
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Question
- An ester W with a molecular formula of C6H12O2 is optically active. When W is undergone acidic hydrolysis, compound X, C2H4O2 and an alcohol Y are formed. Alcohol Y is optically active and gives a yellow precipitate with alkaline iodine. Oxidation of Y produces Z which is optically inactive
- Identify compounds W, X, Y and Z.
- Write balanced equations for the formation of alcohol Y.
- Other than using alkaline iodine, suggest how you would differentiate between X and Y.
- State how Z reacts (if any) with,
- Alkaline iodine
- 2,4-dinitrophenylhydrazine
- Tollen’s reagent
Expert Solution

This question has been solved!
Explore an expertly crafted, step-by-step solution for a thorough understanding of key concepts.
Step by stepSolved in 3 steps with 4 images

Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- A cyclic, non-aromatic compound containing an attached carboxyl group is named by naming the cyclic compound exclusive of the –COOH group and then adding the suffix - carboxylic acid. Draw the structure of cis-2-methylcyclopentanecarboxylic acid.arrow_forwardProvide the major organic products for the following reactions.arrow_forwardWhat is the structure of the alcohol produced when 3-methyl-1-pentene undergoes (a) acid catalyzed hydration (b) oxymercuration/demercuration (c) hydroboration/oxidationarrow_forward
- Draw the structures and provide the names of all the isomeric alcohols that have the molecular formula C4H10Oarrow_forwardIn an esterification reaction, a carboxylic acid reacts with an excess of alcohol in acidic conditions to form an ester. Draw the structure of the ester product in the reaction between pentanoic acid and 1‑propanol. pentanoic acid+ 1-propanol= ester+ H20 structure of ester product neededarrow_forward1. Write a reaction showing how the compound ethanoic propanoic anhydride is prepared. Draw and name all constituional isomers of a compound having the molecular formula C4H&O2. 2.arrow_forward
- Esterication is the reaction of a carboxylic acid (RCOOH) with an alcohol (R'OH) to form an ester (RCOOR') with loss of water. Equation [1] is an example of an intermolecular esterication reaction. Equation [2] is an example of an intramolecular esterication reaction; that is, the carboxylic acid and alcohol are contained in the same starting material, forming a cyclic ester as product. The equilibrium constants for both reactions are given. Explain why Keq is different for these two apparently similar reactions.arrow_forwardSalsalate, which is an ester formed by the reaction of two molecules of salicylic acid, is another salicylate used as an aspirin alternative for those who are hypersensitive to aspirin. Draw the structures of salicylic acid and salsalate.arrow_forwardAlkenes can be converted to alcohols by reaction with mercuric acetate to form a β-hydroxyalkylmercury(II) acetate compound, a reaction called oxymercuration. Subsequent reduction with NaBH4 reduces the C–Hg bond to a C–H bond, forming the alkyl alcohol, a reaction called demercuration. Draw the structures of the Hg-containing compound(s) and the final alcohol product(s) formed in the following reaction sequence, omitting byproducts. If applicable, draw hydrogen at a chirality center and indicate stereochemistry via wedge-and-dash bonds.arrow_forward
- Alkenes can be converted to alcohols by reaction with mercuric acetate to form a β-hydroxyalkylmercury(II) acetate compound, a reaction called oxymercuration. Subsequent reduction with NaBH4 reduces the C–Hg bond to a C–H bond, forming the alkyl alcohol, a reaction called demercuration. Draw the structures of the Hg-containing compound(s) and the final alcohol product(s) formed in the following reaction sequence, omitting byproducts. If applicable, draw hydrogen at a chirality center and indicate stereochemistry via wedge-and-dash bonds.arrow_forwardPrimary alcohols can react with certain alkenes to give ethers. If a primary alcohol reacts with dihydropyran in the presence of acid only Product A is formed. Why is A formed over B? And what is the product of the reaction if N-propyl alcohol is the alcohol? H+ + FOR H OR A + B OR Harrow_forwardCompounds X and Y have the formula C6H12. Both X and Y react with one molar equivalent of hydrogen in the presence of a palladium catalyst to form 2-methylpentane. The heat of hydrogenation of X is less than that of Y. X and Y react with HBr to form a mixture of the same bromoalkanes, and they both undergo hydroboration/oxidation to give a mixture of the same alcohols. What is the structure of Y? • In cases where there is more than one answer, just draw one. + ChemDoodlearrow_forward
arrow_back_ios
arrow_forward_ios
Recommended textbooks for you
- ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage LearningChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill EducationPrinciples of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
- Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill EducationChemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage LearningElementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY

Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning

Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education

Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning

Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education

Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning

Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY