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Interpretation:
Whether methoxide ion is a better nucleophile in
Concept Introduction:
Aprotic solvent are polar solvent molecules which do not have hydrogen bonded to oxygen to nitrogen.
The stronger base is always a better nucleophile in an aprotic solvent. When the negatively charged species is placed in aprotic solvent, the solvent molecules arrange themselves with their partially positively charged hydrogens pointing towards the negatively charged species. The interaction between the ion and the dipole of the protic solvent is called an ion-dipole interaction
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Chapter 9 Solutions
Organic Chemistry; Modified MasteringChemistry with Pearson eText -- ValuePack Access Card; Study Guide and Student Solutions Manual for Organic Chemistry, Books a la Carte Edition (7th Edition)
- Consider the following groups of compounds. In each series circke the weaker (poorer) nucleophile. Please explain why.arrow_forwardExplain why a methoxy group (CH3O) increases the rate of electrophilic aromatic substitution, but decreases the rate of nucleophilic aromatic substitution.arrow_forwardPredict whether the following nucleophiles are excellent nucleophiles, good nucleophiles, or poor nucleophiles based on their structure, and sort them accordingly.arrow_forward
- Explain why quinuclidine is a much more reactive nucleophile than triethylamine, even though both compounds have N atoms surrounded by three R groups.arrow_forwardHow does the strength of the nucleophile affect an SN1 or SN2 mechanism?arrow_forwardWhich is the strongest nucleophile among the following? CN- , OH-, CH3OH, NH3arrow_forward
- I labeled one of the atoms incorrectly, but I am not sure which. Would the H in HBr be considered a nucleophile as well ?arrow_forward2. Draw the structures and explain why CH3CH₂O and CH3CO₂ are good nucleophiles but CH3SO3, water, and alcohols (R-OH) are poor nucleophiles. Propose a 'cutoff' for the amount of negative charge needed to be a good nucleophile. CH3CH₂O CH3CO₂ CH3SO3 H₂O CH₂OHarrow_forwardIn order to complete the synthesis shown below, you would need to use [ Select ] as the nucleophile source and [Select] as the solvent. H3C OH H3C Br H3CY CH3 H3C CH3arrow_forward
- rank these from least to most reactive in nucleophilic acyl substitution with a nucleophile I)CH3COOC2H5 II) CH3COO-Na+ III)CH3COCl IV) CH3CONH2arrow_forwardThe reaction of an alkyl chloride with potassium iodide is generally carried out in acetone to maximize the amount of alkyl iodide that is formed. Why does the solvent increase the yield of alkyl iodide? (Hint: Potassium iodide is soluble in acetone, but potassium chloride is not.)arrow_forwardWhich of the following is more likely to act as a nucleophile than a base? O DBU DBNarrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage LearningEBK A SMALL SCALE APPROACH TO ORGANIC LChemistryISBN:9781305446021Author:LampmanPublisher:CENGAGE LEARNING - CONSIGNMENT
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