SOLUTIONS TO TEXT PROBLEMS 24.(b) A benzyl group(C., CH2) is ortho to the phenolic hydroxyl group in o-benzylphenol. OH CH2C.Hs (c)Naphthalene is numbered as shown. 3-Nitro-I-naphth has a hydroxyl group at C-1 and a nitro group

22.2 N,N-Dimethylcycloheptylamine may also be named as a dimethyl derivative of cycloheptanamine. -N(CH3)2 N,N-Dimethylcycloheptanamine 22.3 Three substituents are attached to the nitrogen atom; the amine is tertiary. In alphabetical order, the s substituents present on the aniline nucleus are ethyl, isopropyl, and methyl. Their positions are

20.1 () Carboxylic aci id anhydrides bear two acyl groups on oxygen, as in RCOCR. They are named as derivatives of carboxylic acids. Q CH:CH2CHCOH CH,CH,CHCOCCHCH_CH3 C6H C. C. 2-Phenylbutanoic acid 2-Phenylbutanoic anhydride (c) Butyl 2-phenylbutanoate is the butyl ester of 2-phenylbutanoic acid. CH,CH,CHCOCH,CH,CH2CH

ENOLS AND ENOLATES SOLUTIONS TO TEXT PROBLEMS 18.1(b) There are no a-hydrogen- atoms in2,2-dimethylpropa, because the a-carbon- atom bears three methyl groups

Oxirane 2-(Chloromethyl)oxirane This compound is more commonly known as epichlorohydrin. (c)Epoxides may be named by adding the prefix epoxy to the IUPAC name of a parent compound specifying by number both atoms to which the oxygen is attached

SOLUTIONS TO TEXT PROBLEMS 14.1 () Magnesium bears a cyclohexyl substituent and a chlorine. Chlorine is named as an anion. The compound is cyclohexylmagnesium chloride. 14.2 (b) The alkyl bromide precursor to sec-butyllithiur must be sec-butyl bromide

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

10.1 As noted in the sample solution to part(a), a pair of electrons is moved from the double bond toward the positively charged carbon

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 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: