SOLUTIONS TO TEXT PROBLEMS 7.1 (c)Carbon-2 is a stereogenic center in 1-bromo-2-methylbutane, as it has four different substituents: H, CH, CH,CH2, and BrCH2. H BrCH2-C-CH2CH, CH3 (d) There are no stereogenic centers in2-romo-2- me. Br CH:-C-CH,CH3 CH, 7.(b) Carbon-2 is a stereogenic center in 1, 1, 2-trimethylcyclobutane

4.1 There are four C. H, alkyl groups, and so there are four C. H, CI alkyl chlorides. Each may be named by both the functional class and substitutive methods. The functional class name uses the name of the alkyl group followed by the halide as a second word. The substitutive name modifies the name of the corresponding alkane to show the location of the halogen atom

SOLUTIONS TO TEXT PROBLEMS 6.1 Catalytic hydrogenation converts an alkene to an alkane having the same carbon skeleton. Since 2-methylbutane is the product of hydrogenation, all three alkenes must have a four-carbon chain with a one-carbon branch. The three alkenes are therefore:

SOLUTIONS TO TEXT PROBLEMS 8.1 Identify the nucleophilic anion in each reactant. The nucleophilic anion replaces bromine as a sub- stituent on carbon. (b) Potassium ethoxide serves as a source of the nucleophilic anion CH,CH,. CH,CH,: CH, Br: CH3CH2OCH3 + Br: Ethoxide ion Methyl bromide Ethyl methyl ether Bromide ion

SOLUTIONS TO TEXT PROBLEMS 13.1 The field strength of an NMR spectrometer magnet and the frequency of electromagnetic radia he Ire tion used to observe an NMR spectrum are directly proportional. Thus, the ratio 4.7 T/200 MHz is the same as 1.41/60 MHz. The magnetic field strength of a 60-MHz NMR spectrometer is

The positive charge is shared equally by the three carbons indicated. Thus the two carbons ortho to the sp. e sp-hybridized carbon and the one para to it each bear one third of a positive charge (+0.33). None of the other carbons is charged. The resonance picture and the simple MO treatment agree with respect to the distribution of charge in cyclohexadienyl cation

Look at the drawing from a perspective that permits you to see the carbon chain oriented ver tically with the aldehyde at the top and the Ch,oh at the bottom. Both groups should point away from you. When examined from this perspective, the hydrogen is to the left and the hydroxyl to the right with both pointing toward you

Chlorotoluene Benzyl chloride Of this group only benzyl chloride is not an aryl halide; its halogen is not attached to the aromatic ring but to an sp-hybridized carbon. Benzyl chloride has the weakest carbon-halogen bond, its measured carbon-chlorine bond dissociation energy being only 293 kJ/mol (70 kcal/mol). Homolytic cleavage of this bond produces a resonance-stabilized benzyl radical

SOLUTIONS TO TEXT PROBLEMS 21.1 Ethyl benz emuale cannor undergo the Claisen condensation, beca use it has no protons on its a- t has ho ts a-carbon on its a- atom and so cannot form an enolate Ethyl pentanoate and ethyl phenylacetate can undergo the Claisen condensation

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