Specify both the alcohol starting material and the reagents you would use in eac

Question

Specify both the alcohol starting material and the reagents you would use in each step in a synthesis of the compound shown

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 steps enter "none" for step 3 CH3 CH2 Alcohol Starting Materials 1. methanol 2. ethanol 3. 1-propanol 4. 2-propanol 5. cyclohexanol Reagents availablie a. LiAlH4 f. PBr3 k. CH3 CH2CH2; then H3O b. HS0. CrOs, H,S0, H2OCHMgBr (phenylmagnesium bromide); then Hso m. CH3)2CHMgBr: then HO d. HBr i. CHsMgBr then H30+ n. Dess-Martin periodinane (DMP) then H,o.Dess-Martin

Explanation / Answer

Alcohol starting material is: 4) 2-propanol

step:1: n) Dess-Martin periodinane (DMP)

step:2: l) C6H5MgBr (pehnyl Magnesium bromide) then H3O+

step:3: b) H2SO4

Explanation: oxidation of 2-propanol produces ketone as product. reaction of ketone with phenyl magnesium bromide produces tertiary alcohol as product. dehydration of alcohol with H2SO4 produces the required alkene as product.

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