Concept explainers
Interpretation:
It is to be determined which of the two nucleophiles
Concept introduction:
The strength of a nucleophile, particularly a negatively charged one, is considerably influenced by the nature of the solvent. A protic solvent interacts strongly with a negatively charged nucleophile as the solvent molecule contains at least one hydrogen that has a partial positive charge.
An aprotic solvent in which the atom with a partial positive charge is generally shielded by adjacent groups does not solvate the nucleophile as effectively.
The effective strength of a nucleophile depends on the extent of solvation as strong solvation prevents it from directly approaching the reaction center in the substrate. A number of solvent molecules from its solvation sphere must be lost before it can approach the reaction center close enough to form a bond.
Want to see the full answer?
Check out a sample textbook solutionChapter 9 Solutions
Organic Chemistry: Principles and Mechanisms (Second Edition)
- Good nucleophiles that are weak bases favor substitution overelimination. Explain this ?arrow_forwardFrom each pair, select the stronger nucleophile. Q.) CH3SH or CH3S-arrow_forwardWhich is the better nucleophile in a protic solvent, chloride ion or bromide ion? Try to explain this in terms of the nature of the chloride ion and the bromide ion.arrow_forward
- Identify the stronger nucleophile in the following pair of anions. Br− or Cl− in a polar protic solventarrow_forwardFrom each pair, select the stronger nucleophile. Q.)Cl2 or I2 in methanolarrow_forwardHi, Why is the OH on the enantiomers drawn with a wedged line instead of a dashed line? I was under the impression that if the leaving group was wedged then the nucleophile would be dashed.arrow_forward
- Which rearrangement product will form preferentially during the [1,2]-rearrangementof an R-group? Motivate.arrow_forwardWhich nucleophile would prefer simple addition over conjugate addition? CH3MgBr NaCN CH3CH2NH2 (CH3CH2)2CuLiarrow_forwardI labeled one of the atoms incorrectly, but I am not sure which. Would the H in HBr be considered a nucleophile as well ?arrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage LearningEBK A SMALL SCALE APPROACH TO ORGANIC LChemistryISBN:9781305446021Author:LampmanPublisher:CENGAGE LEARNING - CONSIGNMENT