(a)
To determine: The enantiomer of
Interpretation: The enantiomer of
Concept introduction: The Williamson ether synthesis involves displacement of an alkyl halide or tosylate by an alkoxide ion through
(b)
To determine: The best synthesis path for
Interpretation: The best synthesis path for
Concept introduction: The Williamson ether synthesis involves
(c)
To determine: The conversion of
Interpretation: The conversion of
Concept introduction: The Williamson ether synthesis involves
Want to see the full answer?
Check out a sample textbook solutionChapter 11 Solutions
Organic Chemistry (9th Edition)
- 4. A student performed the following sequence of reactions: an oxetane opening, followed by a Williamson ether synthesis; however, the student forgot to write down which alkyl halide they used for the second step of the Williamson ether synthesis, so they do not know what the final product should be. Luckily, a 'H NMR spectrum was obtained for the final product. Determine the product of each step, as well as the alkyl halide that the student added. Draw the mechanism for each step below. MgBr 1. 1. NaH 2. H30* 2. 'H NMR of final product: | = 6 | = 3 | = 2 |= 2 | = 2 3.0 2.5 2.0 1.5 |= 3 | = 2 6 4 2 Mechanism:arrow_forward10) What is the major product of the following reactions? CH3 + HCI H₂O H* ? CH3CO3 H HBr 11) Which is more highly regioselective the addition of HCl to methylenecyclohexane or to 1- methylcyclohexene? Explain. What product(s) is/are formed when the following compound react with ozone and then with dimethyl sulfide (i.e. ozonolysis)? a) b)arrow_forwardBe sure to answer all parts. Synthesize the following compound from cyclohexanol, ethanol, and any other needed reagents. он Part 1 out of 2 Preparation of organometallic reagent: B CH3CH2OH CH3CH2MGB. draw structure... Draw the intermediate product above and select the correct reagent for A. NaBr O MgBr2 Br2 HBr Select the correct reagent for B. O Mgo O Mgl, O Mg O MgBr2 Next partarrow_forward
- Draw the major organic product of the reaction. Indicate the stereochemistry via wedge/dash bonds, including explicit H and D atoms, at the stereogenic center. Omit byproducts such as salts or methanol. Br NaOCH CH OH Harrow_forwardWhy do cis-1-bromo-2-ethylcyclohexane and trans-1-bromo-2-ethylcyclohexane form different major products when they undergo an E2 reaction?arrow_forward3. Substitution and Elimination. Consider the 2° alkyl halide shown below. Draw all major product(s) if it were to be treated with the following reagents. Be sure to consider stereochemistry and include structures of stereoisomers if present. H₂O Na OCH3. Acetonitrile CH3 ~Ire H3C- CH3 -OK* H3CS Na Acetonitrile Brarrow_forward
- The reaction of tert-butyl cyclopentyl ether with trifluoroacetic acid is shown below. Explain what kind of reaction this is (SN1, SN2, E1, E2...) and show the mechanism for this transformation.arrow_forward1) Draw the complete electron-pushing arrow mechanism for the following reductions. Explain, using resonance contributors (structures), the regiochemistry that results in each case. OMe Na, MeOH ? NH3 CHO Na, MeOH ? NH3arrow_forwardCitral is industrially synthesized from the enol ether of 3-methylprop-3-enal and 3,3- dimethylallylic alcohol (the starting material shown below). So right when you thought that all of that pericyclic stuff is just some esoteric nonsense, here they are, sigmatropic rearrangements in real life action. da a) Redraw the structures of the starting material and the intermediate, so that you have an easier time to indicate with curved arrows how the sigmatropic rearrangements (yes, there are two consecutive ones) are proceeding. b) Name the two sigmatropic rearrangements. heat heat الله citral Harrow_forward
- 1. Predict whether the following reactions are likely to proceed by an E1 or E2 mechanism. 2. Explain each prediction. Br KOH CH₂CH₂OH Br CH₂CH₂OH Br 4 Br H₂O of S-Bassuo CH₂0-/CH₂OHarrow_forwardTwo possibilities for a Wittig synthesis of the compound below involve using: 1) cyclohexanone and ethyl bromide or 2) bromocyclohexane and ethanal. Is either route better, and if so, why is one superior? Be specific and explain where the difficulty lies for the inferior route - CH3 -Harrow_forwardFor each of the following reactions, draw the major elimination product; if the product can exist as stereoisomers, indicate which stereoisomer is obtained in greater yield. a. (R)-2-bromohexane + high concentration of CH3O- b. (R)-3-bromo-3-methylhexane + CH3OH c. trans-1-chloro-2-methylcyclohexane + high concentration of CH3O- d. trans-1-chloro-3-methylcyclohexane + high concentration of CH3O- e. 3-bromo-3-methylpentane + high concentration of CH3CH2O- f. 3-bromo-3-methylpentane + CH3CH2OHarrow_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