McGraw-Hill Higher Education A Division of The McGrawp-Hill Companies ORGANIC CHEMISTRY, FOURTH EDITION Copyright 2000, 1996, 1992, 1987 by The McGraw-Hill Companies, Inc. All rights reserved. Printed in the United States of America. Except as permitted under the United States Copyright Act of 1976, no part of this publication may be reproduced or distributed in any form or by any means, or stored in a data base or retrieva

1.1 The element carbon has atomic number 6, and so it has a total of six electrons. Two of these elec- tr rons are in the Is level. The four electrons in the 2s and 2p levels (the valence shell) are the valence electrons. Carbon has four valence electrons 1.2 Electron configurations of elements are derived by applying the following principles:

SOLUTIONS TO TEXT PROBLEMS 3.1 (b) The sawhorse formula contains four carbon atoms in an unbranched chain. The compound is butane, CH:CH,CH, CH3 CH3 HH H-H CH ()Rewrite the structure to show its constitution. The compound is

SOLUTIONS TO TEXT PROBLEMS 5.1 (b) Writing the structure in more detail, we see that the longest continuous chain contains four carbon atoms

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

SOLUTIONS TO TEXT PROBLEMS 9.1 The reaction is an acid-base process; water is the proton donor. Two separate proton-transfer steps are involved

assuming that there is no resonance stabilization in 1, 3,5-cycloheptatriene, we predict that its heat of hydrogenation will be three times that of cycloheptene or 330/mol (78.9 kcal/mol)

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

SOLUTIONS TO TEXT PROBLEMS 15.1 The two primary alcohols, 1-butanol and 2-methyl-1-propanol, can be prepared by hydrogenation of the corresponding aldehydes

SOLUTIONS TO TEXT PROBLEMS functions at both ends. Pentanedial is an acceptable IUPAC name for this compound.hyde 17.1 (b) The longest continuous chain in glutaraldehyd has five carbons and terminates in ald