ERRATA Organic Chemistry, 4th Edition, by G. Marc Loudon Date of this release: August 27, 2007

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1 ERRATA rganic Chemistry, 4th Edition, by G. Marc Loudon Date of this release: August 27, 2007 The only errata listed here are those that might affect understanding of the text. bvious errors such as simple misspellings are not included. Errors that have been corrected in the Second Printing are marked with an asterisk. Chapter 1 p. 23 (Courtesy of Stephanie Parker, Purdue) In the small-print section at the bottom of the page, the Study Guide Link reference should be 1.4, not 1.3. *p. 26 Chapter 4 In Figure 1.11(a), the perspective of the z-axis is poor; it should show across the front of the two left-hand lobes. p. 143 In the line above Eq. 4.29a, change cocentration to concentration. p. 189 In Eq. 5.58b, the 285 under the X = Br column should be 284 if it is to match the C Br bond energy in Table 5.3. This then requires the sum under the same column to be 20 kj mol 1. The overall conclusions, of course, are not changed. Chapter 6 *p. 205 In the paragraph beginning, The absence, the first word of the second line should be chiral, so that the sentence now reads: The absence of a plane of symmetry does not automatically mean that a molecule is chiral. (Thanks to Emily Hoehning, Purdue University) Chapter 7 p. 257 In Problem 7.2, the energy in kj/mol should be 7.4. p. 285 (Courtesy Danielle Carpenter, Purdue) The equation reference in the last line of the page should be to Eq. 7.37b. Chapter 9 *p. 371 In point 5, second line, substitute aprotic for apolar so that the line reads:...slower in protic solvents than in aprotic solvents... p. 380 (Courtesy Margaret Kunkel, Purdue) The equation should involve potassium iodide (K + I ) as the reactant and potassium bromide (K + Br ) as the product rather than the sodium salts, to match the discussion of the equation just above it. The potassium bromide selectively precipitates to drive the reaction. *p. 403 In Problem 9.51, last sentence of the seventh line, substitute the letter B for A so that the line reads: When compound B is...

2 Fourth Edition Text Errata, August 27, 2007, p. 2 Chapter 10 *p. 422 Chapter 11 *p. 475 Chapter 12 In the statement of Problem 10.15(a), first line, insert the word reaction before the word shown so that the line reads:...mechanism of the reaction shown... In the line of text just above Eq , insert the word as after the word acts so that the sentence reads:...acts as the ultimate oxidant. p. 498 In Eq. 12.2, the angstrom (Å) unit in the denominator of the first line should also have a cancellation slash. p. 510 (Courtesy of Brian Hong, Purdue) In Figure 12.7, the last structure on the second row has one arrow going in the wrong direction. It should be as follows: *p. 521 In Table 12.3, the exact mass of 81 Br should be , not Chapter 13 p. 554 In Problem 13.8(a), the structure has too many methyl groups. It should be *p. 562 *p. 566 *p. 567 (CH 3 ) 3 C C(CH 3 ) 2 In the figure caption near the end of the 4th line, in the phrase bring the a proton the a should be italicized because it is a proton label. In the second sentence of the caption for Figure 13.10, replace the word shown with the word show so that the sentence reads: The insets show the resonances... In Figure 13.11, substitute H b for H c in the caption at the far right so that it reads: Cl chemical shift of H b δ 4.54 p. 571 (Courtesy of Thomas Shum, Purdue) At the start of the eighth line up from the bottom, the chemical shift should be δ 0.9, not 0.9 Hz. *p. 603 In Figure P13.44, the integral of the resonance that disappears on D 2 shake should be 1H, not 2H.

3 Fourth Edition Text Errata, August 27, 2007, p. 3 Chapter 14 p. 612 In the display near the top of the page, a more inclusive range for vinylic protons is δ , and a more inclusive range for allylic protons is δ *p. 624 *p. 624 Chapter 15 The callout to Study Guide Link 14.2 should be checked ( ). In the second sentence of the last paragraph, delete the word of after reagents so that the sentence reads:...which are reagents with the general structure... p. 638 (Courtesy of Brian Hong, Purdue) In Table 15.1, the last structure is missing a hydrogen. It should be CH 3 CH C CHCH 3. p. 655 (Courtesy of Tim D Auria, Cornell University) In Eq b, a double bond is missing in the product. The product should be *p. 662 In the second line of text following Eq , add the word the before 1,4- addition product so that the line reads:...eq shows that the 1,4-addition product is more stable... *p. 668 *p. 675 *p. 682 *p. 690 Chapter 16 *p. 718 Chapter 17 Reword Guideline 4 at the bottom of the page to read: Structures in which electron deficiency is assigned to more electropositive atoms and unshared pairs to more electronegative atoms are more important. In the 5th line of text in Section B, the second occurrence of the word bond should be plural, so that the line reads: carbon-carbon bond: single bonds and double bonds. In the 4th line up from the problem set, the change the word reactions to reaction so that the sentence reads: However, the reaction conditions for these... The last equation in Figure P15.62 should be numbered as (g), not (h). In Problem 16.20(a), second line, the equation reference should be changed to Eq , so that the line reads: in Eq ) in the presence... p. 773 (Courtesy of Christina Chung, Purdue) In the first line of the left column, the figure reference should be to P17.41.

4 Fourth Edition Text Errata, August 27, 2007, p. 4 Chapter 18 p. 780 In the second-to-last line of the caption of Figure 18.1, the word collinear is misspelled. *p. 789 *p. 791 In the display (both structures), the name of the NH 3 ligand should be ammine, not ammino. Thus, the names should be cis-diamminedichloroplatinum(ii) and hexamminecobalt(iii) ion. (See also the correction for p. 791.) In Table 18.1, the name of the H 3 N ligand is ammine, not ammino. The -o suffix is used for negatively charged ligands only. p. 799 In Eq , the directions of the double arrows should be reversed: PPh 3 ligand association *p. 816 In Eq delete the dot that follows the Br. *p. 819 *p. 822 *p. 823 Chapter 20 *p. 920 *p. 923 *p. 931 Chapter 21 *p. 942 In the 8th line of text, first word, change undergoing to undergo. In Eq , the first by-product (CH 3 ) 3 SnCl is incorrect; this should be changed to (CH 3 CH 2 CH 2 CH 2 ) 3 SnCl. In Problem 18.33, the first reactant listed should be ethynyltrimethylstannane, not ethnyltributylstannane. The starting material in Problem 20.15(c) should be p-toluenesulfonic acid; the p- was omitted. In Problem 20.20(b), change the name of the product to 3-phenylpropanoic acid, so that the problem reads: (b) benzoic acid into 3-phenylpropanoic acid In reaction (e) of Figure P20.50, the reagent over the arrow should be H 2, not HCI. In the first sentence of Problem 21.5, change the word ethyl to the word methyl, so that the sentence reads: Pentanoic acid and methyl butyrate are constitutional isomers. (Courtesy of Pinn Suppatkul, Purdue) In the first set of structures, the structure of 2-butanone is wrong. It should be *p. 961 In the third line of the paragraph beginning, Now consider the leaving-group

5 Fourth Edition Text Errata, August 27, 2007, p. 5 *p. 961 *p. 972 effect..., add the word a before the word decrease, so that the line reads: is reflected in a decrease... In the final paragraph, which begins, We have learned... omit the word to, so that the sentence reads: We have learned the following two... In the fourth line of the page, add the word a after the word thus, so that the line reads: actually a rather weak base and thus a fairly good leaving group. p. 972 In Eq e, the nitrogen of the first structure is missing an R group. The structure should be Chapter 22 *p In Eq a, there should be a coefficient of 3 with the Br 2 (to read 3Br 2 ) on the left side of the equation. p This is not an error but a further explanation of what is happening in Eq This is in effect the interchange of the Br of an acid bromide and the H of a carboxylic acid. The mechanism is essentially the one shown in Study Guide Link 20.6, p. 708, of the Study Guide & Solutions Manual if you substitute the acid bromide for thionyl chloride and Br for Cl. Thus, the first step of the mechanism would be Chapter 23 *p We leave it to you to complete the mechanism. In Eq , the counter-ion in the diazonium salt (the second structure) should be HS 4, not Cl, because sulfuric acid, not HCl, is used as the acid in its preparation. p In the second line of the three-line introduction to Sec , the cross-reference should be to Sec D, not to Sec. 23.7D. *p The H 2 S 4 over the last arrow in Eq b should have no negative charge.

6 Fourth Edition Text Errata, August 27, 2007, p. 6 Chapter 24 p In the first line of text, add planar at the end so that the line reads, trigonal planar. p (Courtesy Jagruti Patel, Purdue) In Eq c at the top of the page, the Nuc in the first structure should have a negative charge. p The fourth line of text from the bottom, beginning These resonance structures also show should begin a new paragraph. *p Chapter 25 In Problem 24.61(c), change the Figure reference to Fig. P24.61, so that the problem reads: (c) The reaction given in Fig. P24.61 takes place... *p In the 3rd line of the caption for Fig. 25.1, change the first symbol ψ 1 * to ψ 2 *. Chapter 26 *p *p In the 2nd line of Problem 26.9, change Eq to Eq. 26.7a, so that the sentence reads: Use this condition, along with Eq. 26.5, to derive Eq. 26.7a, the formula for... In the 6th line below display add the word of before the word amino, so that the sentence reads: We would expect the AQC derivatives of amino acids... p In the third panel of Figure (the middle panel on the left side), the colored leaving group should be Pep C NH 2, not Pep N NH 2. *p Chapter 27 *p *p In the first line of Section B, change a essential to an essential. In the line below the first display, which begins, Contrast the reaction..., the word hemiacetal is misspelled. In Eq the aldehyde carbonyl should be black and the formic acid carbonyl should be colored. (The colored carbonyl is bold-faced in the following revised structures.)

7 Fourth Edition Text Errata, August 27, 2007, p. 7 H R CH CH + HC R!-hydroxy aldehyde (not oxidized further) H 5 I 6 R C H + H C H formic acid p In the fifth line from the bottom of the second full paragraph, the three processes mentioned are correct, but should be listed in the order cyanohydrin formation, reduction, and hydrolysis to correspond to the order in Eqs and *p In Problem 27.34(f) a base catalyst such as pyridine should be included, although the reaction would probably proceed more slowly without it. Appendix IV *p. A-8 The chemical-shift range for carbons adjacent to a benzene ring (benzylic carbons, the third entry) should be ppm. Appendix V p. A-9 (Courtesy Phillip Barr, U. Tennessee) Under B. Synthesis of Alkenes, Reaction 4 should conclude with the words, when used with internal alkynes; 14.6B). Appendix VII p. A-14 In the second-to-last entry, under benzylic alkyl group, the AR in the third column should be Ar. (The R should not be capitalized.) Index p. I-4 (Courtesy of John Bartmess, U. Tennessee) In the second column under Alkynes, preparation, by E2 reactions of vinylic halides, the page reference is missing. It should be p p. I-22 The page reference in the third column under Membranes of cells, structure, should be *******

ERRATA. p. 2 In the second line from the bottom, the expression should be , not

ERRATA. p. 2 In the second line from the bottom, the expression should be , not ERRATA Study Guide and Solutions Manual, Fifth Edition by Marc Loudon and Joseph G. Stowell to accompany Organic Chemistry, 5th Edition, by Marc Loudon Date of this release: May 2, 2011 Items marked with