Question

[Review Topics References Specify both the alcohol starting material and the reagents you would use in each step in a synthesis of the compound shown. If the synthesis requires only two stepsenter one for step 3 Alcohol Starting Materials 1. methanol 2. ethanol 3. 1-propanol 4.2.propanol 5. cyclohexanol Reagents available 3. LAH b. H,SO, e.HCI d. HB SOCI PB CrO, H, SOHO . NAH LCH, MgBr, then H, O J.CH,CH, MgBr; then H.O' k.CH,CH, CH, MgBr; then H,0 1.C, HMgBr (phenylmagnesium bromide), then H, O m. (CH). CHMgBr: then H.O a. Dess-Martin periodinane (DMP) Write the number/letters of the alchol reagents in the boxes below. Alcohol starting material Reagent for step! Reagent for step 2 Reagent for step 3 vicus )

Answer 1

dehydration O + ngar Target molecule Nucleophilic + addle god steg. I onidation - 1st stogo OH starting material calcohol, Cyelonerand. Porward synthesis 1st step: (g) -osidation and step. (K) -Nucleophilic addition Followed by and hydrodze onge medy crog 4150 step maffial) -dehydration (b) An first step cyclohexanol reats with crop in minhece of 48 (ho to generate cyclohexanona (onidized products, ar and step. proyl magnesion bromide affalls on carbony glapot cyclobenamone & Subjerred and hydrolyss to give coresponding 8- alcohol. an god step. - alohs was treated with Hot subsequently hay underwent dehydrafion to give / provide corresponding alsone a forget moleule.