Chemistry: The Science in Context (Fourth Edition)
Chemistry: The Science in Context (Fourth Edition)
4th Edition
ISBN: 9780393124187
Author: Thomas R. Gilbert, Rein V. Kirss, Natalie Foster, Geoffrey Davies
Publisher: W. W. Norton & Company
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Chapter 13, Problem 13.142AP

(a)

Interpretation Introduction

To determine: The structures of the acid and alcohol formed by the metabolism of Tamiflu.

Interpretation: The structure of Tamiflu is given. The structures of the products formed by the metabolism of Tamiflu in the liver are to be drawn.

Concept introduction: The hydrolysis of an ester is the reaction in which a water molecule breaks the ester bond and adds a proton to the carboxylate group of one species and the hydroxide group to the alkyl group of the other species.

(b)

Interpretation Introduction

To determine: The functional group other that acidic group and chiral center in the structure of the active form of Tamiflu drug.

Interpretation: The functional group other that acidic group and chiral center in the structure of the active form of Tamiflu drug are to be identified.

Concept introduction: Functional group is a group of atoms responsible for the reactivity of the compound. Chiral center in a compound is the carbon that is attached to four different groups in a compound.

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3. SYNTHESIS. Propose a sequence of synthetic steps (FGI) that convert the starting material (SM) into the Target molecule. For each FGI in your proposed synthesis, specify the reagents / conditions, and draw the product(s) of that FGI. DO NOT INCLUDE the FGI mxn in the answer you submit. If an FGI requires two reagent sets, specify the order in which the reagent sets are added, e.g., i) Hg(OAc)2 / H₂O; ii) NaBH4/MeOH. Indicate the stereochemistry (if any) of the products of each FGI. FGI 1. Me Starting Material Source of all carbons in the Target molecule (can use multiple copies) Me Me Target molecule + enantiomer
curved arrows are used to illustate the flow of electrons. Using the provided starting and product structures, draw the curved electron-pushing arrows for the following reaction mechanism steps

Chapter 13 Solutions

Chemistry: The Science in Context (Fourth Edition)

Ch. 13.7 - Prob. 11PECh. 13.8 - Prob. 12PECh. 13.8 - Prob. 13PECh. 13 - Prob. 13.1VPCh. 13 - Prob. 13.2VPCh. 13 - Prob. 13.3VPCh. 13 - Prob. 13.4VPCh. 13 - Prob. 13.5VPCh. 13 - Prob. 13.6VPCh. 13 - Prob. 13.7VPCh. 13 - Prob. 13.8VPCh. 13 - Prob. 13.9VPCh. 13 - Prob. 13.10VPCh. 13 - Prob. 13.11VPCh. 13 - Prob. 13.12VPCh. 13 - Prob. 13.13VPCh. 13 - Prob. 13.14VPCh. 13 - Prob. 13.15VPCh. 13 - Prob. 13.16VPCh. 13 - Prob. 13.17QPCh. 13 - Prob. 13.18QPCh. 13 - Prob. 13.19QPCh. 13 - Prob. 13.20QPCh. 13 - Prob. 13.21QPCh. 13 - Prob. 13.22QPCh. 13 - Prob. 13.23QPCh. 13 - Prob. 13.24QPCh. 13 - Prob. 13.25QPCh. 13 - Prob. 13.26QPCh. 13 - Prob. 13.27QPCh. 13 - Prob. 13.28QPCh. 13 - Prob. 13.29QPCh. 13 - Prob. 13.30QPCh. 13 - Prob. 13.31QPCh. 13 - Prob. 13.32QPCh. 13 - Prob. 13.33QPCh. 13 - Prob. 13.34QPCh. 13 - Prob. 13.35QPCh. 13 - Prob. 13.36QPCh. 13 - Prob. 13.37QPCh. 13 - Prob. 13.38QPCh. 13 - Prob. 13.39QPCh. 13 - Prob. 13.40QPCh. 13 - Prob. 13.41QPCh. 13 - Prob. 13.42QPCh. 13 - Prob. 13.43QPCh. 13 - Prob. 13.44QPCh. 13 - Prob. 13.45QPCh. 13 - Prob. 13.46QPCh. 13 - Prob. 13.47QPCh. 13 - Prob. 13.48QPCh. 13 - Prob. 13.49QPCh. 13 - Prob. 13.50QPCh. 13 - Prob. 13.51QPCh. 13 - Prob. 13.52QPCh. 13 - Prob. 13.53QPCh. 13 - Prob. 13.54QPCh. 13 - Prob. 13.55QPCh. 13 - Prob. 13.56QPCh. 13 - Prob. 13.57QPCh. 13 - Prob. 13.58QPCh. 13 - Prob. 13.59QPCh. 13 - Prob. 13.60QPCh. 13 - Prob. 13.61QPCh. 13 - Prob. 13.62QPCh. 13 - Prob. 13.63QPCh. 13 - Prob. 13.64QPCh. 13 - Prob. 13.65QPCh. 13 - Prob. 13.66QPCh. 13 - Prob. 13.67QPCh. 13 - Prob. 13.68QPCh. 13 - Prob. 13.69QPCh. 13 - Prob. 13.70QPCh. 13 - Prob. 13.71QPCh. 13 - Prob. 13.72QPCh. 13 - Prob. 13.73QPCh. 13 - Prob. 13.74QPCh. 13 - Prob. 13.75QPCh. 13 - Prob. 13.76QPCh. 13 - Prob. 13.77QPCh. 13 - Prob. 13.78QPCh. 13 - Prob. 13.79QPCh. 13 - Prob. 13.80QPCh. 13 - Prob. 13.81QPCh. 13 - Prob. 13.82QPCh. 13 - Prob. 13.83QPCh. 13 - Prob. 13.84QPCh. 13 - Prob. 13.85QPCh. 13 - Prob. 13.86QPCh. 13 - Prob. 13.87QPCh. 13 - Prob. 13.88QPCh. 13 - Prob. 13.89QPCh. 13 - Prob. 13.90QPCh. 13 - Prob. 13.91QPCh. 13 - Prob. 13.92QPCh. 13 - Prob. 13.93QPCh. 13 - Prob. 13.94QPCh. 13 - Prob. 13.95QPCh. 13 - Prob. 13.96QPCh. 13 - Prob. 13.97QPCh. 13 - Prob. 13.98QPCh. 13 - Prob. 13.99QPCh. 13 - Prob. 13.100QPCh. 13 - Prob. 13.101QPCh. 13 - Prob. 13.102QPCh. 13 - Prob. 13.103QPCh. 13 - Prob. 13.104QPCh. 13 - Prob. 13.105QPCh. 13 - Prob. 13.106QPCh. 13 - Prob. 13.107QPCh. 13 - Prob. 13.108QPCh. 13 - Prob. 13.109QPCh. 13 - Prob. 13.110QPCh. 13 - Prob. 13.111QPCh. 13 - Prob. 13.112QPCh. 13 - Prob. 13.113QPCh. 13 - Prob. 13.114QPCh. 13 - Prob. 13.115QPCh. 13 - Prob. 13.116QPCh. 13 - Prob. 13.117QPCh. 13 - Prob. 13.118QPCh. 13 - Prob. 13.119QPCh. 13 - Prob. 13.120QPCh. 13 - Prob. 13.121QPCh. 13 - Prob. 13.122QPCh. 13 - Prob. 13.123QPCh. 13 - Prob. 13.124QPCh. 13 - Prob. 13.125QPCh. 13 - Prob. 13.126QPCh. 13 - Prob. 13.127QPCh. 13 - Prob. 13.128QPCh. 13 - Prob. 13.129QPCh. 13 - Prob. 13.130QPCh. 13 - Prob. 13.131QPCh. 13 - Prob. 13.132QPCh. 13 - Prob. 13.133QPCh. 13 - Prob. 13.134QPCh. 13 - Prob. 13.135APCh. 13 - Prob. 13.136APCh. 13 - Prob. 13.137APCh. 13 - Prob. 13.138APCh. 13 - Prob. 13.139APCh. 13 - Prob. 13.140APCh. 13 - Prob. 13.141APCh. 13 - Prob. 13.142APCh. 13 - Prob. 13.143APCh. 13 - Prob. 13.144APCh. 13 - Prob. 13.145APCh. 13 - Prob. 13.146APCh. 13 - Prob. 13.147APCh. 13 - Prob. 13.148APCh. 13 - Prob. 13.149APCh. 13 - Prob. 13.150APCh. 13 - Prob. 13.151AP
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