Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Chapter 17.9, Problem 11P
Interpretation Introduction
Interpretation:
The absolute configuration of the
Concept Introduction:
>Sharpless epoxidation involves the oxidation of double bond between carbon atoms to form an
This oxidation occurs only in allylic alcohol. This is an enantioselective oxidation, which means predominantly one enantiomer is formed.
>Sharpless reagents are tert-butyl hydroperoxide,
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Chapter 17 Solutions
Organic Chemistry - Standalone book
Ch. 17.1 - Prob. 1PCh. 17.2 - The heats of combustion of 1, 2-epoxybutane...Ch. 17.3 - Prob. 3PCh. 17.4 - Prob. 4PCh. 17.5 - Prob. 5PCh. 17.6 - Problem 17.6 (a) Write equations describing two...Ch. 17.6 - Problem 17.7 Only one combination of alkyl halide...Ch. 17.6 - Prob. 8PCh. 17.8 - Prob. 9PCh. 17.8 - Prob. 10P
Ch. 17.9 - Prob. 11PCh. 17.10 - Problem 17.12 Classify the bromohydrins formed...Ch. 17.11 - Prob. 13PCh. 17.11 - Prob. 14PCh. 17.12 - Prob. 15PCh. 17.12 - Prob. 16PCh. 17.14 - Prob. 17PCh. 17.15 - Prob. 18PCh. 17.16 - Prob. 19PCh. 17.17 - Problem 17.20 There is another oxygen-stabilized...Ch. 17 - Prob. 21PCh. 17 - Many ethers, including diethyl ether, are...Ch. 17 - Although epoxides are always considered to have...Ch. 17 - The name of the parent six-membered...Ch. 17 - Prob. 25PCh. 17 - Prob. 26PCh. 17 - Prob. 27PCh. 17 - Prob. 28PCh. 17 - Prob. 29PCh. 17 - Given that: does the product of the analogous...Ch. 17 - Prob. 31PCh. 17 - Prob. 32PCh. 17 - Prob. 33PCh. 17 - Prob. 34PCh. 17 - Prob. 35PCh. 17 - Prob. 36PCh. 17 - When (R)-(+)-2-phenyl-2-butanol is allowed to...Ch. 17 - Prob. 38PCh. 17 - Prob. 39PCh. 17 - Write a mechanism for the following reaction.Ch. 17 - Prob. 41PCh. 17 - Prob. 42PCh. 17 - Prob. 43PCh. 17 - Prob. 44PCh. 17 - Prob. 45PCh. 17 - Prob. 46DSPCh. 17 - Prob. 47DSPCh. 17 - Prob. 48DSPCh. 17 - Prob. 49DSPCh. 17 - Epoxide Rearrangements and the NIH Shift This...Ch. 17 - Epoxide Rearrangements and the NIH Shift This...
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- Problem 11 of 32 Draw the product of the substitution reaction shown below. Ignore the inorganic byproducts. CH3CH₂I DMSO OO (+) Submit Naarrow_forward9) Which of the following pairs will form only one product of aldol addition, if the second component will be slowly added to the reaction mixture? Answer A) which CH3 H3C H3C. H3C B) H3C. H3C CH3 H H3C. D) H3C. CH3 H3C H CH3 + H3C CH3 thaich CH3 H3C CH3 l H CH3 Harrow_forwardPROBLEM 14.62 Even though naphthalene and anthra- cene are polynuclear aromatic compounds, they undergo the Diels-Alder reaction. For example, anthracene readily reacts with maleic anhydride. However, the reaction of naphthalene with maleic anhydride proceeds efficiently only under high pressure. + + O xylene 140 °C, 10 min 100 °C 9.6 kbar, 17 h ?arrow_forward
- Problem 8.1 a) Choose the most atom economical protecting group (PG) for the alcohol that would be stable to the strong basic Horner-Emmons reagent in the reaction with the aldehyde to make the alkene given below (picture attached). b) What is the approximate pKa of a primary alcohol? Estimate the pKa of the Horner-Emmons conjugate acid (H instead of Li) based on the pKa of a simple beta -diester. c) Draw an acid-base reaction between an alcohol and a beta diester base. Which side would the equilibrium be skewed towards? By how many orders of magnitude? d) How could you avoid the need for a protecting group in this reaction?arrow_forwardProblem 8.1 a) Choose the most atom economical protecting group (PG) for the alcohol that would be stable to the strong basic Horner - Emmons reagent in the reaction with the aldehyde to make the alkene given below (picture attached). b) What is the approximate pKa of a primary alcohol? Estimate the pKa of the Horner - Emmons conjugate acid (H instead of Li) based on the pKa of a simple beta - diester. c) Draw an acid-base reaction between an alcohol and a beta diester base. Which side would the equilibrium be skewed towards? By how many orders of magnitude? d) How could you avoid the need for a protecting group in this reaction? PG.O ནཱནཱགཱ, PG. EtO-P Eto OEt H OEt + O=P EtO-P Eto +7-0arrow_forwardProblem 25 of 38 Draw the two products of the reaction shown below. Assume only 1 equivalent of HBr is consumed in this reaction. Ignore any inorganic byproducts. HBr Submit Qarrow_forward
- Problem 17.7 Give the structures of the starting materials that would be required to synthesize the following compounds. O CH, C-CH, (d) (c) CH3arrow_forwardQuestion 15 What synthetic goal is achieved by subjecting an alkene to a hydroboration-oxidation sequence? O syn-dihydroxylation anti-Markovnikov addition of H2O with anti stereochemistry O Markovnikov addition of H2O wherein skeletal rearrangement is promoted O Markovnikov addition of H2O wherein skeletal rearrangement is prevented anti-Markovnikov addition of H2O with syn stereochemistryarrow_forwardIn the hydration of 1-methyl-1-vinylcyclopentane, the major product is shown: H20 HO. H,SO4 a) Draw the complete mechanism for this transformation, using good curved arrow notation. Identify the HOMO and LUMO in the first step.arrow_forward
- e skill 17.18 Propose an efficient synthesis for each of the following transformations: (a) (c) (e) N= O OH (b) of (d) OH HD (f)arrow_forwardA re the following reactions regioselective? 1) (3R)-3-bromo-3,4-d'methy Ihexane is refluxed with KOH 2) (28)-2-iodo-3,4 dimethylheptane is refluxed with KOCCCHa)s 3) (R)-3- iodohexane is refluxed with HzO 4) (22)2-bromo-3,4-dimethyIhexane is refluxed with H20arrow_forwardProblem 18 of 50 Submit Curved arrows are used to illustrate the flow of electrons. Follow the arrows and draw the product formed in this reaction. Include all lone-pairs. Ignore any inorganic byproducts. HNO3 H2SO4 مل علم Нarrow_forward
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