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Okuyama & Maskill: Organic Chemistry


p. xxvii: The structure of digoxin should be as follows:


p. 19: In the molecular model of nitromethane, the bond between C (shaded black ball) and N (blue) should be a single line – not double.

p. 21: Problem 1.4 (d), "O, M" should be "O, Mg".

p. 24: The EPM of H2O in the margin is wrong: it should be replaced with the one on p. 11.

p. 83: The word "eclipsed" should be deleted from Figure 4.14.

p. 84: The chemical equations in Example 4.4 have erroneous arrows (the lower arrows should be longer than the upper ones).

p. 124: In the last group of structures (ch06mt124c in the website), the one in the middle is a wrong Lewis structure of p–methoxybenzoic acid, and a resonance arrow between the central structure and the one on the right is missing.  Replace the group with the one below:


p. 248: In Problem 11.6 (f), the subscript “3” is missing in the cationic substituent of Tamiful; “NH” should be “NH3” before the anion “H2PO4–”.

p. 245: The molecular model to the right of 2,6-dimethylspiro[3.3]heptane should be its mirror image. The correct image is shown below:


p. 272: The note “(Courtesy of the Royal Society of Chemistry)” in Problem 12.12 should be deleted.

p. 285: In Example 13.4, the reactants in part (b) should be cis-4-methylcyclohexyl bromide and sodium iodide.  The solution is as follows:

Iodide is a powerful nucleophile but only very weakly basic.  Consequently, the reaction proceeds by the SN2 mechanism to give trans-4-methylcyclohexyl iodide and sodium bromide which precipitates out of solution; this is an example of the so-called Finkelstein reaction.

p. 295: In Scheme 14.6, the name of the last compound should be “2–chloro–2–methylbutane” rather than “2–methyl–2–chlorobutane”.

p. 298: In Panel 14.2, an arrow to the right is missing from the end of the first line of the second (five-step) reaction.

p. 304: In Panel 14.6, the name of the first compound in the reaction scheme should be “D–mannose 2–trifluoromethanesulfonate 1,3,4,6–tetraacetate”.

p. 360: In Panel 16.2, line 3, Fe(II) should be Fe(III).

p. 370: In Problem 1.5, line 3, "water" should read "methanol".

p. 375: In Table 17.1 superscript "b" (corresponding to footnote b) is missing from the second structure in the column headed "Enol form".

p. 383: In Example 17.3, the name of the last compound in the chemical equation should be 3–hydroxy–2–methylpentanal.

p. 392: In the first of the three structures at the bottom of the page "1,3-pentanedione" should be replaced by "pentane-2,4-dione".

p. 497: In Scheme 22.8, the word under the arrow of the last step should be “hydration” rather than “hydrolysis”.

p. 535: In lines 3 and 2 from the bottom, and in the corresponding entries in the index on p. 620: “adenine” should read “adenosine” for ATP and ADP.

p. 536: in the first margin note, “nuleoside” should be “nucleoside”.