Concept explainers
Interpretation:
Accomplishment of each of the given transformations is to be shown.
Concept introduction:
Swern Oxidation converts primary and secondary alcohols into
Reduction of
Chromic acid oxidation: Oxidation of primary alcohols to aldehydes and use of hydronium (aqueous medium) to further oxidize the aldehydes to
Pyridinium Chlorochromate (PPC): PPC is formed from pyridine, hydrochloric acid and chromium oxide. This allows for controlled oxidation since this reaction takes place in anhydrous conditions.
Potassium Permanganate: Potassium permanganate is a strong oxidizing agent. It converts the primary alcohols and aldehydes to their corresponding carboxylic acids. It converts secondary alcohols to ketones. This is not a controlled reaction since the reaction occurs in aqueous medium.
When an oxidation takes place, the hydrogen atom attached to the oxygen atom is removed to form aldehydes from alcohols, or to form carboxylic acids from aldehydes. Compounds with no hydrogen attached to oxygen cannot be oxidized using Swern oxidation. Examples of such compounds are tertiary alcohols and ethers.
Want to see the full answer?
Check out a sample textbook solutionChapter 12 Solutions
ORGANIC CHEMISTRY (LL) W/WILEYPLUS NEXT
- Using cyclohexane as your starting material, show how you would synthesize each of the following compounds. (Onceyou have shown how to synthesize a compound, you may use it as the starting material in any later parts of this problem.)(a) bromocyclohexanearrow_forwardUsing cyclohexane as your starting material, show how you would synthesize each of the following compounds. (Onceyou have shown how to synthesize a compound, you may use it as the starting material in any later parts of this problem.)(a) bromocyclohexane (b) cyclohexenearrow_forwardPractice Problem 13.36b Problem 13.34 outlines a general method for the preparation of cis- or trans-disubstituted epoxides. Using that method, identify what reagents you would use to prepare the following epoxide from acetylene: H" 'Et The transformation above can be performed with some reagent or combination of the reagents listed below. Give the necessary reagent(s) in the correct order, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide just one answer. A B C D DMP or PCC На, Pt EtBr PHCH2BR E F H H2SO4, H20, HgSO4 МСРВА (RCO3зН) Na, NH3 (/) H2, Lindlar's cat. I K TSCI, py PhBr NANH2 1) EtMgBr; 2) H30+arrow_forward
- 3) Propose suitable reagent(s) to accomplish the following transformations. (a) (b) Br N OH orarrow_forwardUsing your reaction roadmap as a guide, show how to convert cyclohexanol into racemic trans-1,2-cyclohexanediol. (1) (2) (3) OH OH trans-1,2-cyclohexanediol (racemic) Submit Answer Suggest reagents and experimental conditions for each step in this synthesis. From the choices provided, suggest appropriate reagents for each step. More than one reagent may be necessary. Use the minimum number of steps possible. Enter your answer as a letter, or a series of letters, in the order necessary to bring about the steps shown. Reagents: (c) ethylene oxide OH "OH (a) CH3O Na+, CH, OH (d) H₂SO4, H₂O (b) OsO4, H₂O2 Retry Entire Group OH (e) m-chloroperoxybenzoic acid (mCPBA) (f) pyridinium chlorochromate (PCC) + 9 more group attempts remaining 2 (9) H₂SO4 (anhydrous) (j) Na, NH3 (1) (h) NaOH (k) NBS, heat (i) PBr3 (N-bromosuccinimide) Previous Nextarrow_forward(c) Answer each of the questions below that relate to acetophenone: Xo (i) (ii) (iii) Draw the structure of the enol form of acetophenone. Give a stepwise mechanism for the conversion of acetophenone into its enol form. Show how each of the three compounds A, B and C below can be prepared from acetophenone. Explain clearly what reactants/reagents would be required in each case. odocor A B Br Carrow_forward
- Using cyclohexane as your starting material, show how you would synthesize each of the following compounds. (Onceyou have shown how to synthesize a compound, you may use it as the starting material in any later parts of this problem.)(a) bromocyclohexane (b) cyclohexene (c) ethoxycyclohexane(d) 3-bromocyclohex-1-ene (e) cyclohexa-1,3-diene (f) cyclohexanolarrow_forwardUsing cyclohexane as your starting material, show how you would synthesize each of the following compounds. (Onceyou have shown how to synthesize a compound, you may use it as the starting material in any later parts of this problem.)(a) bromocyclohexane (b) cyclohexene (c) ethoxycyclohexane(d) 3-bromocyclohex-1-enearrow_forwardPractice Problem 12.42b Predict the product and draw a mechanism for the following reaction: NABH, MEOH 12.42b Draw the major organic product.arrow_forward
- Show how the following ethers might be synthesized using (1) alkoxymercuration–demercuration and (2) the Williamson synthesis. (When one of these methods cannot beused for the given ether, point out why it will not work.)(a) 2-methoxybutane (b) ethyl cyclohexyl etherarrow_forwardPredict the product(s) and show the complete electron-pushing mecha- nism for each of the following dissolving metal reductions. (a) H3CC=CCH₂CH3 (b) (c) CECH 1844 Li NH3 ND3 C=C—CH3 NH3arrow_forwardUsing cyclooctyne as your starting material, show how you would synthesize the following compounds. (Once you haveshown how to synthesize a compound, you may use it as the starting material in any later parts of this problem.)(a) cis-cyclooctene (b) cyclooctane (c) trans-1,2-dibromocyclooctanearrow_forward
- 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