Epoxide Opening with Acids, Bases and Grignards

Posted on December 7th, 2012

We here at StudyOrgo.com think it is very important to help students make connections when studying organic chemistry. When professors teach you about reactions, or you read a textbook about isolated reactions, one rarely picks up the underlying connection between related reactions. One reason that professors do not teach you these things is because it becomes a highly-testable concept that you have to “figure out on your own.” One of our main goals is to identify key connections and present them for you throughout our materials.

Take, the opening of an epoxide as an example. The reagent will attack an epoxide at varying parts of the substance depending on the type of reagent. For example, acids attack the most substituted position on the epoxide, bases attack the least substituted position and grignards also attack the least substituted position.

So here it is in plain, simple English:

  • Acid catalyzed epoxide ring opening: attack the most substituted position on the epoxide.
  • Base catalyzed epoxide ring opening: attack the least substituted position on the epoxide.
  • Grignard epoxide opening: attack the least substituted position on the epoxide

To review these key concepts with reaction examples, visit our reaction flashcard “Study Mode” (members only) which can be accessed from the account homepage.

Try:

1) Epoxides category- Epoxide Opening Reactions (7 reactions)

2) Alcohols category – Grignard Epoxide Opening Reaction

Then practice by creating your own custom quizzes by visiting our “Quiz Mode” homepage (members only also).

 

Think About Integrating Reactions

Posted on November 30th, 2012

December is the last month for organic chemistry courses for a lot of universities. So by entering the month of December – you are in the home stretch and you can sense the end is near. Most of you are probably very excited for that. At this point, try to begin integrating concepts as you approach possibly one of your last few exams or quizzes prior to the final exam.

You have learned many reactions at this point and likely feel that you have studied each relatively independant of the other. Now would be a good time to see if there are any similarities in between different reactions. This is especialy important because as you learn more, things start to blur a bit and seem to overlap with one another. That is because it does!

One good way to see how reaction relate to one another is to make lists. Some examples:

1) Make a list of all the possible ways you can make alkenes

2)  Make a list of all the possible ways you can make alkynes

3)  Make a list of all the things you can do with an alkene

4)  Make a list of all the things you can do with an alkyne

and so on…

Another way to integrate reactions is to draw out a map. Many students do not do this because it is extremely time intensive and cumbersome. Good new is that StudyOrgo.com has got you covered. Our team already has drawn out a beautifully color-coded Reaction Roadmap that illustrates these interconnections. StudyOrgo.com members have access to this by visiting:

http://www.studyorgo.com/roadmap.php

Not yet a member? No problem click here to sign-up.

Happy Integrating!

-The StudyOrgo.com Team

Reaction Intermediates: Radical, Carbocation, Carbanion

Posted on November 26th, 2012

It is important to know the hierarchy of Reaction Intermediates such as Radicals, Carbocations, Carbanions.
Here we present a quick guide to Reaction Intermediate hierarchies.
The Big Picture: Radicals and Carbocations prefer a greater degree of alkyl substitution. While, Carbanions are the opposite: Carbanions prefer a lesser degree of alkyl substitution. However, all three prefer the allylic position the most!
This is some of the information presented in Part 10 of our Study Guide: one of the many resources available to StudyOrgo.com members. Learn more about it here: How It Works.
    1. Allylic position
      1. Definition: The position immediately next to a double bond
      2. Image: The arrow points to the allylic position: 
    2. Reaction Intermediates
      • Radical
        • Typically electrons come in pairs. However there are unpaired electrons known as radical electrons. These are usually just called radicals.
        • Radical stability
          1. Radicals prefer a greater degree of alkyl substitution. Even more so, radicals prefer to be in the allylic position.
          2. Therefore here is the hierarchy of radical intermediate stability:

      • Carbocation
        • Carbocations serve as electrophiles in reactions. They will attract electrons easily as the carbon is deficient in electrons.
        • Carbocation stability
          1. Carbocations prefer a greater degree of alkyl substitution. Even more so, carbocations prefer to be in the allylic position. Therefore here is the hierarchy of carbocation intermediate stability:

      • Carbanion
        • Carbanions serve as nucleophiles in reactions. They will donate electrons easily as the carbon has excess electrons.
        • Carbanion stability
          1. Carbanions prefer a lesser degree of alkyl substitution. Even more so, carbanions prefer to be in the allylic position. Therefore here is the hierarchy of carbanion intermediate stability:

Join StudyOrgo.com today and save 10% using coupon code “acespring”.  We have the highest pass rate of any organic chemistry study program and we guarantee you pass.

Commonly Asked Infrared Spectroscopy Values

Posted on November 14th, 2012

Students are constantly looking for the most important information to know when studying organic chemistry. This is especially important when it comes to those pesky IR values. There are so many to know!

Question: Which IR values do I need to know?

Answer: The short answer- all of them. However, when studying these, it is helpful to start with the most important ones. Memorize these first, then learn the other ones.

For IR (Infrared Spectroscopy):

1) Very strong peak around 1700 = carbonyl group

2) Broad peak above 3000 = OH group in carboxylic acids, but be careful this could also just be a regular OH group in any alcohol

3) Just below 3000 = hydrogen on an alkane

4) Just over 3000 = hydrogen on an alkene

5) Sharp peak at around 3300 = hydrogen on an alkyne

For more help learning Infrared Spectroscopy and Nuclear Magnetic Resonance Spectroscopy values check out the StudyOrgo.com Infrared Spectroscopy and Nuclear Magnetic Resonance Spectroscopy Study Chart. To learn more about our program click here.

Organic Chemistry Quizzes Launch

Posted on November 5th, 2012

We are pleased to announce that Quiz Mode has officially launched and is now available for use. There is no need to download an update, all upgrades have been automatically incorporated into every account.

In addition to the launch of this new mode, a new Account Homepage has been created, in addition to other esthetic and functional upgrades throughout the site.
Here are some highlights:
1) Study Mode and Quiz Mode
We have now completed our transition to an overall method of having two main reaction flashcard modes: Study Mode and Quiz Mode.
Study Mode:
The original StudyOrgo.com flashcard system will now be known as Study Mode. It will remain as is with some tweaks including one major difference. All reaction flashcards windows will now be revealed at baseline to facilitate learning of all the information on the flashcard without having to reveal each area of the card. However, should you want to use Study Mode in its original manner, you may click on the “Study Flashcards Covered” checkbox found on any flashcard page to restore the system to its original fashion.
Quiz Mode:
You now have the ability to construct custom quizzes to test your knowledge of the material learned in Study Mode in our new Quiz Mode. You have options of choosing specific reaction categories, number of questions and the part of the reaction that you would like to be quizzed on among other items. Use the drawing space below the reaction to draw your response. When ready, click on the covered window to reveal the answer. Compare your response to the correct answer. Once you have mastered a particular reaction, you may mark it as “mastered” by checking the box found underneath the reaction. When you end a particular quiz, review your performace using our review page. The marked as mastered feature is maintained between the two modes. You can even exit and save quizzes and continue working later.

2) Account Homepage

Your new account homepage organizes the main features of the Study Mode and Quiz Mode into one neat dashboard.
  • Under the Study Mode section you can take advantage of helpful shortcuts such as recently viewed reactions, browse all reactions by name and review all reaction flashcards.
  • Under the Quiz Mode section you can jump to recent quizzes or create a new quiz.
  • There are also shortcuts to our additional materials such as the Summary Guide and Exercise Sets, Study Charts, and Reaction Roadmap.
Feel free to log in and browse the changes and take advantage of our new and improved program.