXCH}_{3}\) introduces some polarizability, making it slightly more soluble in water compared to \(\mathrm{CH}_{3}\mathrm{CCH}_{3}\), which has a more nonpolar structure. (c) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{Cl}\) or \(\mathrm{NaCl}\)
05

Identify the polar compounds

In this pair, we have \(\mathrm{CH}_{3}\mathrm{CH}_{2}\mathrm{Cl}\) (chloroethane) and \(\mathrm{NaCl}\) (sodium chloride), an ionic compound. Sodium chloride readily dissolves in water because water molecules surround and solvate the Na+ and Cl- ions.
06

Determine the more soluble compound

Although chloroethane has a polar C-Cl bond, it does not form hydrogen bonds with water. On the other hand, sodium chloride is an ionic compound that dissociates in water, forming strong ion-dipole interactions with water molecules. Therefore, \(\mathrm{NaCl}\) is more soluble in water compared to chloroethane. (d)CCCS or CCC(O)CC
07

Identify the functional groups

The first compound (with the smile notation), \(\mathrm{CH}_{3}\mathrm{CH}_{2}\mathrm{CH}_{2}\mathrm{SH}\) (propanethiol), contains an SH group. The second compound, \(\mathrm{CH}_{3}\mathrm{CH}_{2}\mathrm{CH(OH)}\mathrm{CH}_{2}\mathrm{CH}_{3}\) (pentan-3-ol), contains an OH group and thus can form hydrogen bonds with water molecules.
08

Determine the more soluble compound

The presence of an OH group in pentan-3-ol increases its solubility in water due to hydrogen bonding with water molecules. Propanethiol only has an SH group, which is much less polar, resulting in lower solubility in water. Therefore, pentan-3-ol is more soluble in water compared to propanethiol.

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Most popular questions from this chapter

Proton transfer to the OH group to form an oxconium ion (add a proton) followed ly loss of \(\mathrm{H}_{2} \mathrm{O}\) (break a bond to give stable molecules or ions) gives a \(2^{\text {" carbocation }}\) intermediate. Miggration of a methyl group with its bonding pair of electrons from the adjacent carbon to the positively charged carbon gives a more stable \(3^{\text {" }}\) carbocation (1,2shift). Proton transfer from this intermediate to a base, here shown as \(\mathrm{H}_{2} \mathrm{O}\), gives the ohserved product (take a proton away). CC1=CC(C)=C(C)CC1 A \(2^{\mathrm{a}}\) carbocation internediate A \(9^{\circ}\) carbocation intermediate

Thiols are named in the same manner as aleohols, but the suffix e of the parent alkane is retained and thiol added. \- In compounds containing other functional groups of higher precedence, the presence of \(-\$ M\) is indicated by the prefix werapto.

Chrysamehemic acid occurs as a mixture of esters in flowers of the chryxanthemum (pyrethrum) family. Reduction of charysanthemaic acid to its alcohol (Section 17.6A) followed by conversion of the alcohol to its tosylate gives charysaathemyl tosylate. Solvolysis (Section 9.2) of the tosylate gives a mixture of artemesia and yomogi alcobok.

Make a new bond between a nucleophile and an electrophile. Reaction of the \(3^{7}\) carbocation (an electrophile) with bromide ion (a nucleophile) gives the alkyl halide. CC(C)(C)CBr CC(C)(Br)CC(C)(C)Br 2-Brome-2-rethylpropane (tert-Butyl bromide)

Treatment of alcolols with strong acidl leads to dehydration, which is elimination of water from adjacent rarbon atoms to give an alkene. \- Zaitsev's rule is folloved, that is, the predominant product is the most stable (usually the most highly substituted) alkene. The mechanism is the reverse of acid catalyzed hydration of an alkene.
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