Question

Indicate appropriate conditions and reagents for effecting the following transformations. Identify necessary co-reactants, reagents, and catalysts. One-pot processes are possible in all cases. Figure can't copy

    Indicate appropriate conditions and reagents for effecting the following transformations. Identify necessary co-reactants, reagents, and catalysts. One-pot
processes are possible in all cases.
Figure can't copy
Advanced Organic Chemistry, Part B: Reaction and Synthesis
Advanced Organic Chemistry, Part B: Reaction and Synthesis
Francis A. Carey,… 5th Edition
Chapter 8, Problem 4 ↓
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Indicate appropriate conditions and reagents for effecting the following transformations. Identify necessary co-reactants, reagents, and catalysts. One-pot processes are possible in all cases. Figure can't copy
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00:04 Suppose we're given a reagent, such as this aromatic alcohol, and we want to produce this ester.
00:25 How would we go about doing that? well, for starters, we need to make a carboxylic acid derivative from an alcohol.
00:37 So we need to make a carboxylic acid before we can do so.
00:41 So for the first step, what we can do is oxidize that alcohol.
00:52 And what can we use to oxidize a primary alcohol, so primary alcohol, into a carboxylic acid? we can use jones reagent, or we can specify it as h2cro7 chromic acid, or h2cr .o4 chromis acid.
01:20 And what we can and what that would do is well oxidize that primary alcohol into a carboxylic acid and now to go from a carbaclylic acid to an ester we would need to use an alcohol and catalytic acid so our acid could be really anything as long as we have it in catalytic amounts let's use h2s .o4 in catalytic amounts and what what would our alcohol be? well, we're adding a ch3, so we want to make ch3, or we want to use ch3 -o -h, methanol.
02:10 And that would be how we would conduct this synthesis.
02:16 Let's try another example.
02:19 How about if we were given this ester, and we wanted to produce this carboxylic acid with an alcohol group? well, this just looks like a hydrolysis of an ester to a carboxylic acid, which would create another alcohol, but since it's connected from the other side of the chain, it would just be ring opening.
02:51 So what we can do is h2o with catalytic h2s .4.
03:09 What about this example? how do we take this nitral group and produce this alkalide, or alkalinoil halide? or acyl halide, however you want to call it.
03:29 There's multiple names for it.
03:34 Well, we can't go directly into the acyl halide.
03:41 And the reason is you cannot go from a weak carboxylic acid derivative to a strong.
03:55 You cannot go weak to strong.
03:56 You can only go strong to weak.
03:59 But what we can do is hydrolyze this nitral group, h2o, with calcium.
04:08 Catalytic h2s -o -4, really any acid and catalytic amounts would do just fine.
04:19 And we would apply heat, and this would make a carboxylic acid.
04:29 And then, well, we can either use pcl -5 or so -cl -2 to make our alcono -halide from our carboxylic acid.
04:46 What if we had this acyl halide or alconol chloride and we wanted to make an aldehyde? what would we use there? well, we want a really strong reducing agent, but alconol halides are very reactive, so we cannot really use lithium aluminum hydride...
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