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How would you synthesize the following substances from benzaldehyde and reagents

ID: 1029301 • Letter: H

Question

How would you synthesize the following substances from benzaldehyde and reagents from the table? In general, the fewer the steps, the better the synthesis. You should not need more than four steps.
Use letters from the table to list reagents in the order used (first at the left) with no commas.
Example: cag

CH2-o f 1. CH3MgBrI dry ether j 1. P(C6H5)3 2 H30 in CH2Cl2 2. H30 2. H202 NaOH 2. BuLi 9Dess-Martin periodinane Br2 h . NaBH4 PBr3 NaNH2/ NH3 Mg/ dry ether (C6H5)3P-CH2 NHacid i 1. BH3/ THF m e CrO3/ H3O n a) b)

Explanation / Answer

Reagents for synthesis of compound A: fgd

Explanation: Reaction of grignard reagent with aldehyde produces alcohol as product. oxidation of alcohol with dessmartin-periodinane produces ketone as product. Reaction of ketone with secondary amine produces enamine as product.

Reagents for synthesis of compound B: ckm

Explanation: Reaction of aldehyde with phosphonium ylide produces alkene as product. Addition of Br2 to alkene produces dibromo compound as product. NaNH2 is a strong base which gives elimination reaction and produces alkyne as product.

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