Interpretation:
From the structure of the alkoxide ion represented by the model, formed by the addition of a nucleophile to a
Concept introduction:
Esters are hydrolysed to carboxylic acids and alcohols both in the presence of acid and base catalysts. The base catalysed hydrolysis takes place in three steps i) The nucleophilic attack of the base on the ester carbonyl group ii) Elimination of the leaving group iii) Exchange of protons.
To identify:
From the structure of the alkoxide ion represented by the model, formed by the addition of a nucleophile to a carboxylic acid derivative, the nucleophile, the leaving group, the starting acid derivative and the ultimate product.
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Chapter 21 Solutions
Organic Chemistry
- 1) Nucleophilic substitution reaction of alkyl halide is a process when nucleophile replace the leaving group of alkyl halide. Propose the mechanism and product(s) for the following substitution reaction.arrow_forwardDefine the following terms Homolytic bond breakage: Nucleophilearrow_forwardBr Brz CH3 CH3 H3C CH2CI2 H3C Br Electrophilic addition of bromine, Br2; to alkenes yields a 1,2-dibromoalkane. The reaction proceeds through a cyclic intermediate known as a bromonium ion. The reaction occurs in an anhydrous solvent such as CH,Cl). In the second step of the reaction, bromide is the nucleophile and attacks at one of the carbons of the bromonium ion to yield the product. Due to steric clashes, the bromide ion always attacks the carbon from the opposite face of the bromonium ion so that a product with anti stereochemistry is formed. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Br: :Br: .CH3 H3C H3C CH3 Br:arrow_forward
- What is the source of the nucleophilic attack? How does the oxygen get protonated? What causes the elimination reaction?arrow_forwardAn electron-deficient carbon atom reacts with a nucleophile, symbolized as: Nu−. Define this ?arrow_forwardExplain why pentane-2,4-dione forms two alkylation products (A and B) when the number ofequivalents of base is increased from one to two.arrow_forward
- What will be the product of the following reactions? Draw the Lewis-acid base reaction (including the arrows indicating the movement of electron pairs). Label which molecule is the nucleophile and which is the electrophile.arrow_forwardWrite a mechanism that accounts for the formation of ethyl isopropyl ether as one of the products in the following reaction. CI OEt HCI EtOH Write the mechanism for step one of this reaction. Show lone pairs and formal charges. Only the acidic hydrogen should be drawn out with a covalent bond. Write the mechanism for step two of this reaction (where the product of step one reacts with the solvent, ethanol). Show lone pairs and formal charges. Only the acidic hydrogen should be drawn out with a covalent bond. Write the mechanism for the last step of this reaction (formation of ethyl isopropyl ether). Show lone pairs and formal charges. Only the acidic hydrogen should be drawn out with a covalent bond. CI will act as the base in this reaction.arrow_forwardb) The Wolf-Kishner reduction is a reaction used in Organic Chemistry to convert carbonyl functionalities into methylene group. The reaction was used to convert an aldehyde or ketone to an alkane using hydrazine, base and thermal conditions. The mechanism begins with the attack of hydrazine of the aldehyde or ketone. Stage 1: The reaction of aldehyde/ketone with hydrazine to produce hydrazine Stage 2: Reaction with the base and heat to convert hydrozone to alkane Write the mechanism of the reaction.arrow_forward
- Predict the product formed in the nucleophilic aromatic substitution reaction between 1-chloro-2,4-dinitrobenzene and sodium methoxide (NaOCH3). Draw the mechanism for the reaction, showing why the product you have selected is formed.arrow_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 a an electrophile O The alpha carbon can gain a proton and act like an electrophile and the carbonyl carbon is a nucleophile O The oxygen of the carbonyl group can attack the carbon of the carbonyl group Only esters can undergo self-condensation reactionsarrow_forward2 H3C H3C H C→XT OH H3C The aldol reaction is a carbonyl condensation reaction between two carbonyl partners and involves a combination of nucleophilic addition and a-substitution steps. One partner is converted into an enolate ion nucleophile and adds to the electrophilic carbonyl group of the second partner. In the classic aldol reaction, the carbonyl partners are aldehydes or ketones, although aldehydes are more reactive. The product is a ß-hydroxy carbonyl compound. base :0: OH H H Under reaction conditions slightly more vigorous than those employed for the aldol reaction, the ß-hydroxyl group is eliminated in an E1cB dehydration to give an a,ß-unsaturated carbonyl compound. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instruct ns H3C heat OH H3C :0: H + H₂O Harrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning