(a)
Interpretation: To identify the products of following reactions when new groups in tetrahedral intermediate is a stronger base than the group that attached group in acyl group.
Concept introduction: The
The basicity comparison can be done by using the
(b)
Interpretation: To identify the products of following reactions when new groups in tetrahedral intermediate is a weaker base than the group that attached group in acyl group.
Concept introduction: The carboxylic acid and its derivatives undergo nucleophilic acyl substitution reaction. The incoming group is called as nucleophile and the substituent that departs from molecule is known as leaving group. If the attacking group is a good base as compared to the substiuent that is already present than attacking group will replace the existing substituent.
The basicity comparison can be done by using the
(c)
Interpretation: To identify the products of following reactions when new groups in tetrahedral intermediate is similar in basicity to the group that attached group in acyl group
Concept introduction: The carboxylic acid and its derivatives undergo nucleophilic acyl substitution reaction. The incoming group is called as nucleophile and the substituent that departs from molecule is known as leaving group. If the attacking group is a good base as compared to the substiuent that is already present than attacking group will replace the existing substituent.
The basicity comparison can be done by using the
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Chapter 11 Solutions
Essential Organic Chemistry, Global Edition
- For each horizontal row of substituted benzenes, indicate a. the one that is the most reactive in an electrophilic aromatic substitution reaction. b. the one that is the least reactive in an electrophilic aromatic substitution reaction. c. the one that yields the highest percentage of meta product in an electrophilic aromatic substitution reaction.arrow_forwardExplain why a nucleophilic reagent such as ethoxide adds to an alkyne more easily than it adds to an alkenearrow_forward10. Why do aldehydes undergo nucleophilic addition reactions (rxns from Unit 10) while esters undergo nucleophilic acyl substitution (rxns from Unit 11) reactions? A) The carbonyl carbon of an ester is more electrophilic than that of an aldehyde. B) Aldehydes are more sterically hindered than esters. C) Once the nucleophile adds to an aldehyde, the tetrahedral intermediate is too sterically hindered to eliminate one of the attached groups. D) The ester carbonyl carbon is sp3 hybridized while the aldehyde carbonyl carbon is sp2 hybridized. E) Once the nucleophile adds to an aldehyde, neither H- nor R- can be eliminated since they are strongly basic.arrow_forward
- What is the importance of proton transfer in the formation of ester? A.The carbonyl carbon is easily attacked by the nucleophile. B. The oxygen that has been attached to the two alkyl groups will become stable. C. The removal of a bulky substituent attached to the reactive site stabilizes the compound. D. none of the abovearrow_forwardFor each horizontal row of substituted benzenes, indicatea. the one that is the most reactive in an electrophilic aromatic substitution reaction.b. the one that is the least reactive in an electrophilic aromatic substitution reaction.c. the one that yields the highest percentage of meta product in an electrophilic aromatic substitution reaction.arrow_forwardexplain why carbonyl compounds are so attractive to both nucleophiles and electrophilesarrow_forward
- 4arrow_forwardWhich of the following molecules is antiaromatic? A. cyclopentadienyl anion B. cyclopentadiene C. cycloheptatrien D. Cyclopentadienyl cation E. cycloheptatrienyl cationarrow_forwardDoes doubling the concentration of an alkylhalide and maintaining the alkoxide concentration double the reaction rate? What if the alkylhalide concentration is maintained and the alkoxide concentration is doubled?arrow_forward
- See image belowarrow_forwardA. Draw the products of the reaction shown below. Use wedge and dish bonds to indicate the dicarbonyl starting material of the reaction shown below. Ignore inorganic stereochemistry. Ignore inorganic byproducts. byproducts. Draw the products resulting from addition of a Grignard reagent to an aldehyde. D. Draw the products resulting from addition of a Grignard reagent to an aldehydom Use a dash or wedge bond to indicate the stereochemistry of substituents on asymmetric centers, where applicablelgnore any inorganic byproducts. Use a dash or wedge bond to indicate the stereochemistry of substituents on asymmetric centers, where applicablelgnore any inorganic byproducts. 1.00 2. NHSO HO 2.HO Select to Draw 1) PhMgCl (CHMgC CH 2) HCI/H:O ++ 1) vinylmagnesium chloride (CH=CHC 2HC/H.O Select to Edit OH Select to Edit Select to Edearrow_forwardDraw the structure of the product of the Michael reaction between propenamide and diethyl malonatearrow_forward
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning