The Following are WTF Reactions:

[2PacClone23]

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1)

Why is this no reaction? Wouldn't the C=O bond turn into C-OH?

2)

Woah, what is attacking what? I thought "I" would be attacking the carbonyl but I guess not.

3)

No freakin' clue here

4)

I thought OH was a crappy leaving group. Is the H protonating it to make water (good leaving group) and then attacking with the I?

5)

Isn't this Wolf-Kishner/Clemenson reduction? I don't get why HCl gets removed, let alone twice.

6)

NH3 attacks and I thought it would just be a primary amine. Why the double bond?

7)

This one's just ridiculous. WTF is going on?

8)

Another WTF reaction that I have no idea about. Why would everything be reduced to a benzylic amine?

9)

Why would H3O+ turn a nitrile into a COOH group?

10)

Looks like #6. Still no idea.


*MORE PICTURES ON THE NEXT POST*

 

[2PacClone23]

11)

I didn't know K2Cr2O7 was that strong of an oxidizing agent to turn alkane substituents into COOH groups. Doesn't KMnO4 do the same thing?

12)

Looks like #6 and #10. Still no clue.

13)

Since when does D and H3O+ cause water elimination and formation of the alkene?

 

[invictusx]

1. Because you can't reduce an ester
2. Methyl Iodoform test, it checks if there is a methyl group on the carbonyl
3. Look at polarity
4. SN1
5. Not wolff-kischner/clemenson. It's just a double elimination..
6. Readily accessible H that could be deprotonated to eliminate the positive charge.
7. No idea
8. Hoffman Rearrangement with secondary amines
9. -CN can be protonated to HCN and becomes a good LG.
10. acyl halide + primary amine = amide
aldehyde/ketone + primary amine = imine
aldehyde/ketone + secondary amine = enamine
11. K2Cr2O7 is a very strong oxidizing agent as well as KMnO4
12. Look at 10
13. Simple elimination

 

[lmaozedong1]

Wtf!!!

 

[FROGGBUSTER]

1. NABH4 only reduces aldehydes and ketones, you would need LAH to reduce this ester.

2. You're asking about the mechanism, but that's not necessary for the DAT. Just know what happens when methyl ketones react with a halogen (X2) & OH-.

3. Same thing as #2, memorize this reaction. If you want the mechanism, google "Haloform reaction mechanism."

4. Yes that is what happens.

5. This is not WK/Clemenson, this is a double elimination reaction in which NaNH2 acts as a base. Vicinal dihalides + excess strong base --> alkyne.

6. The reason is because condensation occurs. Ketone/aldehyde + Primary amine --> Imine. You don't have to know the mechanism but actually it probably would help you remember the reaction in this case.

7. Just memorize it.

8. Amide + X2, OH- --> Amine (minus 1C). Just memorize this.

9. Just memorize it. Nitrile + acidic water --> Carboxylic acid.

10. Same as #6.


A lot of these you can just memorize without knowing the mechanism. If you think knowing the mechanism will help you though, Google is your friend. Almost all of your questions were about the mechanisms, and that's tough to explain over the Internet, so look in your textbook or online.

 

[FROGGBUSTER]

Also, I suspect you're leaping into the problem sets without having had reviewed the material yet. That's not a good idea and it will get you discouraged and confused. Do you have access to Chad's? If not, buy a subscription --> watch the vids and take notes if necessary --> THEN do the problem sets.

 

[2PacClone23]

Thanks to both of you guys! Really cleared up some things and what things I really need to memorize.


I'm making flash cards of all the roadmaps so it's been exhausting. I've already gone through all of Destroyer once. Another 2-3 times and I shall be good.


I also plan on watching Chad's videos at 2x speed (GChem + OChem).

My test is on the 9th.

 

[loganheinrich]

My test is also on the 9th, and I pretty much had the exact same response to the exact same questions that you had on the roadmaps. Instead of making flash cards, I found that it was most helpful just to copy each one until I had it memorized. It only took about 5 copies apiece to get it memorized and I've been copying each one about twice a week since then to reinforce everything. Anyway, i definitely found that copying the roadmaps was helpful. Also, you'll find that iodoform test on the page after the baby roadmaps, where he talks about the lab tests.

 

[loganheinrich]

Also, I've been going through Chad's this week for the third time. The first two times I took my own notes, this time I have his guide and it's pretty great, in fact, it's basically all of the roadmaps in a form that explains which category the reaction is in and with some other good explanation. I recommend printing out his guide when you go through the vids.

 

[2PacClone23]

Also, I've been going through Chad's this week for the third time. The first two times I took my own notes, this time I have his guide and it's pretty great, in fact, it's basically all of the roadmaps in a form that explains which category the reaction is in and with some other good explanation. I recommend printing out his guide when you go through the vids.

I don't take notes for Chad's. I'm a great listener.

I take the quizzes though. Regardless, I have his old videos downloaded so I can go at them with like 3x speed as opposed to the newer 2011 videos.

I've only gotten through them once. 2x Chad + 2x Destroyer + Topscore 1-3 + 3CDP's + 3 CDM's = what I have left to do.

 

[knugget]

there's a huge difference between passive studying and active studying. and the knowledge you know about the reactions above reflects that difference.

 

[invictusx]

there's a huge difference between passive studying and active studying. and the knowledge you know about the reactions above reflects that difference.

👍

 

[2PacClone23]

there's a huge difference between passive studying and active studying. and the knowledge you know about the reactions above reflects that difference.

I've done both 🙂

 

[free99]

This thread is actually pretty solid. Many of the reactions this guy highlighted had me stumped, too. Hope this helps someone else out who's gearing up for the big day!

 

[Msmouth]

Thanks to both of you guys! Really cleared up some things and what things I really need to memorize.


I'm making flash cards of all the roadmaps so it's been exhausting. I've already gone through all of Destroyer once. Another 2-3 times and I shall be good.


I also plan on watching Chad's videos at 2x speed (GChem + OChem).

My test is on the 9th.

Wow flashcards? If you're not knee deep into flash cards try copying road maps either by hand without the answers or copy the page and then white out answers....then copy page a few times for your own personal work sheets. I personally think seeing the entire road map is more helpful than trying to see the reactions individually.

 

[Msmouth]

I don't take notes for Chad's. I'm a great listener.

I take the quizzes though. Regardless, I have his old videos downloaded so I can go at them with like 3x speed as opposed to the newer 2011 videos.

I've only gotten through them once. 2x Chad + 2x Destroyer + Topscore 1-3 + 3CDP's + 3 CDM's = what I have left to do.

I would reconsider the note taking. I found my notes really helpful, especially for gen chem. I took notes my second time through his videos.

 

[free99]

I would reconsider the note taking. I found my notes really helpful, especially for gen chem. I took notes my second time through his videos.

I believe he's already taken the DAT, I just bumped this thread in case anyone else was puzzled by a few of these reactions 🙂 Good advice, nonetheless!

 

[tooth knockn]

Nice bump