Question

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b. How many products will be formed in the reaction below? (Do not show them) 1. NaOEVEIOH 2. Hyo What can you change, without altering the structures, to make only one product. selectively? Show the structure of that only product: 3. (10) Show in detail (e.g., order of addition) how you will synthesize the target and provide the full mechanism. (Hint: did you recognize the reaction?) some carbonyl compound+ needed reagents

Answer 1

The given starting materials:

H HH ethyl acetate ethyl butyrate

The given two starting material ethyl acetate has primary alpha acidic hydrogen but ethyl butyrate has secondary alpha acidic hydrogen. In the given reaction sodium ethoxide used as a base. Sodium ethoxide is not a bulky base so which will abstract the acidic hydrogen from both primary and secondary carbon. Sodium ethoxide will give two different product.

To get only one product without altering the structure

If we use bulky base it will abstract acidic hydrogen from less hindered centre (primary carbon). LDA is a strong and bulky base which will preferably abstract the acidic hydrogen from ethyl acetate. After formed enolate go and attack the ethyl butyrate and gives keto-ester as a product (only one keto-ester will form)

༧ ནང་། ད འཆདང་། '' ས net 1 OE+ ou radiolog e

For get only one product ; 'j- LDA - Lithium Disopropyl Amica LDA DE+ + -DET It DET Set Etor only one product

In this reaction, beta-aldehyde-ester is the target molecule. Nucleophilic attack on aldehyde gives the alcoholic product but we have synthesis the aldehyde compound. If aldehyde contains one leaving group means we can achieve the target molecule. Ethyl formate has ^-OEt as leaving group. While formed enolate attacks the Ethyl formate, ^-OEt will leave which will give the desired product.

soring PhoMe 1) NAOMe 2) HCOOH ere HT NO 1 1 1 - 1 ph Target Molecule + H et & Ngome Seclium me Ethylformate (carbonyl Compeerd) (Reagent