Organic Chem Midterm 1 multi+key
1
You've just opened your new custom chemicals company, Ketones 'R' Us. In an effort to put Aldrich out of business, you will synthesize only ketones Aldrich does not stock. You carry out the reactions shown below. However, all of your customers who purchased Ketones A -C returned their products with nasty notes claiming there were no ketones in any of the bottles. DRAW the EXPECTED products for all three reactions and use those drawings to specifically explain whether or not your customers were justified in being so upset. OH OH Jones' Reagent Jones' Reagent OH Jones' Reagent O Uh, Gary, isn't that FIVE BONDS TO CARBON??!!?? Like, whoa, dudes and dudettes: I am surrounded by genius!! NO OXIDATION can occur on a 3° C-OH and therefore no 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! O Maybe I'm overreacting here, but do I see a trend being set in this problem? FIVE BONDS to Carbon AGAIN??!!?? NO OXIDATION can occur on an aromatic C-OH because, as in A , 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... --KEY--Chemistry 108B Exam #1-Winter 2015--KEY-- Ha! So much for that trend! We are now at the opposite end of the oxidative spectrum: over-oxidation! A 1° ROH will be oxidized exclusively to the corresponding carboxylic acidby the Jones' Reagent, so no ketone will form here. Besides, even if the oxidation stopped at the carbonyl, you'd still have an aldehyde, not a ketone, so don't quit your day job just yet... OH O PLEASE NOTE THE FOLLOWING: the word DRAW requires the application of an implement capable of marking paper with a pictorial 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 DRAWING DRAWING B C A Fill in the missing reagents above the arrows to complete each step in the synthesis shown below. O Br Br Br Br McMurry 16.72 Cl O , AlCl 3 H 2 , Pt/C Br 2 , FeBr 3 (sep o,p) NBS KOH (E2) (Benzylic bromination) -1 for no sep o,p; 0 for no FeBr 3 catalyst 0 for no AlCl 3 catalyst 9 = 2@ expl; 1 @ drawing 1 @ correct reagent
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Transcript of Organic Chem Midterm 1 multi+key
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You've just opened your new custom chemicals company, Ketones 'R' Us. In an effort to put Aldrich out of business, you will synthesize only ketones Aldrich does not stock. You carry out the reactions shown below. However, all of your customers who purchased Ketones A-C returned their products with nasty notes claiming there were no ketones in any of the bottles. DRAW the EXPECTED products for all three reactions and use those drawings to specifically explain whether or not your customers were justified in being so upset.
OH
OH
Jones'Reagent
Jones'Reagent
OH Jones'Reagent
O
Uh, Gary, isn't that FIVE BONDS TO CARBON??!!?? Like, whoa, dudes and dudettes: I am surrounded by genius!! NO OXIDATION can occur on a 3 C-OH and therefore no 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!
O
Maybe I'm overreacting here, but do I see a trend being set in this problem? FIVE BONDS to Carbon AGAIN??!!??NO OXIDATION can occur on an aromatic C-OH because, as in A, 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...
--KEY--Chemistry 108B Exam #1-Winter 2015--KEY--
Ha! So much for that trend! We are now at the opposite end of the oxidative spectrum: over-oxidation! A 1 ROH will be oxidized exclusively to the corresponding carboxylic acidby the Jones' Reagent, so no ketone will form here. Besides, even if the oxidation stopped at the carbonyl, you'd still have an aldehyde, not a ketone, so don't quit your day job just yet...
OH
O
PLEASE NOTE THE FOLLOWING: the word DRAW requires the application of an implement capable of marking paper with a pictorial 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
DRAWING
DRAWING
B
C
A
Fill in the missing reagents above the arrows to complete each step in the synthesis shown below.
O
BrBr
Br
Br
McMurry 16.72
Cl
O
, AlCl3 H2, Pt/C
Br2, FeBr3
(sep o,p)
NBSKOH (E2)(Benzylic bromination)
-1 for nosep o,p;0 for no
FeBr3 catalyst
0 for noAlCl3 catalyst
9 = 2@ expl; 1 @ drawing
1 @ correct reagent
