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Chapter 27: Problem 80

Explain the important distinctions between each pair of terms: (a) base and nucleophile; (b) \(\alpha\) carbon and \(\beta\) carbon; (c) polar protic solvent and polar aprotic solvent; (d) carbocation and radical.

Short Answer

Expert verified
In brief, a base can accept a proton while a nucleophile donates a pair of electrons. An \(\alpha\)-carbon is the first carbon attached directly to a functional group and \(\beta\)-carbon is the second one away from it. Polar protic solvents can form hydrogen bonds, while polar aprotic solvents cannot. Carbocation has a positively charged carbon atom whereas a radical has one or more unpaired electrons.

Step by step solution

01

Base and Nucleophile

A base is a molecule that can accept a proton, it can grab a hydrogen atom from another molecule. In contrast, a nucleophile signifies a molecule that can donate a pair of electrons to another molecule, hence can attack other molecules, particularly electrophiles.
02

\(\alpha\) carbon and \(\beta\) carbon

\(\alpha\)-carbon signifies the first carbon attached directly to a functional group. \(\beta\)-carbon, however, is the second carbon atom away from the functional group.
03

Polar Protic Solvent and Polar Aprotic Solvent

Polar protic solvents are substances that have at least one replaceable hydrogen atom and can form hydrogen bonds. For example, water (\(H_2O\)), alcohol (\(ROH\)), etc. Conversely, polar aprotic solvents have their hydrogen atom connected to atoms other than carbon or hydrogen making them incapable of forming hydrogen bonds. These solvents include dichloromethane (\(CH_2Cl_2\)) or acetone (\(C_3H_6O\)).
04

Carbocation and Radical

A carbocation refers to a molecule that includes a positively charged carbon atom. It occurs when a carbon atom loses one of its bonding electron pairs, leaving it with only three bonds and a positive charge. On the other hand, a radical, also known as a free radical, refers to a molecule having one or more unpaired electrons. Radicals are often very reactive as they seek to either donate or accept an electron to achieve a stable electron configuration.

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Most popular questions from this chapter

Indicate the principal product(s) you would expect in (a) treating \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}=\mathrm{CH}_{2}\) with dilute \(\mathrm{H}_{2} \mathrm{SO}_{4}(\mathrm{aq})\) (b) exposing a mixture of chlorine and propane gases to ultraviolet light; (c) heating a mixture of isopropyl alcohol and benzoic acid; (d) oxidizing sec-butyl alcohol with \(\mathrm{Cr}_{2} \mathrm{O}_{7}^{2-}\) in acidic solution.

Predict the major organic product obtained in each of the following reactions. Assume that [O] represents \(\mathrm{Na}_{2} \mathrm{Cr}_{2} \mathrm{O}_{7}\) in \(\mathrm{H}_{2} \mathrm{SO}_{4}\) (a) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHCH}_{2} \mathrm{OH}+\mathrm{HBr} \longrightarrow\) (b) \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{COH}+\mathrm{K} \longrightarrow\) (c) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHOH} \stackrel{[\mathrm{O}]}{\longrightarrow}\) (d) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}+\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{I} \longrightarrow\)

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Describe what is meant by each of the following reaction types, and illustrate with an example from the text: (a) dehydration; (b) hydrolysis; (c) solvolysis; (d) hydration of an alkene.

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