Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Chapter 11, Problem 55P
Reaction of an alcohol with thionyl chloride in the presence of a tertiary
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a) Give the mechanistic symbols (SN1, SN2, E1, E2) that are most consistent with each of the following statements:
we know that ethers, such as diethyl ether and tetrahydrofuran, are quite resistant to the action of dilute acids and require hot concentrated HI or HBr for cleavage. However, acetals in which two ether groups are linked to the same carbon undergo hydrolysis readily, even in dilute aqueous acid. How do you account for this marked difference in chemical reactivity toward dilute aqueous acid between ethers and acetals?
Show how the following ethers might be synthesized using (1) alkoxymercuration–demercuration and (2) the Williamson synthesis. (When one of these methods cannot beused for the given ether, point out why it will not work.) thyl cyclohexyl ether
Chapter 11 Solutions
Organic Chemistry
Ch. 11 - Prob. 1PPCh. 11 - Practice Problem 11.2 Give bond-line formulas and...Ch. 11 - Prob. 3PPCh. 11 - Prob. 4PPCh. 11 - Prob. 5PPCh. 11 - Prob. 6PPCh. 11 - Prob. 7PPCh. 11 - PRACTICE PROBLEM
11.8 Show how you would prepare...Ch. 11 - PRACTICE PROBLEM
11.9 Write structures for...Ch. 11 - Prob. 10PP
Ch. 11 - Practice Problem 11.11
An exception to what is...Ch. 11 - Prob. 12PPCh. 11 - Prob. 13PPCh. 11 - Prob. 14PPCh. 11 - Prob. 15PPCh. 11 - Prob. 16PPCh. 11 - Prob. 17PPCh. 11 - Prob. 18PPCh. 11 - Practice Problem 11.19
Propose structures for each...Ch. 11 - Prob. 20PPCh. 11 - Prob. 21PPCh. 11 - Prob. 22PPCh. 11 - Prob. 23PPCh. 11 - Prob. 24PPCh. 11 - Give an IUPAC substitutive name for each of the...Ch. 11 - Prob. 26PCh. 11 - Prob. 27PCh. 11 - Prob. 28PCh. 11 - Prob. 29PCh. 11 - 11.30. Show how you might prepare 2-bromobutane...Ch. 11 - Prob. 31PCh. 11 - Prob. 32PCh. 11 - 11.33 What compounds would you expect to be formed...Ch. 11 - Considering A-L to represent the major products...Ch. 11 - Write structures for the products that would be...Ch. 11 - Prob. 36PCh. 11 - 11.37 Outlined below is a synthesis of the gypsy...Ch. 11 - Provide the reagents necessary for the following...Ch. 11 - 11.38. Predict the major product from each of the...Ch. 11 - Prob. 40PCh. 11 - Provide the reagents necessary to accomplish the...Ch. 11 - 11.41. Provide reagents that would accomplish the...Ch. 11 - Prob. 43PCh. 11 - 11.44 Write a mechanism that accounts for the...Ch. 11 - Prob. 45PCh. 11 - Prob. 46PCh. 11 - Prob. 47PCh. 11 - 11.47. Vicinal halo alcohols (halohydrins) can be...Ch. 11 - Prob. 49PCh. 11 - Prob. 50PCh. 11 - Prob. 51PCh. 11 - Prob. 52PCh. 11 - Prob. 53PCh. 11 - 11.57. When the 3-bromo-2-butanol with the...Ch. 11 - 11.58. Reaction of an alcohol with thionyl...Ch. 11 - Prob. 56PCh. 11 - Prob. 57PCh. 11 - Prob. 1LGPCh. 11 - Prob. 2LGPCh. 11 - Synthesize the compound shown below from...Ch. 11 - 11.1 Which set of reagents would effect the...Ch. 11 - Prob. 2QCh. 11 - 11.3 The following compounds have identical...Ch. 11 - Complete the following synthesis:Ch. 11 - Two configurations can actually be envisioned for...
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- The base-promoted rearrangement of an -haloketone to a carboxylic acid, known as the Favorskii rearrangement, is illustrated by the conversion of 2-chlorocyclohexanone to cyclopentanecarboxylic acid. It is proposed that NaOH first converts the a-haloketone to the substituted cyclopropanone shown in brackets and then to the sodium salt of cyclopentanecarboxylic acid. (a) Propose a mechanism for base-promoted conversion of 2-chlorocyclohexanone to the proposed intermediate. (b) Propose a mechanism for base-promoted conversion of the proposed intermediate to sodium cyclopentanecarboxylate.arrow_forwardWittig reactions with the following -chloroethers can be used for the synthesis of aldehydes and ketones. (a) Draw the structure of the triphenylphosphonium salt and Wittig reagent formed from each chloroether. (b) Draw the structural formula of the product formed by treating each Wittig reagent with cyclopentanone. Note that the functional group is an enol ether or, alternatively, a vinyl ether. (c) Draw the structural formula of the product formed on acid-catalyzed hydrolysis of each enol ether from part (b).arrow_forwardDraw a structural formula for the major organic product of each reaction and specify the most likely mechanism by which each is formed. (g) CH3CH2ONa++CH2=CHCH2Clethanolarrow_forward
- Write a mechanism that accounts for the formation of ethyl isopropyl ether as one of the products in the following reaction. CI OEt HCI EtOHarrow_forward5. Optically pure 2-octyl sulfonate was treated with varying mixtures of water and dioxane, and the optical purity of the resulting product (2-octanol) was found to vary with the ratio of water to dioxane, as shown in the following table (J. Am. Chem. Soc. 1965, 87, 287-291). Given that dioxane possesses fairly nucleophilic oxygen atoms, provide a complete mechanism that explains the variation in in the product's optical purity due to changes in solvent composition. Hint, the solvent is doing more here than just dissolving.. it is partaking in the reaction. Solvent Ratio (water : dioxane) 25:75 50: 50 75: 25 100 :0 Optical purity of (S)-2-octanol 77% 88% 95% 100% H20 он (R)-2-Octyl sulfonate (optically pure) (S)-2-Octanol (dioxane)arrow_forwardThe following substances can be prepared by a nucleophilic addition reaction between an aldehyde or ketoneand a nucleophile. Identify the reactants from which they were prepared. If the substance is an acetal, identifythe carbonyl compound and the alcohol; if it is an imine or enamine, identify the carbonyl compound and theamine. You do not have to consider stereochemistry. In cases where there is more than one answer, just giveone. Use Grignard reagents when an organometallic reagent is required. Draw the Grignard reagent as acovalent magnesium bromide.arrow_forward
- Show how you would synthesize the following compounds, starting with benzene or toluene and any necessary reagents. Assume para is the major product (and separable from ortho) in ortho, para mixtures.arrow_forwarda) Cycohexanone reacts with 1,3-propanediol under acid catalysis to form the cyclic acetal. Write down the reaction mechanism and explain why the use of cyclic acetals as protecting groups is preferred over open- chain acetals. b) Eugenol (see below) is made from cloves. Give the structural formulas of the products which are formed after reaction of eugenol with i) BH3, then H2O2 / NaOH or after reaction with ii) acetic anhydride. OH Eugenolarrow_forwardTreatment of a cyclic ketone with diazomethane is a method for accomplishing a ring-expansion reaction. The reaction involves the initial nucleophilic attack by diazomethane on the carbonyl carbon to form a tetrahedral intermediate. Collapse of this intermediate is accompanied by bond migration and loss of N,. For example, treatment of cyclohexanone with diazomethane yields cycloheptanone. CH2N2, ether + N2 Draw the structure of the organic product(s) of the ring expansion of this compound: • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • Do not include lone pairs in your answer. They will not be considered in the grading. • Draw one structure per sketcher Add additional ketchers usina the dron down menu in the bottom right co Previous Nextarrow_forward
- The Dess–Martin reaction reacts an alcohol with the Dess–Martin periodinane. The first step displaces one of the acetate groups on the periodinane with the alcohol. A base then deprotonates one of the alpha protons, forming a new carbonyl bond, iodinane and acetic acid. The oxidation stops at this stage to give the aldehyde. Both Swern and Dess–Martin conditions will also convert a secondary alcohol to a ketone. Now apply what has just been discussed. Draw the major organic product.arrow_forwardWith organolithium and organomagnesium compounds, approach to the carbonyl carbon from the less hindered direction is generally preferred. Assuming this is the case, predict the structure of the major product formed by reaction of methylmagnesium bromide with 4-tert-butylcyclohexanone.arrow_forwardWhen bromomethane undergoes solvolysis in a solvent mixture composed of 90% water/10% acetone, the reaction rate is faster than when the same compound is solvolyzed in 80% water/20% acetone. Explain.arrow_forward
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