--KEY--Chemistry 108B Exam #1-Winter 2015--KEY--
9 = 2@ expl; 1 @ drawing You've just opened your new custom chemicals company, company, Ketones 'R' Us. In an effort to put Aldrich out of business, you will synthesize only ketones Aldrich does not stock. You You carry out the reactions shown below. bel ow. However, However, all of your claiming there were no ketones in ketones in customers who purchased Ketones A-C returned their products with nasty notes claiming there products for all three reactions and use those drawings to specifically any of the bottles. DRAW the EXPECTED products for explain whether or not your customers were justified in being so upset.
PLEASE NOTE THE FOLLOWING: the word DRAW requires DRAW requires the application of an implement capable of marking paper with a pictorial representation of representation of ideas. Many of you do NOT seem to know the definition of this very important word and should consult your dictionary immediately...
DRAWING
O
OH
Jones' Reagent
A
DRAWING O
OH
B
Jones' Reagent
DRAWING OH Jones'
C
Reagent
Uh, Gary, isn't that FIVE BONDS TO CARBON??!!?? Like, whoa, dudes and dudettes: I am surrounded by genius!! NO OXIDATION can OXIDATION can occur on a 3° C-OH and therefore no ketone will ketone will be formed, so your customers had a right to be upset: you sent them a mixture of starting material and acid-catalyzed dehydration products! trend being set in this Maybe I'm overreacting here, but do I see a trend being problem? FIVE BONDS to Carbon AGAIN??!!?? OXIDATION can occur on an aromatic C-OH because, as in A, NO OXIDATION can an impossible compound would be formed, so, once again, your customers had a right to be upset: you sent them pure starting material. Seems more like you're competing with Heza Dodo to me... trend! We are now at the opposite end Ha! So much much for that trend! ROH will be of the oxidative spectrum: over-oxidation! A 1° ROH will O oxidized exclusively to the corresponding carboxylic acidby acidby the Jones' Reagent, so no ketone will form here. Besides, OH even if the oxidation stopped at the carbonyl, carbonyl, you'd still have an aldehyde, aldehyde, not a ketone, ketone, so don't quit your day job just yet...
Fill in the missing reagents above the arrows to complete each step in the synthesis shown below. bel ow.
1 @ correct reagent
McMurry 16.72
O Cl
O
, AlCl3
H2, Pt/C
0 for no AlCl3 catalyst
Br
KOH (E2) Br
-1 for no Br2, sep o,p ; FeBr3 (sep o,p ) 0 for no FeBr3 catalyst NBS
Br
(Benzylic bromination) bromination)
Br
