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Alcohol/aldehyde/ketone synthesis problems: Specify both the alcohol starting ma

ID: 489661 • Letter: A

Question

Alcohol/aldehyde/ketone synthesis problems:

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 CI Reagents Available Alcohol Starting Materials 1. methano a. LiAIH f. PBr3 k. 3CH2CH2MgB 2. ethanol b. H2SO4 g. Cro I, C6H5MgBr (phenylmagnesium bromide C. HCI 3. 1-propanol h, NaH m. (CH3)2CHMgBr 4. 2-propanol d. HBr i. CH3MgBr n. pyridinium chlorochromate (PCC) 5, cyclohexanol e, SOC j. CH3CH2MgBr Write the number/letters of the alchol/reagents in the boxes below Alcohol starting material 3 Reagent for step 1 g Reagent for step 2 Reagent for step 3

Explanation / Answer

A

Alcohol starting material is 2 i.e., ethanol

Reagent for step 1 is g. (CrO3 will convert alcohol to aldehyde)

Reagent for step 2 is m. [(CH3)2CHMgBr will react with aldehyde to give an alcohol]

Reagent for step 3 is e. (SOCl2 by SN2 reaction will give the desired compound)

B

Alcohol starting material is 2 i.e., ethanol

Reagent for step 1 is g. (CrO3 will convert alcohol to aldehyde)

Reagent for step 2 is k. [(CH3CH2CH2MgBr will react with aldehyde to give an alcohol]

Reagent for step 3 is f. (reaction with PBr3 will give the desired compound)

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