Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Videos
Textbook Question
Chapter 14, Problem 14.43SP
Give the structures of the intermediates represented by letters in this synthesis.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Synthesis: Show how you would carry out the following synthesis. Include the reagents you would need for each step and the structure of the intermediate products formed in each step. You may use any inorganic reagents you need and organic reagents of four or fewer carbons.
Write a reaction equation sequence for the following synthetic conversion. Eachreaction step must be represented by a complete reaction equation in which substrate,reagents and products are shown. Mechanisms are not required.
Alcohols are acidic in nature. Therefore, a strong base can
abstract the acidic hydrogen atom of the alcohol in a process
known as deprotonation. The alcohol forms an alkoxide ion by
losing the proton attached to the oxygen atom of the hydroxyl (
-OH) group. The alkoxide formed can act as a base or a
nucleophile depending on the substrate and reaction conditions.
However, not all bases can abstract the acidic proton of alcohols
and not all alcohols easily lose the proton. Deprotonation
depends on the strength of the base and the acidity of the
alcohol. Strong bases, such as NaNH2, can easily abstract a
proton from almost all alcohols. Likewise, more acidic alcohols
lose a proton more easily.
Determine which of the following reactions would undergo deprotonation based on the strength of the base and the acidity of the alcohol.
Check all that apply.
► View Available Hint(s)
CH3CH,OH + NH3 →CH,CH,O-NH
CH3
CH3
H3C-C-H+NH3 → H3 C-C-H
OH
O-NH
CH3CH2OH + NaNH, → CH3CH,O-Na* + NH3
CHC12
Cl₂…
Chapter 14 Solutions
Organic Chemistry (9th Edition)
Ch. 14.2C - Rank the given solvents in decreasing order of...Ch. 14.2D - Prob. 14.2PCh. 14.2D - In the presence of 18-crown-6, potassium...Ch. 14.3B - Give a common name (when possible) and a...Ch. 14.3C - Prob. 14.5PCh. 14.3C - Name the following heterocyclic ethers.Ch. 14.4 - Propose a fragmentation to account for each...Ch. 14.5 - Prob. 14.8PCh. 14.5 - Prob. 14.9PCh. 14.6 - Prob. 14.10P
Ch. 14.7 - Explain why bimolecular condensation is a poor...Ch. 14.7 - Prob. 14.12PCh. 14.7 - Prob. 14.13PCh. 14.8 - Prob. 14.14PCh. 14.8 - Prob. 14.15PCh. 14.8 - Prob. 14.16PCh. 14.10A - Prob. 14.17PCh. 14.10A - Prob. 14.18PCh. 14.10B - Prob. 14.19PCh. 14.11B - Show how you would accomplish the following...Ch. 14.11B - Prob. 14.21PCh. 14.12 - Prob. 14.22PCh. 14.12 - Prob. 14.23PCh. 14.12 - Prob. 14.24PCh. 14.13 - Prob. 14.25PCh. 14.13 - Prob. 14.26PCh. 14.14 - Prob. 14.27PCh. 14.15 - Give the expected products of the following...Ch. 14 - Write structural formulas for the following...Ch. 14 - Give common names for the following compounds. a....Ch. 14 - Give IUPAC names for the following compounds. a....Ch. 14 - Glycerol (propane-1,2,3-triol) is a viscous syrup...Ch. 14 - Prob. 14.33SPCh. 14 - Show how you would make the following ethers,...Ch. 14 - (A true story.) An inexperienced graduate student...Ch. 14 - Prob. 14.36SPCh. 14 - a. Show how you would synthesize the pure (R)...Ch. 14 - a. Predict the values of m/z and the structures of...Ch. 14 - The following reaction resembles the...Ch. 14 - Prob. 14.40SPCh. 14 - Prob. 14.41SPCh. 14 - Prob. 14.42SPCh. 14 - Give the structures of the intermediates...Ch. 14 - Prob. 14.44SPCh. 14 - Show how you would synthesize the following ethers...Ch. 14 - Prob. 14.46SPCh. 14 - Prob. 14.47SPCh. 14 - Prob. 14.48SPCh. 14 - An acid-catalyzed reaction was carried out using...Ch. 14 - Propylene oxide is a chiral molecule. Hydrolysis...Ch. 14 - Prob. 14.51SPCh. 14 - Prob. 14.52SPCh. 14 - Prob. 14.53SPCh. 14 - Prob. 14.54SPCh. 14 - In 2012, a group led by Professor Masayuki Satake...
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
- single reaction sequence: a certain ketone undergoes alkylation to give new ketone, when reacted with a base and then an alkylating agent, 1-bromopropane. What is the structure of the final ketone product?arrow_forwardHow many elimination products will be formed in the following reaction?arrow_forwardThree of these reactions proceed using the same intermediate. Draw the structure of that intermediate.arrow_forward
- A problem often encountered in the oxidation of primary alcohols to acids is that esters are sometimes produced as by-products. For example, oxidation of ethanol yields acetic acid and ethyl acetate: Propose a mechanism to account for the formation of ethyl acetate. Take into account the reversible reaction between aldehydes and alcohols:arrow_forwardWhich of the reaction conditions could afford the following transformation?arrow_forwardShow how to control the stereochemistry and regiochemistry (orientation) of additions to alkenes to obtain the products we want.arrow_forward
- When trans-2-chloro-1-cyclohexanol is treated with a base, cyclohexene oxide is the product. However, when cis-2-chloro-1-cyclohexanol is treated with a base, the product is cyclohexanone. Write the mechanism for each of the two reactions.arrow_forwardAcetal formation must be catalyzed by an acid. Explain why it cannot be catalyzed by CH3O-.arrow_forwardWrite the structure(s) for the aldehyde(s) and/or ketone(s) that undergo an aldol addition reaction to form the product shown here. OH 2 Harrow_forward
- A synthetic organic molecule, G, which contains both aldehyde and ether functional groups, is subjected to a series of reactions in a multi-step synthesis pathway. In the first step, G undergoes a Wittig reaction, leading to the formation of an alkene, H. Subsequently, H is treated with an ozone (O3) reagent followed by a reducing agent in an ozonolysis reaction, resulting in the formation of two different products, I and J. Considering the functional groups present in G and the nature of the reactions involved, what are the most probable structures or functional groups present in products I and J? A. I contains a carboxylic acid group, and J contains an aldehyde group. B. I contains a ketone group, and J contains an alcohol group. C. I and J both contain aldehyde groups. D. I contains an ester group, and J contains a ketone group. Don't use chat gpt.arrow_forwardThe reaction is a nucleophilic substitution, A is OH- and B is an alkyl bromide. Give the reaction mechanism and explain your reasoning.arrow_forwardThe following reaction involves two sequential Heck reactions. Draw structural formu- las for each organopalladium intermediate formed in the sequence and show how the final product is formed. Note from the molecular formula given under each structural formula that this conversion corresponds to a loss of H and I from the starting material. Acetonitrile, CH,CN, is the solvent. 1% mol Pd(OAc), 4% mol Ph,P CH,CN C4H171 C4H16arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
EBK A SMALL SCALE APPROACH TO ORGANIC LChemistryISBN:9781305446021Author:LampmanPublisher:CENGAGE LEARNING - CONSIGNMENT
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
EBK A SMALL SCALE APPROACH TO ORGANIC L
Chemistry
ISBN:9781305446021
Author:Lampman
Publisher:CENGAGE LEARNING - CONSIGNMENT
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Seven Name Reactions in One - Palladium Catalysed Reaction (047 - 053); Author: Rasayan Academy - Jagriti Sharma;https://www.youtube.com/watch?v=5HEKTpDFkqI;License: Standard YouTube License, CC-BY