Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
expand_more
expand_more
format_list_bulleted
Question
Chapter 12, Problem 12.76P
Interpretation Introduction
Interpretation: Among the given alcohols, the one which gets oxidized rapidly by
Concept introduction: The oxidation by chromium ion favors the oxidation of sterically hindered alcohol as it leads to the relief of steric strain due to the transition from
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
Axial alcohols are oxidized faster than equatorial alcohols by PCC andother Cr6+ oxidants. Which OH group in each compound is oxidizedfaster?
Many insects utilize cyclic ketal structures as pheromones such
as the structure shown below. The biosynthetic pathway
involves the cyclization of this acetal from the straight chain
structure. Draw the straight chain structure that could be used
to form this acetal. Use wedges and dashes to correctly depict
the stereochemistry.
H3C-
>
Cr(VI) compounds are common reagents for the oxidation of alcohols. Primary alcohols are oxidized to carboxylic acids and secondary alcohols are oxidized to ketones. The mechanism involves a reaction similar to the E2 elimination, whereby a C=O double bond is formed with a reduced Cr(IV) compound as the leaving group.Draw curved arrows to show the movement of electrons in this step of the mechanism.
Chapter 12 Solutions
Organic Chemistry
Ch. 12 - Prob. 12.1PCh. 12 - Prob. 12.2PCh. 12 - Prob. 12.3PCh. 12 - Prob. 12.4PCh. 12 - Prob. 12.5PCh. 12 - Given that syn addition of H2 occurs from both...Ch. 12 - Compound Molecular formula before...Ch. 12 - Draw the products formed when triacylglycerol A is...Ch. 12 - Prob. 12.9PCh. 12 - Prob. 12.10P
Ch. 12 - Problem 12.11 (a) Draw the structure of a compound...Ch. 12 - Prob. 12.12PCh. 12 - Prob. 12.13PCh. 12 - Prob. 12.14PCh. 12 - Prob. 12.15PCh. 12 - Prob. 12.16PCh. 12 - Prob. 12.17PCh. 12 - Problem 12.18 Draw the products formed when both...Ch. 12 - Prob. 12.19PCh. 12 - Prob. 12.20PCh. 12 - Prob. 12.21PCh. 12 - Prob. 12.22PCh. 12 - Prob. 12.23PCh. 12 - Problem 12.24 Draw the organic products in each of...Ch. 12 - Prob. 12.25PCh. 12 - Prob. 12.26PCh. 12 - Problem 12.27 Draw the products of each Sharpless...Ch. 12 - Prob. 12.28PCh. 12 - 12.29 Draw the products formed when A is treated...Ch. 12 - Prob. 12.30PCh. 12 - 12.31 Devise a synthesis of the following compound...Ch. 12 - Label each reaction as oxidation, reduction, or...Ch. 12 - Prob. 12.33PCh. 12 - Prob. 12.34PCh. 12 - Prob. 12.35PCh. 12 - Prob. 12.36PCh. 12 - 12.37 Stearidonic acid (C18H28O2) is an...Ch. 12 - Draw the organic products formed when cyclopentene...Ch. 12 - Prob. 12.39PCh. 12 - Draw the organic products formed when allylic...Ch. 12 - Draw the organic products formed in each reaction...Ch. 12 - Draw the organic products formed in each reaction....Ch. 12 - Prob. 12.43PCh. 12 - Prob. 12.44PCh. 12 - Prob. 12.45PCh. 12 - What alkene is needed to synthesize each 1,2-diol...Ch. 12 - Prob. 12.47PCh. 12 - Draw the products formed after Steps 1 and 2 in...Ch. 12 - Prob. 12.49PCh. 12 - Prob. 12.50PCh. 12 - Prob. 12.51PCh. 12 - What alkyne gives each set of products after...Ch. 12 - Prob. 12.53PCh. 12 - Prob. 12.54PCh. 12 - Prob. 12.55PCh. 12 - 12.54 An unknown compound A of molecular formula ...Ch. 12 - 12.55 DHA is a fatty acid derived from fish oil...Ch. 12 - Prob. 12.58PCh. 12 - Prob. 12.59PCh. 12 - 12.58 Epoxidation of the following allylic alcohol...Ch. 12 - What allylic alcohol and DET isomer are needed to...Ch. 12 - Devise a synthesis of each hydrocarbon from...Ch. 12 - Prob. 12.63PCh. 12 - 12.62 It is sometimes necessary to isomerize a cis...Ch. 12 - Prob. 12.65PCh. 12 - Prob. 12.66PCh. 12 - Prob. 12.67PCh. 12 - Prob. 12.68PCh. 12 - Devise a synthesis of each compound from the...Ch. 12 - Devise a synthesis of each compound from acetylene...Ch. 12 - Prob. 12.71PCh. 12 - Prob. 12.72PCh. 12 - Prob. 12.73PCh. 12 - Prob. 12.74PCh. 12 - Prob. 12.75PCh. 12 - Prob. 12.76PCh. 12 - 12.72 Draw a stepwise mechanism for the following...Ch. 12 - Prob. 12.78PCh. 12 - Prob. 12.79PCh. 12 - Prob. 12.80PCh. 12 - 12.75 Sharpless epoxidation of allylic alcohol X...
Knowledge Booster
Similar questions
- Identify the most important aldehyde and ketone from Section 14.4 on the basis of amount used, and list at least one characteristic for each that contributes to its usefulness.arrow_forwardAldehydes and ketones react with one molecule of an alcohol to form compounds called hemiacetals, in which there is one hydroxyl group and one ether-like group. Reaction of a hemiacetal with a second molecule of alcohol gives an acetal and a molecule of water. We study this reaction in Chapter 16. Draw structural formulas for the hemiacetal and acetal formed from these reagents. The stoichiometry of each reaction is given in the problem.arrow_forward17-60 1-Propanol can be prepared by the reduction of an aldehyde, but it cannot be prepared by the acid catalyzed hydration of an alkene. Explain why it cannot be prepared from an alkene.arrow_forward
- Arrange these compounds in order of increasing boiling point (values in C are 42, 24, 78, and 118). (a) CH3CH2OH (b) CH3OCH3 (c) CH3CH2CH3 (d) CH3COOHarrow_forwardExplain the process of Conversion of hexan-2-ol to other compounds ?arrow_forwardRank the following alcohols in order of increasing ease of acid-catalyzed dehydration. Provide the structure of the dehydration product (alkene) from each alcohol. OH OH 3 1 a OHarrow_forward
- Which of the following statements is true about the organic product of this reaction if the reaction occurs at the Si face of the ketone? 1. Mg, Br diethyl ether product 2. H3O* O The reaction mechanism involves the formation of a carbocation intermediate. O The product has a chirality centre (stereocentre) of S configuration. The product contains 11 carbon atoms, 5 of which are sp2 hybridized. O The product is a secondary alcohol. O The degree of unsaturation of the product is 4. MacBook Pro Q在百度中搜索arrow_forwardwhy do tertiary alcohols ionize readily in acidic mediaarrow_forward2arrow_forward
- What reducing agent can selectively reduce aldehydes, but not esters? KMnO4 OsO4 LiAlH4 NaBH4 What kind of compound is made when an aldehyde is treated with a Grignard reagent? Carboxylic acid Primary alcohol Secondary alcohol Tertiary alcoholarrow_forwardComplete the following steps of the reaction using proper stereochemistry, using all the wedge and dash diagrams and also state if the resulting solutions of the products are optically active.arrow_forward5 In the Fischer esterification reaction, a carboxylic acid reacts with an excess of alcohol in acidic conditions to form an ester. During the reaction the sp2 hybridized carbonyl carbon of the acid forms an sp3 hybridized intermediate before returning to sp² hybridization in the product. Draw the structure of the neutral sp³ hybridized intermediate and the ester product in the reaction between pentanoic acid and n-propanol. pentanoic acid + n-propanol Draw the neutral sp³ intermediate. Select Draw Templates More C H O H* propanol neutral sp³ intermediate Erase Draw the ester product. ester product Select Draw Templates More C H O Erasearrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage LearningChemistry & Chemical ReactivityChemistryISBN:9781337399074Author:John C. Kotz, Paul M. Treichel, John Townsend, David TreichelPublisher:Cengage Learning
- Chemistry & Chemical ReactivityChemistryISBN:9781133949640Author:John C. Kotz, Paul M. Treichel, John Townsend, David TreichelPublisher:Cengage LearningChemistry for Today: General, Organic, and Bioche...ChemistryISBN:9781305960060Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. HansenPublisher:Cengage LearningOrganic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Cengage Learning
Chemistry & Chemical Reactivity
Chemistry
ISBN:9781337399074
Author:John C. Kotz, Paul M. Treichel, John Townsend, David Treichel
Publisher:Cengage Learning
Chemistry & Chemical Reactivity
Chemistry
ISBN:9781133949640
Author:John C. Kotz, Paul M. Treichel, John Townsend, David Treichel
Publisher:Cengage Learning
Chemistry for Today: General, Organic, and Bioche...
Chemistry
ISBN:9781305960060
Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning