Organic Chemistry (9th Edition)
Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
bartleby

Concept explainers

Question
Book Icon
Chapter 8, Problem 8.65SP

(a)

Interpretation Introduction

To determine: The conversion of fumaric acid to (±)tartaricacid.

Interpretation: The given question stated that two butenedioic acids are called fumaric acids (trans) and maleic acid (cis) and 2,3Dihydroxybutanedioicacid is called tartaric acid. The given conversion is to be predicted.

Concept introduction: Osmium tetroxide also called osmic acid reacts with alkenes to form cyclic osmate ester. Hydrogen peroxide is used as an oxidizing agent to hydrolyze the osmate ester. The attack of oxygen from osmic acid to the double bond of alkene is from the same side. Thus they have syn stereochemistry.

(b)

Interpretation Introduction

To determine: The conversion of fumaric acid to meso-tartaric acid.

Interpretation: The given question stated that two butenedioic acids are called fumaric acids (trans) and maleic acid (cis) and 2,3Dihydroxybutanedioicacid is called tartaric acid. The given conversion is to be predicted.

Concept introduction: Epoxidation of alkene is an oxidation process. Epoxides are also called an oxirane and they are intermediates that are used to convert alkenes into other functional group. Peroxyacid is used to convert alkene into an epoxide.

The steps followed by the given reaction are stated as:

  • First step is the formation of epoxide.
  • Second step is the attack of water to opens the ring.
  • The third step is deprotonation that gives diol product.

(c)

Interpretation Introduction

To determine: The conversion of maleic acid to (±)tartaricacid.

Interpretation: The given question stated that two butenedioic acids are called fumaric acids (trans) and maleic acid (cis) and 2,3Dihydroxybutanedioicacid is called tartaric acid. The given conversion is to be predicted.

Concept introduction: Epoxidation of alkene is an oxidation process. Epoxides are also called an oxirane and they are intermediates that are used to convert alkenes into other functional group. Peroxyacid is used to convert alkene into an epoxide.

The steps followed by the given reaction are stated as:

  • First step is the formation of epoxide.
  • Second step is the attack of water to opens the ring.
  • The third step is deprotonation that gives diol product.

(d)

Interpretation Introduction

To determine: The conversion of maleic acid to meso-tartaric acid.

Interpretation: The given question stated that two butenedioic acids are called fumaric acids (trans) and maleic acid (cis) and 2,3Dihydroxybutanedioicacid is called tartaric acid. The given conversion is to be predicted.

Concept introduction: Osmium tetroxide also called osmic acid reacts with alkenes to form cyclic osmate ester. Hydrogen peroxide is used as an oxidizing agent to hydrolyze the osmate ester. The attack of oxygen from osmic acid to the double bond of alkene is from the same side. Thus, they have syn stereochemistry.

Blurred answer
Students have asked these similar questions
Q4: Write organic product(s) of the following reactions and show the curved-arrow mechanism of the reactions. Br MeOH OSO2CH3 MeOH
Provide the correct IUPAC name for the compound shown here. Reset cis- 5- trans- ☑ 4-6- 2- 1- 3- di iso tert- tri cyclo sec- oct but hept prop hex pent yl yne ene ane
Q6: Predict the major product(s) for the following reactions. Note the mechanism (SN1, SN2, E1 or E2) the reaction proceeds through. If no reaction takes place, indicate why. Pay attention to stereochemistry. NaCN DMF Br σ Ilm... Br H Br H H NaCN CH3OH KOtBu tBuOH NaBr H₂O LDA Et2O (CH3)2CHOH KCN DMSO NaOH H₂O, A LDA LDA System

Chapter 8 Solutions

Organic Chemistry (9th Edition)

Ch. 8.7A - Prob. 8.11PCh. 8.7C - Prob. 8.12PCh. 8.7C - Prob. 8.13PCh. 8.7C - a. When (Z)-3-methylhex-3-ene undergoes...Ch. 8.7C - Prob. 8.15PCh. 8.7C - Prob. 8.16PCh. 8.8B - Prob. 8.17PCh. 8.8B - Prob. 8.18PCh. 8.9 - Prob. 8.19PCh. 8.9 - Prob. 8.20PCh. 8.9 - Prob. 8.21PCh. 8.9 - Prob. 8.22PCh. 8.10 - Prob. 8.23PCh. 8.10 - Prob. 8.24PCh. 8.10 - Prob. 8.25PCh. 8.11A - Prob. 8.26PCh. 8.11B - Prob. 8.27PCh. 8.11B - Prob. 8.28PCh. 8.12 - Prob. 8.29PCh. 8.13 - a. Propose a mechanism for the conversion of...Ch. 8.13 - Magnesium monoperoxyphthalate (MMPP) epoxidizes...Ch. 8.13 - Predict the major products of the following...Ch. 8.13 - When 1,2-epoxycyclohexane (cyclohexene oxide) is...Ch. 8.14C - Predict the major products of the following...Ch. 8.14C - Prob. 8.35PCh. 8.15B - Prob. 8.36PCh. 8.15C - Predict the major products of the following...Ch. 8.16A - Prob. 8.38PCh. 8.16A - Prob. 8.39PCh. 8.16B - Prob. 8.40PCh. 8.16B - Prob. 8.41PCh. 8.16C - Prob. 8.42PCh. 8.17B - Prob. 8.43PCh. 8.17B - Prob. 8.44PCh. 8.17B - Show how you would synthesize each compound,...Ch. 8 - Prob. 8.46SPCh. 8 - Prob. 8.47SPCh. 8 - Give the products expected when the following...Ch. 8 - Show how you would make the following compounds...Ch. 8 - Using 1,2-dimethylcyclohexene as your starting...Ch. 8 - Show how you would synthesize each compound using...Ch. 8 - Prob. 8.52SPCh. 8 - Show how you might use olefin metathesis to...Ch. 8 - Prob. 8.54SPCh. 8 - Prob. 8.55SPCh. 8 - Propose mechanisms consistent with the following...Ch. 8 - Prob. 8.57SPCh. 8 - Prob. 8.58SPCh. 8 - Draw a reaction-energy diagram for the propagation...Ch. 8 - Prob. 8.60SPCh. 8 - Prob. 8.61SPCh. 8 - Prob. 8.62SPCh. 8 - Prob. 8.63SPCh. 8 - Prob. 8.64SPCh. 8 - Prob. 8.65SPCh. 8 - Prob. 8.66SPCh. 8 - Prob. 8.67SPCh. 8 - Prob. 8.68SPCh. 8 - Prob. 8.69SPCh. 8 - Prob. 8.70SPCh. 8 - Prob. 8.71SPCh. 8 - Prob. 8.72SPCh. 8 - Prob. 8.73SPCh. 8 - Prob. 8.74SPCh. 8 - Prob. 8.75SPCh. 8 - Prob. 8.76SPCh. 8 - Prob. 8.77SPCh. 8 - Prob. 8.78SPCh. 8 - Prob. 8.79SP
Knowledge Booster
Background pattern image
Chemistry
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
SEE MORE QUESTIONS
Recommended textbooks for you
Text book image
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Text book image
Chemistry for Today: General, Organic, and Bioche...
Chemistry
ISBN:9781305960060
Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Publisher:Cengage Learning