
Concept explainers
Interpretation:
It should be determined that the given [1, 7] sigmatropic rearrangement involves whether suprafacial or antarafacial rearrangement.
Concept introduction:
In a sigmatropic reaction “ one new sigma-bond is formed as another breaks.”
Sigmatropic rearrangement reactions are named with digits. For example a [1, 3] sigmatropic rearrangement describe a reaction in which the residue migrates from position 1 to position 3.
Migration of carbon and hydrogen will occur in a sigmatropic rearrangement reaction.
When hydrogen migrates in a sigmatropic rearrangement, the s orbital of the hydrogen is partially bonded to both the migration origin and the migration terminus in the transition state.
Migration of hydrogen in suprafacial and antarafacial rearrangement can be represented as follows,
Migration of carbon occurs through two ways because it has a two lobed p orbital. Carbon can simultaneously interact with the migration origin and the migration terminus using one lobe of its p orbital. Migration of carbon in suprafacial and antarafacial rearrangement can be represented as follows,
Carbon migrating with one lobe of its p orbital interacting
Carbon migrating with both lobe of its p orbital interacting

Trending nowThis is a popular solution!

Chapter 28 Solutions
EBK ORGANIC CHEMISTRY
- 5. Drawn the structure of the compound (molecular formula C12H16) with the longest λmax in its UV-vis spectrum.arrow_forwardUse solubility rules to complete balance molecular equations, and provide total and net ionic equations.arrow_forwardUse solubility rules to provide balance molecular equation, total, and net ionic equationarrow_forward
- Use solubility rules to provide balance molecular equation, total, and net ionic equationarrow_forwardBr HO ? HO ✓ OHarrow_forwardUse the literature Ka value of the acetic acid, and the data below to answer these questions. Note: You will not use the experimental titration graphs to answer the questions that follow. Group #1: Buffer pH = 4.35 Group #2: Buffer pH = 4.70 Group #3: Buffer pH = 5.00 Group #4: Buffer pH = 5.30 Use the Henderson-Hasselbalch equation, the buffer pH provided and the literature pKa value of acetic acid to perform the following: a) calculate the ratios of [acetate]/[acetic acid] for each of the 4 groups buffer solutions above. b) using the calculated ratios, which group solution will provide the best optimal buffer (Hint: what [acetate]/[acetic acid] ratio value is expected for an optimal buffer?) c) explain your choicearrow_forward
- How would you prepare 1 liter of a 50 mM Phosphate buffer at pH 7.5 beginning with K3PO4 and 1 M HCl or 1 M NaOH? Please help and show calculations. Thank youarrow_forwardDraw the four most importantcontributing structures of the cation intermediate thatforms in the electrophilic chlorination of phenol,(C6H5OH) to form p-chlorophenol. Put a circle aroundthe best one. Can you please each step and also how you would approach a similar problem. Thank you!arrow_forwardA 100mM lactic acid/lactate buffer was found to have a lactate to lactic acid ratio of 2 and a pH of 4.2. What is the pKa of lactic acid? Can you please help show the calculations?arrow_forward
- Using line angle formulas, draw thestructures of and name four alkanes that have total of 7carbons, one of which is tertiary.Please explain this in detail and can you also explain how to approach a similar problem like this as well?arrow_forwardUsing dashed line wedge projections drawthe indicated compounds and indicate whether thecompound you have drawn is R or S.(a) The two enantiomers of 2-chlorobutane. Can you please explain your steps and how you would approach a similar problem. Thank you!arrow_forward5) There are no lone pairs shown in the structure below. Please add in all lone pairs and then give the hybridization scheme for the compound. (8) 10,11 7) 1.2.3 H 4 | 14 8) COC 12 13 H 16 15 H7 9) - 5.6 C 8 H 10) H 1). 2) 3)_ 11) 12) 13) 4)_ 14) 5) 15) 16) 6)arrow_forward
- Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage LearningOrganic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning


