BrCH2CH2COCH3-> PhCH2CHOHCH2CH2COCH3

[cun]

BrCH2CH2COCH3--> PhCH2CHOHCH2CH2COCH3

Homework Statement

synthesis ...4 step

Homework Equations

BrCH2CH2COCH3--> PhCH2CHOHCH2CH2COCH3

The Attempt at a Solution

SOLVE THE REATION IN 4 STEP

 

[cun]

i think the first step it may be SN2 reaction to release Br...

 

[Blueshift5]

Step 1: First, the bromine atom (Br) in BrCH2CH2COCH3 needs to be replaced with a phenyl group (Ph) to form PhCH2CH2COCH3. This can be achieved by reacting BrCH2CH2COCH3 with a phenylmagnesium bromide (PhMgBr) in an ether solvent, such as diethyl ether. This will result in the formation of a Grignard reagent, which will react with the carbonyl group in BrCH2CH2COCH3 to form PhCH2CH2COCH2MgBr.

Step 2: Next, the magnesium bromide (MgBr) group needs to be replaced with a hydroxyl group (OH) to form PhCH2CH2COCH2OH. This can be achieved by treating PhCH2CH2COCH2MgBr with water (H2O) and a proton source, such as hydrochloric acid (HCl). This will result in the formation of an alcohol, PhCH2CH2COCH2OH.

Step 3: In order to form PhCH2CHOHCH2CH2COCH3, the carbonyl group needs to be reduced to a hydroxyl group. This can be achieved by using a reducing agent, such as sodium borohydride (NaBH4) or lithium aluminum hydride (LiAlH4), in a solvent, such as tetrahydrofuran (THF). This will result in the formation of PhCH2CHOHCH2CH2COH.

Step 4: Finally, the carboxylic acid group (COOH) needs to be converted to an ester group (COOR) to form PhCH2CHOHCH2CH2COCH3. This can be achieved by reacting PhCH2CHOHCH2CH2COH with an acid chloride, such as acetyl chloride (CH3COCl), in the presence of a base, such as pyridine (C5H5N). This will result in the formation of the desired compound, PhCH2CHOHCH2CH2COCH3.

Overall, the synthesis of PhCH2CHOHCH2CH2COCH3 from BrCH2CH2COCH3 involves four steps: 1) replacing the bromine atom with a phenyl