6. Answer ALL parts. (a) For the scheme shown below, give...

6. Answer ALL parts. (a) For the scheme shown below, give structures for compounds A to H. showing stereochemistry where applicable. (b) Assign specific bond vibrations to the infrared spectral data provided. (c) Provide a mechanism for the conversion of D into E. conc. H$_2$SO$_4$ B C$_7$H$_{14}$O MeMgI then aq. NH$_4$CI A C$_6$H$_{10}$O O$_3$ then Me$_2$S F C$_7$H$_{12}$O$_2$ Conc. NaOH THF\-BH$_3$ then NaOH, H$_2$O$_2$ C C$_7$H$_{14}$O CI CrO$_3$ D C$_7$H$_{12}$O [16] [2] [2] CO$_3$H (m-CPBA) H C$_7$H$_{12}$O $\nu_{max}$ = 1725 cm$^{-1}$ H$_2$, Pd-C G C$_7$H$_{10}$O $\nu_{max}$ = 1695 and 1640 cm$^{-1}$ E C$_7$H$_{12}$O$_2$ $\nu_{max}$ = 1740 cm$^{-1}$

Transcript

00:01 In this problem, you're given a molecular formula, a proton in a mar, and then some key features from ir.

00:08 So to start with, let's bind degrees of unsaturation.

00:13 So that will tell us how many double bonds or rings we have.

00:17 So to do that, we do two times the number of carbons plus two, minus the number of hydrogens, minus the number of halogens, so that's for the chlorine, over two.

00:31 And for this we have five.

00:33 Now, the more problems you do like this, you'll start to recognize, usually when you see five as degrees of insaturation, you're going to end up having a benzene ring.

00:44 So that gives you four degrees of insuration because you have three double bonds and you have a ring.

00:50 So that's four.

00:53 And now that tells us we still have one more double bond or ring.

00:57 And the inflammation for that can be found down here with our ir.

01:02 So this stretch at 1685, that's usually indicative of a carbonyl.

01:12 And the broad hydroxy peak there, that usually means we have a carboxylic acid.

01:22 So we add these two together that gives us five degrees of unsaturation.

01:27 So we know we have a ring, we have carboxylic acid.

01:37 And if we look at our proton nmr, we have five hydrogens.

01:44 So when we're looking at this, this can tell us that maybe, even though often this together means we have a carboxylic acid, this is a very low peak for that.

02:08 So if we did have a carboxylic acid, we'd be looking from like 10 to 12 parts per million...

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