So im trying to make 1-acetylcyclohexane from ethenylcyclohexane..and i have to make it in 4 stepsi got the first two steps but the last two is what i am unsure of..
1) Br2
2) 2 equiv NaNH2
3) ??
4) ??
i know the 1st two steps but im having trouble figuring out the last two steps here is the bank:
*excess NaNH2, then H2O
*bromocyclohexane
*NaBH4
*BH3/THF
*CH3Br
*SOCl2
*HBr
*H2
*H2, Lidlar catalyst
*CH3CH2Br
*H2O,H2SO4, HgSO4
*H2O2, NaOH, H2O
I originally thought it would be
1)Br2
2) 2 equiv NaNH2
3) H2O, H2So4, HgSO4
4) BH3/THF
....but that's wrong, can you please help me? Thank you!! :)
To convert ethenylcyclohexane to 1-acetylcyclohexane using the given reagents, you need to choose the appropriate steps from the provided bank. Let's go through the steps one by one:
1) Br2: This step is already given, and it will add a bromine atom (Br) across the double bond of ethenylcyclohexane, forming bromocyclohexane.
2) 2 equiv NaNH2: This step involves the use of excess sodium amide (NaNH2) as a strong base. It will deprotonate the acidic hydrogen atom of bromocyclohexane, leading to the formation of a carbanion.
Now, let's look at the remaining options in the bank:
*excess NaNH2, then H2O: This step involves the addition of excess sodium amide followed by water. It is commonly used to convert a carbanion intermediate to an alcohol functional group. This option is not suitable for the desired synthesis of 1-acetylcyclohexane.
*NaBH4: Sodium borohydride (NaBH4) is usually used as a reducing agent to convert carbonyl groups (such as ketones) to alcohols. This option is also not applicable here.
*BH3/THF: Borane (BH3) in tetrahydrofuran (THF) is a reagent commonly used for hydroboration-oxidation reactions. It adds a boron atom to the double bond regioselectively (anti-Markovnikov), forming an organoborane intermediate. This option is not suitable for the desired synthesis of 1-acetylcyclohexane.
*CH3Br: Methyl bromide (CH3Br) is an alkylating agent used to convert nucleophiles to alkylated products. This option is not related to the desired synthesis.
*SOCl2: Thionyl chloride (SOCl2) is commonly used to convert alcohols to alkyl chlorides. This option is not relevant in this case.
*HBr: Hydrobromic acid (HBr) can be used to add a bromine atom across a double bond, but it is not the best option for the desired synthesis.
*H2: Hydrogen gas (H2) is used in hydrogenation reactions to reduce double bonds to single bonds. This option is not suitable for the desired synthesis.
*H2, Lidal catalyst: Lidlar catalyst is a selective catalyst used for the reduction of alkenes to alkanes without reducing other functional groups. This option is not applicable to the desired synthesis.
*H2O2, NaOH, H2O: This step involves the use of hydrogen peroxide (H2O2) in the presence of sodium hydroxide (NaOH) as an oxidizing agent. It is commonly used in the Baeyer-Villiger oxidation reaction to convert ketones into esters. This option is also not applicable here.
Based on the available options, it seems that none of them directly fulfill the last two steps required for the synthesis of 1-acetylcyclohexane. It is possible that the correct reagents for those steps are not provided in the given bank, or the synthesis may require different reagents altogether.
To proceed further and complete the synthesis, you may need to consult additional resources or literature to find the appropriate reagents and conditions for the desired transformation.