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1 CAPTER R R R R Solutions ,5-dibromo-2-methylhexan-2-ol (2S,3R)-2,3,4-trimethylpentan-1-ol 2,2,5,5-tetramethylcyclopentanol d) 2,6-diethylphenol e) (S)-2,2,4,4-tetramethylcyclohexanol Nonyl mandelate has a longer alkyl chain than octyl mandelate and is therefore more effective at penetrating cell membranes, rendering it a more potent agent. Nonyl mandelate has a shorter alkyl chain than decyl mandelate and is therefore more watersoluble, enabling it to be transported through aqueous media and to reach its target destination more effectively.
2 280 CAPTER Na Na Na Na Li Li d) Na Na F F The electron-withdrawing effects of the fluorine atoms stabilize the conjugate base. The conjugate base of a primary alcohol will be more easily solvated than the conjugate base of a tertiary alcohol. The electron-withdrawing effects of the chlorine atoms stabilize the conjugate base. d) The conjugate base is more highly stabilized by resonance, with the negative charge spread over two oxygen atoms, rather than just one oxygen atom.
3 CAPTER e) The conjugate base is stabilized by resonance nitrophenol is expected to be more acidic (lower pk a ) because the conjugate base has a resonance structure in which the negative charge is spread onto an oxygen atom of the nitro group, shown below. In contrast, 3-nitrophenol does not have such a resonance structure: N N Na dilute 2 S 4 d) e) 1) B 3 TF 2) 2 2, Na 1) g(a 2, 2 2) NaB 4 1) B 3 TF f) 2) 2 2, Na
4 282 CAPTER ) B 3 TF 2) 2 2, Na 1) g(a 2, 2 2) NaB 4 dilute 2 S (+2) (+2). The starting material is neither oxidized nor reduced. (+1) (+3). The starting material is oxidized. (+3) (-1). The starting material is reduced. d) (+3) (+3). The starting material is neither oxidized nor reduced. e) (0) (+2). The starting material is oxidized. f) (+2) (+3). The starting material is oxidized ne carbon atom is reduced from an oxidation state of 0 to an oxidation state of -1, while the other carbon atom is oxidized from an oxidation state of 0 to an oxidation state of +1. verall, the starting material does not undergo a net change in oxidation state and is, therefore, neither reduced nor oxidized ne carbon atom is reduced from an oxidation state of 0 to an oxidation state of -2, while the other carbon atom is oxidized from an oxidation state of 0 to an oxidation state of +2. verall, the starting material does not undergo a net change in oxidation state and is, therefore, neither reduced nor oxidized Al
5 CAPTER Al Me B d) Al e) Al Al f) Me Me Me Me B
6 284 CAPTER Al Al ) MeMg 2) 2 1) PrMg 2) 2 1) MeMg 2) 2 1) PrMg 2) 2 1) PrMg 2) 2
7 CAPTER d) 1) EtMg 2) 2 1) 2) 2 Mg e) 1) MeMg 2) 2 1) EtMg 2) 2 1) BuMg 2) 2 f) 1) MeMg 2) 2 1) 2) 2 Mg Each of the following two compounds can be prepared from the reaction between a Grignard reagent and an ester, because each of these compounds has two identical groups connected to the position: Me Me The other four compounds from Problem do not contain two identical groups connected to the position, and cannot be prepared from the reaction between an ester and a Grignard reagent.
8 286 CAPTER Each of the following three compounds can be prepared from the reaction between a hydride reducing agent (NaB 4 or LA) and a ketone or aldehyde, because each of these compounds has a hydrogen atom connected to the position: The other three compounds from Problem do not contain a hydrogen atom connected to the position and, therefore, cannot be prepared from the reaction between a hydride reducing agent (NaB 4 or LA) and a ketone or aldehyde C Mg C 3 C 3 C Mg C3 C3 C3 C 3 C 3 C 3 In this case, 3 + must be used as a proton source because water is not sufficiently acidic to protonate a phenolate ion (see Section 13.2, Acidity of Alcohols and Phenols) TMS, Et 3 N TMS 1) Mg TMS 2) 3) 2 TBAF
9 CAPTER TMS, Et 3 N TMS 1) Mg 2) Me (0.5 equivalents) 3) 2 TBAF TMS TMS ) Ts, py 2) Na P 3 1) Ts, py 2) Na S 2 py
10 288 CAPTER 13 d) 1) Ts, py 2) Na P 3 e) 1) Ts, py 2) Na S 2 py f) 1) Ts, py 2) Na P ) Ts, py 2) Na Na S 4 heat + major minor 1) Ts, py 2) NaEt
11 CAPTER PCC C 2 2 Na 2 Cr S 4, 2 xs Cr acetone PCC C 2 2 e) PCC C 2 2 f) Na 2 Cr S 4, ) Na 2) PCC, C 2 2 1) B 3 TF 2) 2 2, Na 3) PCC, C 2 2
12 290 CAPTER 13 1) dilute 2 S 4 2) Na 2 Cr 2 7, 2 S 4, 2 1) 2 2) xs NaN 2 3) 2 4) 2 S 4, 2, gs 4 d) 1) g(a 2, 2 2) NaB 4 3) Na 2 Cr 2 7, 2 S 4, 2 1) 2 2) xs NaN 2 3) 2 4) 2 S 4, 2, gs ) 2, Lindlar's Catalyst 2) B 3 TF 3) 2 2, Na 1) 9-BBN 2) 2 2, Na 3) LA 4) 2 2 S 4, heat 1) 2 1) Ts, py 2) t-buk 2) xs NaN 2 3) 2
13 CAPTER d) 1) B 3 TF 2) 2 2, Na 3) PCC, C 2 2 e) 1) 2 S 4, heat 2) 2, Pt 1) Ts, py 2) NaEt 3) 2, Pt f) 2 S 4, heat 1) LA 2) 2 1) Ts, py 2) t-buk g) 2 S 4, heat 1) LA 2) 2 1) Ts, py 2) NaEt S 4, heat 1) Ts, py 2) NaEt S 4, heat 1) Ts, py 1) B 3 TF 2) 2 2, Na 2) NaEt
14 292 CAPTER ) EtMg 2) 2 3) Na 2 Cr 2 7, 2 S 4, 2 1) MeMg 2) 2 3) Na 2 Cr 2 7, 2 S 4, ) 2 2) xs NaN 2 3) 2 1) 9-BBN 2) 2 2, Na 1) MeMg 1) B 3 TF 2) 2 2, Na PCC C 2 2 2) 2 3) Na 2 Cr 2 7, 2 S 4, 2 1) NaN 2 1) 9-BBN 2) 2) 2 2, Na 1) EtMg 2) 2 3) Na 2 Cr 2 7, 2 S 4, 2 1) EtMg 2) 2 3) Na 2 Cr 2 7, 2 S 4, 2
15 CAPTER d) 1) Ts, py 2) t-buk 1) B 3 TF 2) 2 2, Na PCC, C 2 2 1) MeMg 2) 2 3) Na 2 Cr 2 7, 2 S 4, 2 e) 1) 9-BBN 2) 2 2, Na 1) MeMg 2) 2 3) Na 2 Cr 2 7, 2 S 4, 2 f) 1) Na 2 Cr 2 7, 2 S 4, 2 2) MeMg 3) ) MeMg 2) 2 2 dilute 2 S 4 C C Na Lindlar's Catalyst 1) Mg 2) 3) 2 2 S 4, 2 gs 4 1) LA 2) 2
16 294 CAPTER 13 C C Na 2 Lindlar's Catalyst 1), RR 2) Na 1) 9-BBN 2) 2 2, Na 1) LA 2) 2 d) C C Na 1) 9-BBN 2) 2 2, Na 1) EtMg 2) 2 1) NaN 2 2) Et 2 S 4, 2 1) LA gs 4 2) propyl-1-pentanol (R)-4-methyl-2-pentanol 2-bromo-4-methylphenol d) (1R,2R)-2-methylcyclohexanol N N 2 N 2
17 CAPTER d) e) f) butanol 2-butanol 2-methyl-2-propanol 2-methyl-1-propanol Increasing acidity Increasing acidity Increasing acidity N 2
18 296 CAPTER bromobutane 1-chlorobutane 1-chlorobutane d) trans-2-butene e) f) Li g) h) Na i) TMS j) Ts k) Na l) K PCC C 2 2
19 CAPTER Na 2 Cr S 4, 2 1) PCC, C2 2 2) EtMg 3) 2 d) 1) PCC, C 2 2 2) EtMg 3) 2 4) Na 2 Cr 2 7, 2 S 4, 2 5) MeMg 6) 2 e) 1) PCC, C 2 2 2) PrMg 3) 2 4) Na 2 Cr 2 7, 2 S 4, ) 2) 2 Mg 1) MeMg 2) 2 1) PrMg 2) 2 1) Mg 2) 2
20 298 CAPTER 13 1) EtMg 2) 2 1) PrMg 2) 2 d) 1) MeMg 2) 2 1) EtMg 2) 2 1) PrMg 2) d) ) EtMg 2) 2 3) Na 2 Cr 2 7, 2 S 4, 2
21 CAPTER ) LA 2) 2 NaB 4 Me The major product is 1-methylcyclohexanol (resulting from Markvonikov addition), which is a tertiary alcohol. Tertiary alcohols do not generally undergo oxidation. The minor product (2-methylcyclohexanol) is a secondary alcohol and can undergo oxidation to yield a ketone Mg Mg 1) 2 S 4 2) 2 heat Compound A Compound B Compound C
22 300 CAPTER ) MeMg 2) 2 1) Ts, py 2) t-buk 1) PhMg 2) 2 Na 2 Cr S 4, 2 1) B 3 TF 2) 2 2, Na P 3 1) Mg PCC C 2 2 2) 3) ) Ts 1), RR 2) NaEt 2) Mg Na 2 Cr 2 7 1) PrMg 2 S 4, 2 2) 2
23 CAPTER Al Al Me B S S 2 py + S 2 + S S N S
24 302 CAPTER 13 P P S N P 2 Al Al Na 2 Cr S 4, 2 PCC C 2 2 PCC C 2 2 d) Na 2 Cr S 4, 2 e) 1) LA 2) 2 f) 1) LA 2) ) 3 2) DMS 3) Excess LA 4) 2
25 CAPTER ) 3 2) DMS 3) Excess LA 4) 2 1) 3 2) DMS 3) Excess LA 4) 2 d) 1) EtMg 2) 2 3) Na 2 Cr 2 7, 2 S 4, 2 4) EtMg 5) 2 e) 1) LA 2) 2 3) Ts, pyridine Ts f) 1) 3 + 2) Na 2 Cr 2 7, 2 S 4, 2 3) PhMg 4) 2 Ph C Mg 3 C 3 C
26 304 CAPTER 13 C Mg C 3 C Mg C 3 C 3 C 3 C 3 C 3 C ) 9-BBN 2) 2 2, Na PCC C 2 2 1) LA 2) 2 1) Ts 2) NaEt 1) 2 2) xs NaN 2 3) 2 2, Lindlar's Catalyst Na P 3 1) B 3 TF 2) 2 2, Na, RR t-buk
27 CAPTER ) MeMg 2) 2 3) Na 2 Cr 2 7, 2 S 4, 2 1) LA 2) 2 3) Ts, py 4) NaEt 1) LA 2) 2 3) Ts, py 4) NaEt 5) 3 6) DMS d) 1) MeMg 2) 2 3) Ts, py 4) t-buk e) 1) Na 2) PCC, C 2 2 f) 1) Na 2) PCC, C 2 2 3) MeMg 4) 2 5) Na 2 Cr 2 7, 2 S 4, 2
28 306 CAPTER 13 g) 1) dilute 2 S 4 2) Na 2 Cr 2 7, 2 S 4, 2 h) 1) dilute 2 S 4 2) Na 2 Cr 2 7, 2 S 4, 2 3) MeMg 4) 2 i) 1) dilute 2 S 4 2) Na 2 Cr 2 7, 2 S 4, 2 3) MeMg 4) conc. 2 S 4, heat j) 1) gs 4, 2 S 4, 2 2) MeMg 3) 2 k) 1) dilute 2 S 4 2) Na 2 Cr 2 7, 2 S 4, 2 3) MeMg 4) 2 l) 1) EtMg 2) 2 m) 1) LA 2) conc. 2 S 4
29 CAPTER n) 1) LA 2) 2 3) Ts, Et 3 N 4) t-buk o) 1) LA 2) 2 3) Ts, Et 3 N 4) t-buk 5) B 3 TF 6) 2 2, Na p) 1) MeMg 2) 2 3) conc. 2 S 4, heat q) 1) EtMg 2) 2 r) 1) LA 2) 2 3) P 3 s) 1) B 3 TF 2) 2 2, Na 3) PCC, C 2 2 4) MeMg 5) 2
30 308 CAPTER Al Al Al 2 Al
31 CAPTER C Mg C 3 C 3 C Mg C 3 C 3 2 C 3 C 3 C Mg C 3 3 C C 3 C Mg 3 C C 3 C 3 C 3 C 3 C 3 C ) 2, hv 2) NaMe 1) B 3 TF 2) 2 2, Na 3) Na 2 Cr 2 7, 2 S 4, 2 1) MeMg 2) 2 2 Pt conc. 2 S 4 heat
32 310 CAPTER C 3 Al Al - C 3 Al S - 2 methyl shift ne carbon atom is oxidized from an oxidation state of +1 to an oxidation state of +2, while the other carbon atom is reduced from an oxidation state of +1 to an oxidation state of 0. verall, the starting material does not undergo a net change in oxidation state and is, therefore, neither reduced nor oxidized.
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