Concept explainers
(a)
Interpretation: A stepwise mechanism for the formation of MOM ether from cyclohexanol is to be stated.
Concept introduction: An alkoxide salt is required to prepare ether. The alkoxide salts are prepared from alcohols through the Bronsted-Lowry acid-base reaction. In this reaction,
(b)
Interpretation: The
Concept introduction: Acetals are the groups in which carbon atom is bonded with two
(c)
Interpretation: The other products that are formed besides cyclohexanol from the aqueous hydrolysis of the MOM ether are to be predicted, and a stepwise mechanism for the formation of each product is to be drawn.
Concept introduction: Acetals are the groups in which carbon atom is bonded with two
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Organic Chemistry
- H3C. 00 H3C. CH3 XII HO: OCH3 Aldehydes and ketones react reversibly with two equivalents of alcohol in the presence of an acid catalyst to give acetals. Alcohols are poor nucleophiles, and so protonation of the carbonyl oxygen is used to make the carbonyl carbon a stronger electrophile. Addition of the first equivalent of alcohol gives a hemiacetal, a hydroxyether. Addition of the second equivalent of alcohol is accompanied by loss of water to yield the product acetal. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions 2 CH₂OH HCI catalyst CH3 H3C H-OH₂ H3CO OCH3 CH3 H3C. H₂O: OCH3 CH3 H₂O Чаarrow_forwardDraw the organic product(s) formed when CH3CH₂CH₂OH is treated with each reagent. a. H₂SO4 d. HBr g. TsCl, pyridine b. NaH h. [1] NaH; [2] CH₂CH₂Br e. SOCI₂, pyridine f. PBr3 c. HCI + ZnCl₂ Hint: NaH deprotonates the alcohol forming an alkoxidearrow_forward4. Which of the following reactions can be used to prepare 11-diphenyl-1-propanol? OH I. II. III. CH₂CH₂C снене-ось CH₂CH₂C -OCH3 PO 1. 2. H₂00 1. ? 2. H30Ⓡ MgBr MgBr 1. CH3CH₂ MgBr 2. H30arrow_forward
- 10. Write chemical equations for the reaction of ethyl propanoate with each reagent below. a) LIAIH4/ H3O* b) NH3 d) NaOH c) C2H5NH2arrow_forwardWhat are the chemical reactions for the alcohol? Choices Oxidation of primary alcoholOxidation of secondary alcoholOxidation of tertiary alcoholHydration of alkeneIntramolecular dehydrationIntermolecular dehydrationCombustionHalogenation with hydrogen halidesHalogenation with phosphorus trihalidesarrow_forward5. Describe an efficient synthesis of 1-methyl-1-cyclohexanol from cyclohexanol. Show the structure of the reagents, reactants and products from each step. Cyclohexanol -------> -----> 1-methyl-1-cyclohexanolarrow_forward
- Besides the tert-butyldimethylsilyl ethers, there are many other widely used alcohol protecting groups. For example, an alcohol such as cyclohexanol can be converted to a methoxy methyl ether (a MOM protecting group) by treatment with base and chloromethyl methyl ether, ClCH2OCH3. The protecting group can be removed by treatment with aqueous acid.a. Write a stepwise mechanism for the formation of a MOM ether from cyclohexanol.b. What functional group comprises a MOM ether?c. Besides cyclohexanol, what other products are formed by aqueous hydrolysis of the MOM ether? Draw a stepwise mechanism that accounts for formation of each product.arrow_forwardIn an alkoxymercuration-demercuration reaction, an alcohol adds to an alkene double bond. We already have the alkene starting material, so we must prepare the alcohol starting material. Draw the product of the following acid-catalyzed hydration reaction. 1) BH, THF 2) H,O2, NaOH II N. Close NV OH H,C CI Br P. 1.arrow_forward21. Provide the reagents necessary to carry out the following reaction. following conversion. CN 22. Provide the reactant for the NH₂ Ph3P=CHCH3 A. B. ܘܘܣ C. D. cyclohexanone cyclohexanecarbaldehyde cyclohexylpropanone 3-cyclohexylpropanalarrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning