1. Below are two potential methods for preparing the same ether, but only one of them is successful. Identify and explain the successful approach. NaOMe CH3I Χ ONa X
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- Provide the structure(s) of the expected major organic product of the reaction shown. 1) Disiamylborane 2) H₂O₂, NaOH OI O II ||| O IV OV CH3CH₂C(CH3)2C=CH OH OH xx xo IVBelow are two potential methods for preparing the same ether, but only one of them is successful. Identify the successful approach and briefly explain your choice. ONa NaOMe CH3INonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium with their conjugated , -unsaturated isomers. Propose a mechanism for this isomerization.
- 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.Treatment of cis-4-bromocyclohexanol with HO− affords compound Aand cyclohex-3-en-1-ol. Treatment of trans-4-bromocyclohexanol under the same conditions forms compound B and cyclohex-3-en-1-ol. A and Bcontain different functional groups and are not isomers of each other.Propose structures for A and B and offer an explanation for theirformation.A solution of acetone [(CH3)2C=O] in ethanol (CH3CH2OH) in the presence of a trace of acid was allowed to stand for several days, and a new compound of molecular formula C7H16O2 was formed. The IR spectrum showed only one major peak in the functional group region around 3000 cm−1, and the 1H NMR spectrum is given here. What is the structure of the product?
- Provide reagents and conditions to produce the products indicated. CH3 H3C. CH3 O H3C Br H3C° H3C' HO, CH3 HO но H3C mo H3C° HO, H3C 180 .CH3Provide reagents/conditions to accomplish the following transformations. Label each reaction type in the steps you provide. OEt MeO OMe3A Complete the reactions below. H₂SO4/H₂O HgSO4 A NaBH4 EtOH B лH₂SO4 C
- Give the major product or reagent represented by letters A-H: i) NaBH4 A i) MeO ii) H20 `NO2 Mg/Ether ii) RO OR KMNOJ H® D `OH РСС ii) CH,C2 НeatTreatment of cis-4-bromocyclohexanol with HO– affords compound A and cyclohex-3-en-1-ol. Treatment of trans-4- bromocyclohexanol under the same conditions forms compound B and cyclohex-3-en-1-ol. A and B contain different functional groups and are not isomers of each other. Propose structures for A and B and offer an explanation for their formation.Provide reagents and conditions with mechanisms to produce the products indicated. CH3 OH HO HO CH3 HO OH H3C OH OH HO
