PRACTICE Exam 3 Su 15 X 6 Part D: Provide the major product(s) for the following

Question

PRACTICE Exam 3 Su 15 X 6 Part D: Provide the major product(s) for the following reactions ctions (36 poir (86 points) 6 1) 2 moles CoHs Li i) excess Bry ii) NaOH 2) H+ workup 2) H+ workup 4 pts 4 pts 1) NaCN COOH 2) H3O COOH 6 pts OH 1. SOCl2 OCH2CH3 2. CH3CH2OH 3) 6 points OH I equivalent i) HO ii) C,H ii) C2H5MgBr excess 4) iii) H3O alipahtic aldehydes are more reactive than aromatic aldehydes, react with diol and 4 pts alipahtic aldehydes are more reactive than aromatic aldehydes, react with diol and form 4 pts OH H2SO4, H20 CgH5 Diethyl ether heat 2) Ho 4 pts

Explanation / Answer

1) first condition one mole of the reagent will get quenched by the H+ of the acetic acid and second mole will react with carbonyl followed by acid work up and gave the methyl aryl ketone

second condition is haloform reaction followed by acid work up by product is CHBr3

2) nucleophilic addition of the NaCN to carbonyl followed by hydrolysis first option is the answer

3) socl2 will convert the acid to acid chloride followed by ethy alcohol attack gives the ester

4) out of two,aldehydic groups aro matic saldehyde is less reactive and aliphatic is more reactive so that will het protect and the remaining will under go grinard reaction will give you the product

5) H2SO4 is the strong acid it can allow the hydrolysis of CN group and it can do the cleavage of Acetol protecting group also

CN group also under go addition of grignard reagent same like carbonyl but here only one equilent followed by acid hydrolysis give you the product.

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