18. Which one of the following compounds would react with...

18. Which one of the following compounds would react with C2H5MgBr to make 3-pentanol? A) ethanal B) ethyl formate C) acetic acid D) acetone 19. Which sequence would accomplish the following? Assume acid workup. O= -CO2Me -> O= -C(CH3)(CH3)OH A) 2 CH3MgBr B) 1) HOCH2CH2OH/H+, 2) LiAlH4, 3) 2 CH3MgBr C) 1) HOCH2CH2OH/H+, 2) 2 CH3MgBr D) 1) HOCH2CH2OH/H+, 2) DIBAIH, 3) 2 CH3MgBr E) 1) NaBH4, 2) TsCl, 3) 2 CH3OH/OH-

Transcript

00:01 Hi, in this question we are given with two parts.

00:03 In the first part of the question we are asked to select the correct compound that react with c2h5 mgbr which is a grignard reagent to form 3 -pentanol.

00:14 In 3 -pentanol we can say that we will be having 5 carbon atoms and there is oh group attached on the third carbon atom.

00:25 We can say that we need 3 carbon atoms since we are having 2 carbon atoms from grignard reagent and we need 3 carbon atoms in the compound.

00:36 Therefore, we can take ethyl formate.

00:39 We can draw the structure of ethyl formate here in this manner.

00:45 This is ethyl formate and in grignard reagent we are given c2h5 mgbr.

00:54 Carbon is electronegative here, therefore we will put delta negative here and magnesium is electropositive, therefore we will put delta positive here.

01:04 There is electronegativity difference between carbon and oxygen, therefore this bond will move towards oxygen and this carbon will become electron deficient.

01:14 As a result, this nucleophilic carbon will attack at this carbon and we will be getting this structure.

01:21 Here we have negative charge, therefore we can write here mgbr in this manner.

01:30 Now in the next step there will be hydrolysis in presence of h3o positive, we will be getting 3 -pentanol.

01:40 We can draw this 3 -pentanol in this manner also.

01:46 Hence, we can say that we are getting this 3 -pentanol from the compound named ethyl formate which is given in option b and the structure of ethyl formate is this.

02:02 This is the answer of first part.

02:04 Now let us take a look on the second part.

02:07 In the second part, we need to select the correct reagent for this transformation...

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