Arrow heads (pp. 23–34)
The curved lines should not have arrow heads at the beginning or end. Thanks to Tadashi Okuyama for reporting this error.
The nucleophilic C is on the bottom of both starting material and product, not on the right. Thanks to Tadashi Okuyama for reporting this error.
CAN is an abbreviation for Ce(NH4)2(NO3)6, not Ce(NH3)2(NO3)6. Thanks to Shen Muzhi for reporting this error.
In question 4c, a C atom is missing from the product. The correct figure is below. Thanks to Kaitlyn Corazzata for reporting this error.
The order of energy of the different carbonyl compounds is stated backward in the text. The correct order is RCOCl (highest in energy) > RCO2COR > RCHO > R2CO > RCO2R > RCONR2 (lowest in energy). The associated figure is correct. Thanks to Tom Dawson for reporting this error.
In the second step of the mechanism of the serine proteases, the electron-flow arrow showing the formation of the new N–H bond should originate at the cleaving C–N bond, as shown below. Thanks to Alex Lin for reporting this error.
In the last line of p. 98, "carbanionic" should be "organolithium". Thanks to Tadashi Okuyama for reporting this error.
In question gg, the product should be trans, not cis. Thanks to an unnamed reader for reporting this error.
The mechanism for the reaction of a primary amine with HNO2 that is shown and discussed in the text is probably incorrect. The initial protonation of HNO2 should occur at the O doubly bonded to N, not the O singly bound to N, as shown here.
The reaction in Problem 3.17 is a Strecker reaction, not a Stetter reaction. Thanks to Michael W. Fennie for reporting this error.
The product in problem (i) is missing an O atom. The correct equation is below. Thanks to Feiyu Zhou for reporting this error.
On p. 206, in the fourth line of text after the first figure, the text describes the 3-membered ring intermediate in Mechanism 1 as a cyclopropane, but it is better described as a cyclopropanone. Thanks to Tadashi Okuyama for reporting this error.
In the first figure on page 237, the two PhN atom labels in the products should be X. Thanks to Tadashi Okuyama for reporting this error.
The bottom right structure in the figure in the middle of the page should show a single bond, not a double bond, to H. Thanks to Tadashi Okuyama for reporting this error.
The second sentence in section 4.4.1 asserts that the position of the equilibrium in sigmatropic rearrangements depends on both the thermodynamic and kinetic stabilities of the starting material and product. In fact, only the thermodynamic stabilities are relevant. Thanks to Tadashi Okuyama for reporting this error.
In the second paragraph on page 254, the seventh sentence should read as follows:
In the last figure on p. 255 and the first figure on p. 256, the two R groups on the right side of the transition-state structure should be R3 and R4, not R1 and R2. Thanks to You-Chen Lin for reporting this error.
In the last figure on p. 258, the reagent above the arrow should be CH3C(OEt)3. Thanks to Adam Kang for reporting this error.
The third line of graphics on p. 274 should be below the paragraph beginning with the number 5, not above it. Thanks to Tadashi Okuyama for reporting this error.
In question (i), the first structure should have only one double bond in the ring, as shown below. Thanks to You-Chen Lin for reporting this error.
In question (u), the reagent above the arrow should be (COCl)2, not COCl2. Thanks to Tim Chyrklund for reporting this error.
The order of energy of alkyl radicals is stated backward in the text. The correct order of energy is 3° (lowest in energy) < 2° < 1° < ·CH3 (highest in energy). Thanks to Michael W. Fennie for reporting this error.
A plus sign is missing from the leftmost N atom in the first structure in the second line of structures on p. 285. Thanks to Shuqi Ye for reporting this error.
In the first figure, the two resonance arrows on the right should be replaced with regular reaction arrows.
In the second figure, the O atom of the ketyl radical (second figure) should bear six unshared electrons, not five. The correct figure is below. Thanks to Michael W. Fennie for reporting this error.
The R1 and R2 groups on the right side of the transition state structure in the first line of graphics on p. 299 should be R3 and R4. Thanks to Tadashi Okuyama for reporting this error.
In the second figure, the reaction of the Zr compound in the center with Cu–X to the lower right should be labelled as a transmetallation (c), not as an insertion (b). Thanks to You-Chen Lin for reporting this error.
In the last paragraph of p. 370, I describe Me2Cu− as a 16-electron species and its coordination complex with an alkene as an 18-electron complex. As I have drawn them in the corresponding figure, they are 14- and 16-electron species, respectively. However, if another ligand is coordinated to Cu, as seems likely, then they would be 16- and 18-electron species, respectively. Thanks to Tianbo Xie for reporting this error.
In the second paragraph on page 374, line 3, Cp2TiCl2 should be replaced with Ti(O-i-Pr)4. Thanks to Tadashi Okuyama for reporting this error.
The Pd atom in LnPdX−, the compound on the bottom left in the first figure, is in the oxidation state (0), not (II). Thanks to You-Chen Lin for reporting this error.
In the last equation on p. 390, the reagent on the arrow should be (Ph3P)4Pd, not (Ph3)4Pd. Thanks to Tadashi Okuyama for reporting this error.
In the last equation on p. 401, the n-Bu group should be a Ph group. Thanks to Tadashi Okuyama for reporting this error.
Structure 6 in question 3(d) should be a ketone, not an alcohol. The correct figure is below. Thanks to Michael W. Fennie for reporting this error.
The text correctly describes the more acidic compound, but the less acidic compound is circled. Thanks to Terence Ma for reporting this error.
The text incorrectly describes the first step of the mechanism as a two-electron electrocyclic ring opening. It is actually a four-electron electrocyclic ring opening. Thanks to Keyi Liang for reporting this error.
− Two one-electron oxidations occur in this reaction. First, the β-keto ester forms a Mn(III) enolate, and the Mn–O bond undergoes homolytic cleavage to give Mn(II) and an O radical. A series of radical cyclizations takes place to generate a tetracyclic compound with a 3° alkyl radical. This compound transfers one electron to Cu(II) to give a carbocation, which undergoes C–H bond fragmentation to give the observed product.
Thanks to Maithili Pokle for reporting this omission.
BrMg+ should be ClMg+. Thanks to You-Chen Lin for reporting this error.
The Pd atoms in the two allyl–Pd complexes are in the oxidation state (II), not (0). Thanks to You-Chen Lin for reporting this error.
Position of nucleophilic C (p. 44)
Formula of CAN (p. 47)
Missing C (p. 56)
Order of energy of carbonyl compounds backward (p. 72)
Misplaced electron-flow arrow (p. 88)
Description of product (p. 98)
Stereochemistry of product (p. 130)
Mechanism of diazonium ion formation from amine and HNO2 (p. 161)
Misnamed reaction (p. 169)
Missing O (p. 187)
Description of 3-membered ring intermediate (p. 206)
PhN → X (p. 237)
Double bond to H (p. 238)
Relationship of equilibrium constant to kinetic and thermodynamic stabilities (p. 247)
Whether H(1s) or ψ1 is lower in energy (p. 254)
It is clear that the H(1s) orbital is lower in energy than the antibonding orbital ψ1, but it is not clear whether H(1s) or ψ0 [not ψ1] is lower in energy.
Thanks to You-Chen Lin for reporting this error.
Wrong R group numbers (p. 255–256)
Missing C in formula (p. 258)
Position of third line of graphics (p. 274)
Too many π bonds (p. 276)
Wrong reagent (p. 279)
Order of energy of alkyl radicals backward (p. 284)
Missing plus sign (p. 285)
Wrong kind of arrows; O electron count in ketyl radical (p. 290)
Numbering of R groups in transition state structure (p. 299)
Reaction of Zr compound with CuX (p. 360)
Electron count of Cu species (p. 370)
Wrong Ti compound (p. 374)
Oxidation state of [LnPdX]− (p. 386)
Missing P (p. 390)
n-Bu should be Ph (p. 401)
Ketone, not alcohol (p. 417)
Less acidic compound circled (answer key Chap. 1 end-of-chapter question 2g)
Number of electrons in electrocyclic reaction (answer key Chap. 4 end-of-chapter question 6v)
Omitted answer (answer key Chap. 5 end-of-chapter question 3ee)
Cl not Br (answer key Chap. 6 in-chapter question 6.11)
Oxidation state of allyl–Pd complexes (answer key Chap. 6 end-of-chapter question 1b)