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InvisibleCapers
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Organic Chemistry Homework Enigma
    #18903973 - 09/28/13 06:40 PM (10 years, 4 months ago)

This assignment has already eaten hours and hours of my life. I have answered 43 of 48 questions correctly. Could someone please help me?



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Offlinemellowparty
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Re: Organic Chemistry Homework Enigma [Re: Capers]
    #18909799 - 09/30/13 02:32 AM (10 years, 3 months ago)



Anhydrous CrO3 oxidizes primary alcohols to aldehydes unlike Jones reagent which takes it to the respective carboxylic acid. I've marked the stereocenters with a squiggle.


Post moar problems :gameover: shit's fun :takingnotes:


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InvisibleCapers
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Re: Organic Chemistry Homework Enigma [Re: mellowparty]
    #18910211 - 09/30/13 07:25 AM (10 years, 3 months ago)

Wow, killer job! You got them all right. Here's how my homework program drew out the molecules:



I think they are exactly the same as your solutions.


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Offlinemellowparty
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Re: Organic Chemistry Homework Enigma [Re: Capers]
    #18910247 - 09/30/13 07:37 AM (10 years, 3 months ago)

Yup, they're the same.


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InvisibleCapers
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Re: Organic Chemistry Homework Enigma [Re: mellowparty]
    #18910250 - 09/30/13 07:38 AM (10 years, 3 months ago)

Well done. When did you take Orgo?


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InvisibleCapers
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Re: Organic Chemistry Homework Enigma [Re: mellowparty]
    #19009118 - 10/21/13 03:40 PM (10 years, 3 months ago)

I've got a new problem for you:



hint: Base reacts with carbonyl compounds to form an enolate ion, provided an α-hydrogen is available.

hint 2: The hydroxide ion can remove a proton from a carbon in an α -position to the carbonyl, producing an enolate anion. There are no α-hydrogens adjacent to the aldehyde group, but there are two α-hydrogens on each carbon adjacent to the ketone group. Which carbon will lose a proton? The resulting nucleophilic site will attack the electrophilic carbonyl carbon. We know from the formula that the product is not a dimer. The reaction will follow the path that will result in a stable compound.


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Invisiblejohnm214
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Re: Organic Chemistry Homework Enigma [Re: Capers]
    #19009348 - 10/21/13 04:35 PM (10 years, 3 months ago)



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OfflineTwinEclipse
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Re: Organic Chemistry Homework Enigma [Re: johnm214]
    #19012436 - 10/22/13 07:51 AM (10 years, 3 months ago)

Lucky. I don't understand any of that mumbo jumbo.

I will understand after next semester :awehigh:


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Offlineimachavel
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Re: Organic Chemistry Homework Enigma [Re: mellowparty]
    #19012753 - 10/22/13 09:33 AM (10 years, 3 months ago)

Quote:

mellowparty said:


Anhydrous CrO3 oxidizes primary alcohols to aldehydes unlike Jones reagent which takes it to the respective carboxylic acid. I've marked the stereocenters with a squiggle.


Post moar problems :gameover: shit's fun :takingnotes:




I barely understand chemistry but shit is so awesome to read. Oxidizing a molecule means an oxygen atom is added to the chain right? What is the ph of each one of those molecules? How does oxidizing effect the ph? And furthermore how does oxidizing effect the polarity?


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InvisibleCapers
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Re: Organic Chemistry Homework Enigma [Re: johnm214]
    #19014355 - 10/22/13 03:53 PM (10 years, 3 months ago)

Quote:

johnm214 said:





Thanks a lot! That was right. Anyone wanna take a stab at this one:



hint: Ethoxide ion is a base that can remove an acidic proton in an α-position to a carbonyl group, producing a nucleophilic enolate ion. Locate the α-hydrogens in the given molecule. What enolate ions can be formed in this reaction mixture?

hint 2: In the given structure there are two α-carbons that can lose a proton; therefore, two enolates are possible. To determine which enolate will yield the major product in this reaction, you need to consider the reaction mechanism. Compare the molecular formulas of the reactant and product. What does it tell you about the reaction? Which electrophilic site does the enolate attack?


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Invisiblejohnm214
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Re: Organic Chemistry Homework Enigma [Re: Capers]
    #19016331 - 10/22/13 09:22 PM (10 years, 3 months ago)

I think it would be this:



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