A. TLC question. Diol A reacted with 1 equivalent of the...

A. TLC question. Diol A reacted with 1 equivalent of the Chal (nucleophilic substitution) with a formation of the mixture of B and C. On the right you see the TLC of the reaction mixture when all 3 compounds are present. HO A KOH, CH3I OH KOH, CH3I HO B R_f = 0.58 R_f = 0.33 R_f = 0.15 C Based on polarity of A, B and C, match each molecule with its spot on the TLC plate (fill in 3 boxes with letters, one box-one letter of the molecule). B. Distillation question. Alcohol D oxidized to aldehyde E and then to carboxylic acid F according to the following scheme. Based on the structures of all 3 molecules, match the boiling points with a structure of the molecules (fill in 3 boxes with letters, one box-one letter of the molecule). Higher OH CrO3 CrO3 OH hyhu D E b.p. = 131 °C b.p. = 92 °C b.p. = 176 °C F C. Extraction question. Reaction mixture (with all 3 molecules) from part B was extracted with CH2Cl2-water system (see separatory funnel on the right). Predict the content of Organic Layer: Aqueous layer: H2O + ? CH2Cl2 + ?

Transcript

00:01 Okay, so we're asked to answer the following questions, and we are starting with this structure.

00:12 So you have an ester, an oxygen bounce, an ethyl, and we want to create ethanol.

00:20 So if we react this with lithium -molubleodum hydride over h3 plus, it's going to reduce the ketone into an alcohol and get rid of the ester.

00:31 So reduction is the addition of hydrogens.

00:35 So on the left, we have three, and on the right, we have two.

00:40 Three, six, so it's reduction.

00:52 So for b, we have to give the structure of compound three, reacting with two phenol magnesium bromides.

01:08 So phenol magnesium bromide, magnesium bromide makes it a greener artery agent, and the carbon is going to attack the ketone, converting the alcohol into, or converted the ketone into an alkalion.

01:25 So we're going to get this structure.

01:32 But then instead of expelling the phenol or the methyl, it's going to regenerate this bond and expel the ester.

01:42 So we'll get the ketone back, and they're reacting this with phenyl magnesium bermine again.

01:47 It's going to attack the ketone again.

01:50 And this time we'll get an alcohol.

01:53 So we'll eventually get, so without showing the mechanism.

02:04 So again, this carbon is nucleophilic.

02:06 It's going to attack the carbonyl carbon, and we'll eventually get this intermediate.

02:12 It.

02:14 So instead of expelling either a phenol or a methyl, it's going to depurtenate an acid, and we'll get an alcohol with two phenols.

02:37 So we got rid of the ester.

02:40 Then for for ci, we have to show the mechanism for how one is converted into four.

02:54 So if we react the structure with acid, the ketone is going to interact with the acid.

03:02 It's going to depotinate it.

03:07 So now it's a positive charge because it donated a pair of electrons or a negative.

03:14 The next step is for a water molecule.

03:18 So i'm going to use a different color because this is the question for d -a -2.

03:25 This is oxygen 18.

03:28 And it's going to attack the carbonyl carbon, to create a ketone into an alcohol.

03:39 You have the addition of an oh2.

03:49 This should be the positive charge.

03:57 And we still have the estuarine here.

04:01 So another water molecule.

04:04 Is going to deprotinate.

04:09 We're going to get the structure to oh.

04:22 So at this point, the ester is going to interact with water to turn itself into a better leaving group.

04:57 So because we have a better leaving group, the bond between the oxygen and this carbon is going to reform, giving us a ketone and expelling this group...

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