Organic Chemistry : Organic Concepts

Study concepts, example questions & explanations for Organic Chemistry

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Example Questions

Example Question #3 : Help With Elimination Reactions

Which of the following characteristics does not reflect an E1 reaction mechanism?

Possible Answers:

Aprotic solvent

Unimolecular reaction kinetics

Formation of a carbocation intermediate

Weak base

Tertiary substrate

Correct answer:

Aprotic solvent

Explanation:

E1 reactions occur in two steps, forming a carbocation intermediate, which is most stable if there is a protic solvent present. Furthermore, the use of a weak base favors E1.

Example Question #4 : Help With Elimination Reactions

Which of the following characteristics does not reflect an E2 reaction mechanism?

Possible Answers:

Two-step mechanism

Bimolecular reaction kinetics

Tertiary substrate

Strong base

Aprotic solvent

Correct answer:

Two-step mechanism

Explanation:

E2 reactions occur in one step; thus no carbocation intermediate is formed, and an aprotic solvent is favored. E2 reactions are favored by strong bases and higher temperatures.

Example Question #4 : Help With Elimination Reactions

The molecule shown reacts with . Which type of reaction will ensue?

Possible Answers:

Correct answer:

Explanation:

These conditions are perfect for an  reaction. We see a secondary halide so first instinct might be to say that an  reaction would ensue. However, anytime we have a secondary halide reacting with a strong, bulky base, the laws of sterics dictates that an  reaction will ensue.

Example Question #7 : Help With Elimination Reactions

Chloropropane reacts with   to form propene.

Through which mechanism did this reaction occur?

Possible Answers:

Correct answer:

Explanation:

The given conditions are perfect for an  reaction. Here we have a primary haloalkane reacting with a big, bulky base. Big, bulky bases such as , and alkene products are classic indicators that the reaction was an  reaction.

Example Question #5 : Help With Elimination Reactions

Which of the following hydrogens are removed upon treatment of the pictured molecule with potassium tert-butoxide?

Screen shot 2015 11 09 at 3.15.31 pm

Possible Answers:

IV

III

II

I

Correct answer:

III

Explanation:

Treatment with strong base indicates E2 mechanism. The halide has two beta-carbons (II and III), and potassium tert-butoxide is a bulky base. The favored product is the Hofmann product (less substituted alkene). Therefore III is the hydrogen that's removed. 

Example Question #6 : Help With Elimination Reactions

What is the product of the reaction shown?

 Screen shot 2015 11 14 at 10.45.18 am

Screen shot 2015 11 14 at 10.41.22 am

Possible Answers:

II only

I and II

I, II, and III

I only

III only

Correct answer:

II only

Explanation:

E2 reaction mechanism requires antiperiplanar orientation between the leaving group and the hydrogen. Given the stereochemistry of the methyl group, forming an alkene bond (to give the more substituted product) is impossible.

Example Question #9 : Help With Elimination Reactions

What is the major product in the following reaction?

Image2

Possible Answers:

Correct answer:

Explanation:

This is an acid-catalyzed dehydration of a tertiary alcohol. The first step is protonation of the alcohol oxygen which will create a good leaving group (), and subsequent loss of water from the molecule. The molecule will then contain a carbocation (which will not move due to the positive being on the most substituted carbon atom in its immediate vicinity), and the conjugate base (water in this case) will remove a hydrogen from a carbon next to the carbocation. The base will preferentially remove a hydrogen from the one that will produce the more substituted alkene, as this is generally the more stable product. This is known as Zaitsev's rule for the formation of alkenes.

Example Question #61 : Organic Concepts

Screen shot 2016 02 21 at 6.39.46 am

 Classify the type of reaction given.

Possible Answers:

Substitution

Addition

Elimination

Rearrangement

Correct answer:

Elimination

Explanation:

An elimination reaction occurs when there is a release of atoms in a given compound to produce two or more products. In the reaction given a hydrogen and chloride atom are eliminated from the original compound to form hydrochloric acid and ethylene.

Example Question #62 : Organic Concepts

Screen shot 2016 02 21 at 7.20.17 am

 Classify the type of reaction given.

Possible Answers:

Homolytic bond breaking

Substitution

Heterolytic bond breaking

Addition

Correct answer:

Heterolytic bond breaking

Explanation:

Heterolytic bond breaking occurs in polar compounds to form to products of opposite charges. In these types of reaction two electrons from the original bond stays with one fragment upon cleavage. In the reaction given, the bond between the hydrogen and chlorine atom is broken with the two electrons from the original bond staying with the chlorine atom. The resulting products are hydrogen ion and chloride ion. 

 

Example Question #63 : Organic Concepts

Screen shot 2016 02 21 at 7.20.05 am

 Classify the type of reaction given.

Possible Answers:

Homolytic

Addition

Catalysis

Elimination

Correct answer:

Elimination

Explanation:

An elimination reaction occurs when there is a release of atoms in a given compound to produce two or more products. In the reaction given a hydrogen and chloride atom are eliminated from the original compound to form one 2-butene, potassium chloride and water molecule.

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