Interpretation:
The nucleophile in the reaction of an aldehyde or ketone with a Grignard reagent is to be identified, and the function of magnesium in the Grignard reagent and the product formed initially and after water is added are to be determined.
Concept Introduction:
>Electrophiles are electron deficient species which has positive or partially positive charge. Lewis acids are electrophiles which accept electron pair.
>Nucleophiles are electron rich species which has negative or partially negative charge. Lewis bases are nucleophiles which donate electron pair.
>Nucleophilic addition reaction is an addition reaction where electron deficient or electrophilic double or triple bond reacts with electron rich species (nucleophile), with disappearance of the double bond and creation of two single bonds.
>The Grignard reagent or RMgX is a polar organometallic reagent that undergoes nucleophilic addition reaction with
In nucleophilic addition, the negative part of the attacking reagent goes to electron deficient carbon and gets attached. The addition product then undergoes elimination to form the final product.
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Organic Chemistry
- (a) Account for the following :(i) Propanal is more reactive than propanone towards nucleophilic reagents.(ii) Electrophilic substitution in benzoic acid takes place at meta position.(iii) Carboxylic acids do not give characteristic reactions of carbonyl group.(b) Give simple chemical test to distinguish between the following pairs of compounds:(i) Acetophenone and benzaldehyde(ii) Benzoic acid and ethylbenzoate.arrow_forwardProvide reagentsarrow_forwardComplete the following proposed acid–base reactions, and predict whether the reactants or products are favored.arrow_forward
- Consider the following structural formulas. OH H;C CH3 CH3 F G H (a) Which of the compounds F-l can easily be subjected to an elimination reaction? (b) Provide the reaction mechanism for all eliminations under (a).arrow_forwardWhen ethyl bromide is added to potassium tert-butoxide, the product is ethyl tert-butyl ether.(a) What happens to the reaction rate if the concentration of ethyl bromide is doubled?arrow_forward(a) Write the chemical reaction involved in Wolff-Kishner reduction.(b) Arrange the following in the increasing order of their reactivity towards nucleophilic addition reaction:C6H5COCH3, CH3— CHO, CH3COCH3(c) Why carboxylic acid does not give reactions of carbonyl group?arrow_forward
- Write the structure for the major product of the following reaction.arrow_forward2. (a) Ozonolysis of compound A, C,H12 gave two products B and C. Further analysis of these two compounds of B and C, showed positive results with 2,4-dinitrophenylhydrazine. Compound B reacts with Tollens' reagent while compound C does not indicate any positive result to the same reagent. However, both B and C gave same positive results with iodoform test. (i) By writing all the chemical equations involved, identify A, B and C.arrow_forwardWhen tert-butyl bromide is heated with an equal amount of ethanol in an inert solvent, one of the products is ethyl tert-butyl ether. (a) What happens to the reaction rate if the concentration of ethanol is doubled?arrow_forward
- (a) How will you obtain the following :(i) Benzaldehyde from Phenol (ii) Benzoic acid from Aniline(b) Give reasons :(i) Aldehydes are more reactive than ketones towards nucleophilic reagents.(ii) Electrophilic substitution in benzoic acid takes place at meta position.(iii) Carboxylic acids do not give the characteristic reactions of carbonyl group.arrow_forwardThe following questions concern ethyl (2-oxocyclohexane)carboxylate.(a) Write a chemical equation showing how you could prepare ethyl (2-oxocyclohexane)-carboxylate by a Dieckmann cyclization.(b) Write a chemical equation showing how you could prepare ethyl (2-oxocyclohexane)-carboxylate by acylation of a ketone.(c) Write structural formulas for the two most stable enol forms of ethyl (2-oxocyclohexane)carboxylate.(d) Write the three most stable resonance contributors to the most stable enolate derived from ethyl (2-oxocyclohexane)carboxylate.(e) Show how you could use ethyl (2-oxocyclohexane)carboxylate to prepare 2-methylcyclohexanone.(f) Give the structure of the product formed on treatment of ethyl (2-oxocyclohexane)-carboxylate with acrolein (H2C=CHCH=O) in ethanol in the presence of sodium ethoxidearrow_forwardPropanal and propanone react in a similar way with acidified aqueous potassium cyanide, KCN. For this reaction to occur reasonably quickly, the pH of the solution should be approximately 4. The reaction of propanal proceeds with acidified potassium cyanide proceeds more rapidly than that of propanone. Referring to the mechanism of the reactions, explain this phenomenon.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning