Interpretation:
The way by which the given synthesis is being accomplished has to be shown and explanation for the stereoselective synthesis of 10-trans-12-cis isomer.
Concept introduction:
Wittig Reaction: It is an organic reaction where an
Non-stabilized ylide (having electron donating group on negatively charged carbon) gives Z-isomer whereas stabilized ylide (having electron withdrawing group on negatively charged carbon) gives E-isomer.
Non–stabilized ylide (having electron donating group on negatively charged carbon) gives Z–isomer whereas stabilized ylide (having electron withdrawing group on negatively charged carbon) gives E–isomer.
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Chapter 18 Solutions
Organic Chemistry
- Following is the structure of miconazole, the active antifungal agent in a number of over-the-counter preparations, including Monistat, that are used to treat vaginal yeast infections. One of the compounds needed for the synthesis of miconazole is the trichloro derivative of toluene shown on its right. (a) Show how this derivative can be synthesized from toluene. (b) How many stereoisomers are possible for miconazole?arrow_forward-Ocimene is a pleasant-smelling hydrocarbon found in the leaves of certain herbs. It has the molecular formula C10H16 and a UV absorption maximum at 232 nm. On hydrogenation with a palladium catalyst, 2,6-dimethyloctane is obtained. Ozonolysis of -ocimene, followed by treatment with zinc and acetic acid, produces the following four fragments: (a) How many double bonds does -ocimene have? (b) Is -ocimene conjugated or nonconjugated? (c) Propose a structure for -ocimene. (d) Write the reactions, showing starting material and products.arrow_forwardFollowing is the structural formula of Surfynol, a defoaming surfactant. Describe the synthesis of this compound from acetylene and a ketone. How many stereoisomers are possible for Surfynol?arrow_forward
- All rearrangements we have discussed so far have involved generation of an electron-deficient carbon followed by a 1,2-shift of an atom or a group of atoms from an adjacent atom to the electron-deficient carbon. Rearrangements by a 1,2-shift can also occur following the generation of an electron-deficient oxygen. Propose a mechanism for the acid-catalyzed rearrangement of cumene hydroperoxide to phenol and acetone.arrow_forwardPropose a series of reactions that would convert the provided starting material into the given product. The synthesis will take more than one step. For each reaction you use, show the reagents you would use and the product of that step. In each step, your desired product should be formed as the major product. Assume chiral products are formed as racemic mixtures. Your reactions should give the correct diastereomer. All carbons in the final products must come from the provided starting materials. In addition to the provided starting materials, you may use any reagents we have discussed. Hint, you’ll need to convert the starting materials into functional groups that you can connect together. I need help with this practice problem, thank you!arrow_forwardConsider the substitution reaction that takes place when (R)-3-bromo-3-methylhexane is treated with sodium methoxide. Deduce the mechanism of this reaction working step by step. Write all possible products showing the stereochemistry.arrow_forward
- A compound of formula C6H10O2 shows only two absorptions in the proton NMR: a singlet at 2.67 ppm and a singlet at2.15 ppm. These absorptions have areas in the ratio 2:3. The IR spectrum shows a strong absorption at 1708 cm-1. Proposea structure for this compound.arrow_forwardMuscalure is the sex attractant of the common housefly. Flies are lured to traps filled with bait thatcontain muscalure and an insecticide. Eating the bait is fatal. How could you synthesize muscalure using 1-bromopentane as one of the starting materials?arrow_forwardThe 1H and 13C NMR spectra of compound A, C8H9Br are shown below. Answer the following questions. 1(a) Degree of the unsaturation of this compound is = , 1(b) The derived unsaturation number indicates that compound has ............= 1(c) Two peaks in between 6.5 - 8.0 δ indicate that compound is= 1(d) According to the splitting pattern of the peak at 1.20 δ and 2.58 δ indicates that compound has a .................. group= 1(e) According to the 1H NMR spectrum the number of nonequivalent aromatic proton sets in the compound = 1(f) According to the 13C NMR, the number of nonequivalent carbons in the compound is = 1(g) According to your answer in Q 1(f) the compound has a plane of symmetry Yes or NO = 1(h) The IUAC name for this unknown compound isNOT TOO SURE ABOUT MY ANSWERS, PLEASE CORRECT ME IF I'M WRONGarrow_forward
- Compound A has the formula C9H19Cl. B is a C9H19Br compound.A and B undergo base-promoted E2 elimination to give the same alkene C as the major product as well as different minor products.C reacts with one molar equivalent of hydrogen in the presence of a palladium catalyst to form 2,6-dimethylheptane.Addition of HCl to C yields A as the major product.Propose structures for A and B.arrow_forwardConsider the tetracyclic aromatic compound drawn below, with rings labeled as A, B, C, and (a) Which of the four rings is most reactive in electrophilic aromatic substitution? (b) Which of the four rings is least reactive in electrophilic aromatic substitution? (c) What are the major produces) formed when this compound is treated with one equivalent of Br2?arrow_forwardThe endiandric acids comprise a group of unsaturated carboxylic acids isolated from a tree that grows in the rainforests of eastern Australia. The methyl esters of endiandric acids D and E have been prepared from polyene Y by a series of two successive electrocyclic reactions: thermal ring closure of the conjugated tetraene followed by ring closure of the resulting conjugated triene. (a) Draw the structures (including stereochemistry) of the methyl esters of endiandric acids D and E. (b) The methyl ester of endiandric acid E undergoes an intramolecular [4 + 2] cycloaddition to form the methyl ester of endiandric acid A. Propose a possible structure for endiandric acid A.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning