Concept explainers
Interpretation:
To complete each of the hydroboration steps by adding the curved arrows, when borane add to propene to produce two different products, and to indicate the pertinent steric repulsion that is present in each reaction, as well as the partial charges that develop in the transition state, similar to Equations 12-36 and 12-37, and to determine which reaction is favored.
Concept introduction:
Hydroboration is stereospecific with the H and
In the transition states a partial positive charge appears on the C atom that has a partial bond to H. This is because the step is driven by the formation of a bond between the electron-rich alkene and the electron-poor B atom, so the C-B bond is formed to a greater extent in the transition state than the C-H bond. The transition state is more stable when the
Want to see the full answer?
Check out a sample textbook solutionChapter 12 Solutions
ORGANIC CHEM. PRIN AND MECHANISM LL+ AC
- Curved arrows are used to illustrate the flow of electrons. Using the provided starting and product structures, draw the curved electron- pushing arrows for the following reaction or mechanistic step(s). Be sure to account for all bond-breaking and bond-making steps. 0°• 1 H Drawing Arrows NaOH, H₂O heat :I:0 > H. Na Ⓒ :O:arrow_forwardComplete the mechanism of hydration of alkene below. Please follow curved arrows to predict the resulting structures in each step Step 1 of hydration of 2-methyl-1-propene (Note that the most stable carbocation is formed here) Step 2 of hydration of 2-methyl-1-propene(Note that the most stable carbocation is formed here) Step 3 of hydration of 2-methyl-1-propenearrow_forwardCurved arrows are used to illustrate the flow of electrons. Using the provided starting and product structures, draw the curved electron-pushing arrows for the following reaction or mechanistic steps. Be sure to account for all bond- breaking and bond-making steps. HH H H H H :0 Select to Add Arrows H H H H I I H3O+ heat H3O+ heat I HH H H3O+ Select to Add Arrows heat H HH H H H :0: HH H Select to Add Arrows H I I H HIarrow_forward
- For each of the following, write the major product(s) and then draw out each step in the mechanism using curved arrows. Show ALL lone pair electrons and formal charges. Redraw ALL molecules as to show explicitly ALL bonds being broken or formed. Identify the molecular orbital (HOMO) of the nucleophile and the molecular orbital (LUMO) of electrophile involved in the nucleophilic attack. MO diagrams are not necessary..arrow_forwardPredict the product or starting material of the following alkene addition reactions. Remember, Hydride shifts are possible if/when a more stable carbocation can exist! Put your answers (organic products only) in the indicated boxes.arrow_forwardDraw the major 1,2- and 1,4-addition products obtained in the reaction shown. Assume that both are derived from the most stable carbocation intermediate. + HCI • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • If the 1,2- and 1,4- addition products are the same due to symmetry, only draw one structure. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. ● Separate multiple products using the + sign from the drop-down menu.arrow_forward
- Curved arrows are used to illustrate the flow of electrons. Using the provided starting and product structures, draw the curved electron-pushing arrows for the following reaction or mechanistic step(s). Be sure to account for all bond-breaking and bond-making steps. Then draw the organic product of the reaction. Include all lone pairs in the structures. Ignore inorganic byproducts and + counterions. Drawing Arrows NaNH2 Select to Draw Product H H I I O:Z: + S :O: H Undo H Na+ EP Resetarrow_forwardShown below is a carbocation intermediate in an electrophilic addition reaction of HCl with an alkene. For the conformation shown, select each hydrogen whose bond to carbon is aligned for effective hyperconjugation with the vacant p orbital on the positively charged carbon. Each adjacent carbon will have only one C-H bond so aligned. I need to click on the Hydrogens which then highlights the clicked hydrogens in blue. Much help needed. There are hydrogens and carbons shown.arrow_forwardCurved arrows are used to illustrate the flow of electrons. Follow the curved arrows and draw the intermediate and product in this reaction sequence. Problem 19 of 50 Submit Include all lone pairs and charges as appropriate. Ignore any inorganic byproducts. H-Br: Select to HBr HRr Select to Draw :Br: Brarrow_forward
- TROVIOW Topicaj (References) Draw the major organic product of the reaction shown below. HO, NANH2 You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • Include cationic counter-ions, e.g., Na" in your answer, but draw them in their own sketcher. (Review Top Draw the major organic product of the reaction shown below. OH K2Cr207 H2SO4, H20 • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one.arrow_forwardCurved arrows are used to illustrate the flow of electrons. Using the provided starting and product structures, draw the curved electron-pushing arrows for the following reaction or mechanistic steps. Be sure to account for all bond-breaking and bond-making steps. Br Select to Add Arrows Br. H I I H C Select to Add Arrows H H : Br: O H : Br: O Select to Add Arrows I I I I Iarrow_forwardCurved arrows are used to illustrate the flow of electrons. Using the provided starting and product structures, draw the curved electron-pushing arrows for the following reaction or mechanistic step(s). Be sure to account for all bond-breaking and bond-making steps. · Select to Add Arrows I Brh H Br. H 0. H Br2 H₂O Br2 = H₂O Br: O Br HOH Select to Add Arrows I Br2 H₂O Br H. Br: OH Select to Add Arrows Iarrow_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