9. For the following reaction step, indicate which pattern...

9. For the following reaction step, indicate which pattern of arrow pushing it represents. A. Proton transfer B. Loss of leaving group C. Nucleophilic attack D. Rearrangement 10. For the following reaction step, indicate which pattern of arrow pushing it represents. A. Acid/Base proton transfer B. Loss of leaving group C. Nucleophilic attack D. Carbocation rearrangement Extra point question - 10 points 11. The following reaction has three mechanistic steps. Draw all curved arrows necessary complete the mechanism starting at top left and moving counterclockwise.

Transcript

00:01 All right, so for number nine here, we have this methanol is attacking the ketone, and it's creating this alcohol group and adding in this methyl group.

00:22 So from the arrow pushing, if we look at what's going on, we don't have a proton transfer because protons are still attached to what they were before.

00:33 We don't have a loss of a leaving movement.

00:35 Nothing's leaving the original structure.

00:37 We might have a nucleophilic attack because something that has a high electron density is attacking something with low electron density.

00:46 So it's attacking the nucleophile, or the nucleophile is attacking that electrophilic center underneath the carbonyl, and we don't have anything rearranging itself.

00:58 So number nine is an example of nucleophilic attack.

01:03 For the next one, we have a positive, charge on a secondary, we have a secondary carbocation, but then after this arrow pushing, we have a tertiary carbotagon.

01:17 So nothing has been added to the structure.

01:19 The arrow is blank.

01:20 And so the only thing that's going on is this proton is moving.

01:24 So is this acid -based proton transfer? well, we do have a proton moving, but we don't see an acid or base that's participating in this particular step.

01:33 So it's probably not going to be acid -based proton transfer.

01:36 We don't have a loss of a leaving group because everything on the atom is still there, it's just moving within the atom.

01:43 We don't have nucleophilic attack because something is not attacking this structure...

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