Orgo Road Map

[dds j]

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So I recently purchased the DAT destroyer book that contains 4 sections of orgo, gc, bio, and qr. Im trying to determine where this organic chem road map is in the book that everyone keeps talking about. Do I have the wrong book or should I be looking at a specific page number in this 2009 booklet.

Thanks in advance

 

[ZzZzSleepyhead]

Yo dds j,
Welcome to the forums 🙂. The roadmaps you seek are in the solutions for the organic chemistry section! There are several roadmaps in the solutions, just flip through quickly and you'll see em (they look like flowcharts). I would pull out the pages for you but I'm not at home. Off of the top of my head i recall the majority of the roadmaps are around solutions #130-ish.

 

[yumi43]

hi! the roadmaps are on pages 92-97 in the organic chemistry solutions section. there is also a small diazonium roadmap on page 106, so you should have 7 total roadmaps. these are golden. i made flashcards out of them and did well on the orgo portion of the real DAT. good luck!!

 

[una09]

for Road Map 2, middle left....
ethyl benzene reacting with potassium dichromate under acidic conditions shows the product as benzoic acid.... I thought it would have been 2-phenyl ethanoic acid ? Why do we lose one of the carbons ...

 

[suhshi]

for Road Map 2, middle left....
ethyl benzene reacting with potassium dichromate under acidic conditions shows the product as benzoic acid.... I thought it would have been 2-phenyl ethanoic acid ? Why do we lose one of the carbons ...

it oxidizes it no matter what chain length

 

[una09]

it oxidizes it no matter what chain length

ok so shouldn't it oxidize it to 2-phenyl ethanoic acid , not benzoic acid b/c when you oxidize it to benzoic acid, you are losing one carbon

 

[suhshi]

ok so shouldn't it oxidize it to 2-phenyl ethanoic acid , not benzoic acid b/c when you oxidize it to benzoic acid, you are losing one carbon

it will oxidize it all the way to a single carboxylic acid

 

[una09]

it will oxidize it all the way to a single carboxylic acid

okay so even if it was a propyl benzene, under these conditions, it would oxidize it to benzoic acid?

 

[suhshi]

okay so even if it was a propyl benzene, under these conditions, it would oxidize it to benzoic acid?

yup

 

[akeurogh]

Hey guys in the orgo road maps 4 and 5, the halogens being eliminated by E2 with tert butoxide are forming the least substituted alkene, why is this so? Shouldn't it follow the zaitsev rule?


thanks.

 

[una09]

Hey guys in the orgo road maps 4 and 5, the halogens being eliminated by E2 with tert butoxide are forming the least substituted alkene, why is this so? Shouldn't it follow the zaitsev rule?


thanks.

I think it's because t-butoxide is big so its a hindered base --> attacks the least hindererd carbon

 

[akeurogh]

that makes sense. thanks.

 

[americanpierg]

Yo dds j,
Welcome to the forums 🙂. The roadmaps you seek are in the solutions for the organic chemistry section! There are several roadmaps in the solutions, just flip through quickly and you'll see em (they look like flowcharts). I would pull out the pages for you but I'm not at home. Off of the top of my head i recall the majority of the roadmaps are around solutions #130-ish.

wow...ive had this book for 2 years and people kept saying roadmaps and i never knew what they were till now. haha

 

[americanpierg]

Hey guys in the orgo road maps 4 and 5, the halogens being eliminated by E2 with tert butoxide are forming the least substituted alkene, why is this so? Shouldn't it follow the zaitsev rule?


thanks.

large hindered bases = hoffman's rule