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Interpretation:
The reaction which occurs faster in each of the given reactions is to be determined and the reason is to be explained.
Concept introduction:
Alkyl iodides are several times more reactive than alkyl bromides. These reactivity differences can be related to the carbon-halogen bond strength and the basicity of the halide anion. Alkyl iodides have the weakest carbon-halogen bond and require the lowest activation energy to break.
Regarding basicity of the halide leaving the group, iodide is the weakest base. Generally, it is true that, the less basic the leaving group, the smaller the energy requirement for cleaving its bond to carbon and the faster the rate.
Alkyl groups that are adjacent to the carbon atom to the point of nucleophilic attack decrease the rate of the
Protic solvents having
In
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Answer to Problem 27P
Solution:
a)
b)
c) Cyclohexyl chloride reacts faster than hexyl chloride by the
d) Tert-butyl bromide reacts faster than
e) sec-butyl bromide reacts faster than isobutyl bromide by the
f) The reaction of
g) The reaction of
Explanation of Solution
a)
Both the given
b)
Both the given alkyl halides are primary alkyl halides. The reagent is sodium iodide in acetone. Both these suggest an
c)
Hexyl chloride is a primary alkyl halide whereas cyclohexyl chloride is a secondary alkyl halide. The solvent is ethanol, which is a polar protic solvent. The nucleophile is the azide ion, which is a good nucleophile. Solvation of the azide ion by ethanol reduces the rate of bimolecular substitution. Polar protic solvents favor
d)
The solvent is ethanol, which is a polar protic solvent. It favors the
e)
The solvent is aqueous formic acid, which is a polar protic solvent. It favors the
f)
As long as the nucleophilic atom is the same, the more basic the nucleophile, the more reactive it is. The methoxide ion is more basic and more nucleophilic than the acetate ion. Thus, the reaction of
g)
Comparing the nucleophilic atoms, the azide ion is more nucleophilic than the p-toluene sulfonate ion since nitrogen is less electronegative than oxygen. Thus, the reaction of
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Chapter 6 Solutions
ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE
- if the answer is no reaction than state that and please hand draw!arrow_forward"I have written solutions in text form, but I need experts to rewrite them in handwriting from A to Z, exactly as I have written, without any changes."arrow_forwardDon't used hand raiting and don't used Ai solutionarrow_forward
- Please correct answer and don't used hand raitingarrow_forwardreciprocal lattices rotates along with the real space lattices of the crystal. true or false?arrow_forwardDeducing the reactants of a Diels-Alder reaction vn the molecule on the right-hand side of this organic reaction be made in good yield from no more than two reactants, in one step, by moderately heating the reactants? ? Δ O If your answer is yes, then draw the reactant or reactants in the drawing area below. You can draw the reactants in any arrangement you like. • If your answer is no, check the box under the drawing area instead. Click and drag to start drawing a structure. Product can't be made in one step. Explanation Checkarrow_forward
- Predict the major products of the following organic reaction: Δ ? Some important notes: • Draw the major product, or products, of the reaction in the drawing area below. • If there aren't any products, because no reaction will take place, check the box below the drawing area instead. • Be sure to use wedge and dash bonds when necessary, for example to distinguish between major products that are enantiomers. Explanation Check Click and drag to start drawing a structure. Larrow_forward> Can the molecule on the right-hand side of this organic reaction be made in good yield from no more than two reactants, in one step, by moderately heating the reactants? ? Δ • If your answer is yes, then draw the reactant or reactants in the drawing area below. You can draw the reactants in any arrangement you like. If your answer is no, check the box under the drawing area instead. Explanation Check Click and drag to start drawing a structure. Х © 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Center | Accesarrow_forwardPredict the major products of the following organic reaction: O O + A ? Some important notes: • Draw the major product, or products, of the reaction in the drawing area below. • If there aren't any products, because no reaction will take place, check the box below the drawing area instead. • Be sure to use wedge and dash bonds when necessary, for example to distinguish between major products that are enantiomers. Explanation Check Click and drag to start drawing a structure. eserved. Terms of Use | Privacy Center >arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
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