a)
Interpretation:
Whether N,N-dimethylamino group is an activator or deactivator and whether it is a o-, p-director or m-director is to be stated.
Concept introduction:
In
Electron releasing groups, except halogens, normally are activators and ortho & para directors. Electron withdrawing groups normally are deactivators and meta directors. Halogens are ortho & para directing but are deactivating.
To state:
Whether N,N-dimethylamino group is an activator or deactivator and whether it is a, o-, p-director or m-director.
b)
Interpretation:
Whether cyclopentyl group is an activator or deactivator and whether it is an o-, p-director or m-director is to be stated.
Concept introduction:
In aromatic substitution reactions the activating or deactivating and orienting effects of a substituent attached to the benzene ring can be decided from its resonance and inductive effects. The orientation is decided by the resonance effect while the activating or deactivating effect is decided both by resonance and inductive effects. Both effects may reinforce or oppose each other. However the resonance effect is much stronger than the inductive effect.
Electron releasing groups, except halogens, normally are activators and ortho & para directors. Electron withdrawing groups normally are deactivators and meta directors. Halogens are ortho & para directing but are deactivating.
To state:
Whether cyclopentyl group is an activator or deactivator and whether it is an o-, p-director or m-director.
c)
Interpretation:
Whether ethoxy group is an activator or deactivator and whether it is an o-, p-director or m-director is to be stated.
Concept introduction:
In aromatic substitution reactions the activating or deactivating and orienting effects of a substituent attached to the benzene ring can be decided from its resonance and inductive effects. The orientation is decided by the resonance effect while the activating or deactivating effect is decided both by resonance and inductive effects. Both effects may reinforce or oppose each other. However the resonance effect is much stronger than the inductive effect.
Electron releasing groups, except halogens, normally are activators and ortho & para directors. Electron withdrawing groups normally are deactivators and meta directors. Halogens are ortho & para directing but are deactivating.
To state:
Whether ethoxy group is an activator or deactivator and whether it is an o-, p-director or m-director.
d)
Interpretation:
Whether the carbonyl group is an activator or deactivator and whether it is a o-, p-director or m-director is to be stated.
Concept introduction:
In aromatic substitution reactions the activating or deactivating and orienting effects of a substituent attached to the benzene ring can be decided from its resonance and inductive effects. The orientation is decided by the resonance effect while the activating or deactivating effect is decided both by resonance and inductive effects. Both effects may reinforce or oppose each other. However the resonance effect is much stronger than the inductive effect.
Electron releasing groups, except halogens, normally are activators and ortho & para directors. Electron withdrawing groups normally are deactivators and meta directors. Halogens are ortho & para directing but are deactivating.
To state:
Whether carbonyl group is an activator or deactivator and whether it is a o-, p-director or m-director.
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Chapter 16 Solutions
Organic Chemistry
- Identify the reagents represented by the letters a-e in the following scheme:arrow_forwardThe Stork reaction is a condensation reaction between an enamine donor and an α,β-unsaturated carbonyl acceptor. The overall reaction consists of a three-step sequence of formation of an enamine from a ketone, Michael addition to an α,β-unsaturated carbonyl compound, and hydrolysis of the enamine in dilute acid to regenerate the ketone. Consider the Stork reaction between cyclohexanone and propenal Draw the structure of the product of the enamine formed between cyclohexanone and dimethylamine. - Michael addition to an α,β-unsaturated carbonyl compound, and - hydrolysis of the enamine in dilute acid to regenerate the ketone.arrow_forward2) a) n-Butyllithium is used to deprotonate the following compounds. Draw the structures of the resulting organolithium compounds (assume they are monomeric). Me₂N SO₂ b) Explain the selectivity of deprotonation. c) Each organolithium is reacted with ethyltosylate. Draw the structures of the resulting products.arrow_forward
- Identify the major product.arrow_forwardConsider the folowing synthetic target. Propose a suitable starting material and reagents to effect the reaction and clearly outline the mechanism by which the reaction takes place. In your answer, show how the intermediate ion is stabilized.arrow_forwardProvide a structure for A and a detailed mechanism for the following transformation. pka pka H3C CH3 NaOEt A CH3Li tBu + tBuarrow_forward
- Verapamil, a coronary artery vasodilator, is used in the treatment of angina caused by insufficient blood flow to cardiac muscle. Even though its effect on coronary vasculature tone was recognized over 30 years ago, only recently has its role as a calcium channel blocker become understood. Following is a retrosynthetic analysis leading to a convergent synthesis; it is convergent because (A) and (B) are made separately and then combined (i.e., the route converges) to give the final product. Convergent syntheses are generally much more efficient than those in which the skeleton is built up stepwise. Q. Two steps are required to convert (D) to (C). The first is treatment of (D) with ethyl chloroformate. What is the product of this first step? What reagent can be used to convert this product to (C)?arrow_forwardVerapamil, a coronary artery vasodilator, is used in the treatment of angina caused by insufficient blood flow to cardiac muscle. Even though its effect on coronary vasculature tone was recognized over 30 years ago, only recently has its role as a calcium channel blocker become understood. Following is a retrosynthetic analysis leading to a convergent synthesis; it is convergent because (A) and (B) are made separately and then combined (i.e., the route converges) to give the final product. Convergent syntheses are generally much more efficient than those in which the skeleton is built up stepwise. Q. How do you account for the regioselectivity of the nucleophilic displacement involved in converting (C) to (B)?arrow_forwardPROBLEM Identify each of the following groups as an activator or deactivator and as an o,p-director or m- 16-46 director: (a) (b) (c) (d) -N(CH3)2 OCH₂CH3 Oarrow_forward
- Predict the MAJOR product by proposing a plausible mechanism. Indicate stereochemistry when applicable. NaH Et .arrow_forwardThe Stork reaction is a condensation reaction between an enamine donor and an α,β-unsaturated carbonyl acceptor. The overall reaction consists of a three-step sequence of formation of an enamine from a ketone, Michael addition to an α,β-unsaturated carbonyl compound, and hydrolysis of the enamine in dilute acid to regenerate the ketone. Consider the Stork reaction between acetophenone and 3-buten-2-one. Draw the structure of the product of the enamine formed between acetophenone and pyrrolidine. Draw the structure of the Michael addition product. Draw the structure of the final product.arrow_forwardPropose a mechanism for this isomerization. ARSO3Harrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage LearningOrganic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning