(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
Want to see the full answer?
Check out a sample textbook solution
Chapter 11 Solutions
Essential Organic Chemistry, Global Edition
- Explain 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_forwardWhat 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_forward
- 4. WHAT ARE IMINES? HOW ARE THEY FORMED? 5. WHAT IS GRIGNARD REACTION? WHAT CONSTITUTES A GRIGNARD REAGENT? 6. WHAT IS KETO-ENOL TAUTOMERIZATION?arrow_forwardSpecify the reaction conditions to favour the indicated elimination mechanism. a. Strong base, such as hydroxide, an alkoxide, or equivalent b. Water or alcohol or equivalent weak base with heat c. Weak acid, such as formic acid, or equivalent d. Strong base, such as hydroxide, an alkoxide, or equivalentarrow_forwardWhat explains why many aldehydes and ketones can undergo self-condensation reactions in basic conditions? The alpha carbon can lose a proton and act like a nucleophile and the carbonyl carbon is an electrophile. The alpha carbon can gain a proton and act like an electrophile and the carbonyl carbon is a nucleophile. The oxygen of the carbonyl group can attack the carbon of the carbonyl group. Only esters can undergo self-condensation reactions.arrow_forward
- In the Friedel-Crafts alkylation of benzene, dialkylation is often a significant by-product. In the Friedel-Crafts acylation of benzene, diacylation is not a significant by-product. Which of the following is the primary reason for this difference? a. Acyl cations are more difficult to make with Lewis acids b.Unlike acyl cations, carbocations can undergo rearrangements. c.Alkyl groups activate the ring to further substitution, acyl groups deactivate it. d. Alkyl groups activate the ring to further substitution, acyl groups deactivate itarrow_forwardWhy aldehydes and ketones do not undergo nucleophilic substitution reaction?arrow_forwardFrom the Hammet equation data, it was observed that the nucleophilic substitution reaction of benzyl bromide and benzyl bromide with substituents at the ortho- and para-positions have shown a negative p value. Which of the following statements is/are True? A. The halide leaves before the nucleophile attacks the electrophilic site B. A concerted type of reaction has occurred. C. A decrease in electron density has occurred at the transition state D. An increase in electron density has occurred at the transition state E. A and Carrow_forward
- Which of the following is correct concerning a nucleophilic substitution reaction on an organic substrate (substitution on C atom)? Select one: A. The entering group is the Nucleophile and the carbon bearing the leaving group is the Electrophile. B. leaving group is the Nucleophile and entering group is the Electrophile. C. carbon bearing the leaving group is the Nucleophile and the leaving group is the Electrophile. D. entering group is the Electrophile and carbon bearing the leaving group is the Nucleophile.arrow_forwardWhat is the product of the reaction of bromoethane with each of the following nucleophiles?arrow_forwardWhat is the rate-determining step in the mechanism of an electrophilic substitution reaction of benzene? Select one: OA. Attachment of the electrophile to benzene ring. OB. Bonding of catalyst to electrophile precursor. O C. Reformation of acid catalyst. OD. Formation of the electrophile. OE. Loss of H+ ion form arenium ion intermediate to reform aromatic ring.arrow_forward
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning