Drawing arrows

We last discussed mechanisms in Chapter 5 where we introduced basic arrow-drawing. A lot has happened since then and this is a good opportunity to pull some strands together. You may like to be reminded ... 

FIGURE 10.6 Electron micrograph of an n-butylammonium vermiculite gel prepared in a 0.01 M n-butylammonium chloride solution. The scale is defined by the white bar, which represents 200 nm. The method of determining the interlayer spacing is indicated by the line drawn perpendicular to the vermiculite layers. The large arrow points out one example of a bifurcation, and the two smaller arrows draw attention to two neighboring bifurcations that affect the estimation of the layer spacing. 

To develop your arrow-drawing skill in a more difficult example. 

With a pencil, now mark off on the shaft the places where the feathers are to go. One inch and a quarter from the end of the arrow draw a circular line. This is for the rear binding. Four and three quarters inches from this draw a similar line which marks the beginning of the front binding. At right angles to the nock draw a perpendicular line which indicates the position of the cock feather. Two similar lines are drawn equidistant from this, for the other feathers. When all ate set they will appear as in Fig 89. 

Drawing the resonance stmcture of the following compound requires one curved arrow. The head of this curved arrow is placed on the oxygen atom, and the tail of the curved arrow can only be placed in one location without violating the rules for drawing curved arrows. Draw this curved arrow. 

Using one curved arrow, draw the carbocation rearrangement. 

STEP 2 Using one curved arrow, draw a carbocation rearrangement that forms a more stable carbocation, via either a hydride shift or a methyl shift. 

Every step has two curved arrows. Draw them precisely. 

Following the curved arrows, draw a resonance structure for the HCONH ion. 

Thalidomide is converted to the drug CC-4047 by substitution of an amino group for one of the H atoms on the aromatic portion of the molecule. Using curved arrows, draw the mechanism for this reaction and all the resonance structures for the carbocation intermediate. [144 Sample Problem 10.7]... 

By following the curved red arrows, draw the product(s) of each of the following reaction steps ... 

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