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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?
Aprotic solvent
Unimolecular reaction kinetics
Formation of a carbocation intermediate
Weak base
Tertiary substrate
Aprotic solvent
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?
Two-step mechanism
Bimolecular reaction kinetics
Tertiary substrate
Strong base
Aprotic solvent
Two-step mechanism
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?
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?
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?
IV
III
II
I
III
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?
II only
I and II
I, II, and III
I only
III only
II only
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?
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
Classify the type of reaction given.
Substitution
Addition
Elimination
Rearrangement
Elimination
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
Classify the type of reaction given.
Homolytic bond breaking
Substitution
Heterolytic bond breaking
Addition
Heterolytic bond breaking
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
Classify the type of reaction given.
Homolytic
Addition
Catalysis
Elimination
Elimination
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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