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Concept explainers
a) NaH then CH3I
Interpretation:
The product formed when estradiol reacts with NaH and then with CH3I is to be given.
Concept introduction:
When treated with NaH and CH3I, The hydrogen of -OH group in alcohols and phenols is replaced by methyl group.
To give:
The product formed when estradiol reacts with NaH and then with CH3I.
b) CH3COCl, pyridine
Interpretation:
The product formed when estradiol reacts with CH3COCl in pyridine is to be given.
Concept introduction:
When treated with CH3COCl in pyridine, the hydrogen of -OH group in alcohols and phenols is replaced by acetyl group.
To give:
The product formed when estradiol reacts with CH3COCl in pyridine.
c) Br2, FeBr3
Interpretation:
The product formed when estradiol reacts with Br2, FeBr3 to be given.
Concept introduction:
Phenols undergo electrophilic substitution reaction (bromination) when treated with Br2, FeBr3 in the ortho and para positions.
To give:
The product formed when estradiol reacts with Br2, FeBr3.
d) Dess-Martin periodinane
Interpretation:
The product formed when estradiol reacts with Dess-Martin periodinate is to be given.
Concept introduction:
Secondary alcohols are oxidized to
To give:
The product formed when estradiol reacts with Dess-Martin periodinate.
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Chapter 27 Solutions
OWLv2 with Student Solutions Manual eBook, 4 terms (24 months) Printed Access Card for McMurry's Organic Chemistry, 9th
- Please complete these blanks need that asaparrow_forwardNitration of Methyl Benzoate: 1. Predict the major product for the reaction below AND provide a mechanism. Include ALL resonance structures for the intermediate. C(CH3)3 NO₂* ? 2. Assuming the stoichiometry is 1:1 for the reaction above, what volume of concentrated nitric acid would be required to mononitrate 0.50 grams of the compound above? What product(s) might you expect if you nitrated phenol instead of methyl benzoate? Explain your reasoning. What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What other impurities are present in your product and how do you know?arrow_forwardSodium Borohydride Reduction (continued on the next page): 1. Draw the product of each of the reactions below and give the formula mass to the nearest whole number. ? (1) NaBH (2) acid (1) NaBD4 (2) acid ? 2. In mass spectra, alcohols typically break as shown in equation 8 in chapter 11 (refer to your lab manual). The larger group is generally lost and this gives rise to the base peak in the mass spectrum. For the products of each of the reactions in question # 1, draw the ion corresponding to the base peak for that product and give its mass to charge ratio (m/z). 3. Given the reaction below, calculate how many mg of 1-phenyl-1-butanol that can be produced using 31 mg NaBH4 and an excess of butyrophenone. 4. + NaBH4 OH (after workup with dilute HCI) What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What other impurities are present in your product and how do you know?arrow_forward
- Aspirin from Wintergreen: 1. In isolating the salicylic acid, why is it important to press out as much of the water as possible? Write a step-by-step mechanism for the esterification of salicylic acid with acetic anhydride catalyzed by concentrated H₂SO4. 3. Calculate the exact monoisotopic mass of aspirin showing your work. What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What other impurities are present in your product and how do you know?arrow_forwardSynthesis of Ibuprofen-Part 1: 1. What characteristic absorption band changes would you expect in the IR spectrum on going from p-isobutylacetophenone to 1-(4-isobutylphenyl)-ethanol and then to 1-(4-isobutylphenyl)-1-choroethane as you did in the experiment today? Give approximate wavenumbers associated with each functional group change. Given that the mechanism of the chlorination reaction today involves formation of a benzylic carbocation, explain why the following rearranged product is not formed. محرم محمد 3. Why do we use dilute HCl for the first step of the reaction today and concentrated HCI for the second step? What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What other impurities are present in your product and how do you know?arrow_forwardAssign only the C NMRarrow_forward
- 2. Identify the reagents you would need to achieve the following. You may need to consider using a protecting group. HO 1. 2. 3. 4. 5. OH Br HOarrow_forwardBeF2 exists as a linear molecule. Which kind of hybrid orbitals does Be use in this compound? Use Orbital Diagrams to show how the orbitals are formed. (6)arrow_forwardPlease answer the questions and provide detailed explanations as well as a drawing to show the signals in the molecule.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
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