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) Give the products of the phosphoric acid-catalyzed dehydration of 2-methylcyclohex-3- enol. Label the three products with major, minor, and trace amounts. OH H3PO4, heat (b) Describe the rule that is applied in the acid-catalyzed dehydration of 2-methylcyclohex-3- enol. Explain your answer based on the products formed.arrow_forward(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_forward(a) Tsomane and Nyiko were given a task of synthesising methylenecyclohexane 2. After a brief discussion with each other, Tsomane proposed Method A to synthesise 2 from cyclohexanone 1 while Nyiko proposed Method B that started from hydroxymethylcyclohexane 3. Each student believed that their proposed method is better than the other. (Scheme below) (1) 1 Ph THF A Ph Ph B H₂SO4 100 °C 3 OH What is the name of the reaction that is followed by reaction Method A?arrow_forward
- Provide reagentsarrow_forwardComplete the following proposed acid–base reactions, and predict whether the reactants or products are favored.arrow_forwardConsider 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_forward
- When 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_forward17arrow_forwardApply retrosynthetic analysis to guide the preparation of each of the following compounds from the indicated starting material, then write out the synthesis showing the necessary reagents. (a) 1-Propanol from 2-propanol (b) 1,2-Dibromopropane from 2-bromopropane (c) 1-Bromo-2-propanol from 2-propanol (d) 1-Bromo-2-methyl-2-propanol from tert-butyl bromide (e) 1,2-Epoxypropane from 2-propanol (f) tert-Butyl alcohol from isobutyl alcohol (g) tert-Butyl iodide from isobutyl iodide (h) trans-2-Chlorocyclohexanol from cyclohexyl chloridearrow_forward
- (a) Tsomane and Nyiko were given a task of synthesising methylenecyclohexane 2. After a brief discussion with each other, Tsomane proposed Method A to synthesise 2 from cyclohexanone 1 while Nyiko proposed Method B that started from hydroxymethylcyclohexane 3. Each student believed that their proposed method is better than the other. (Scheme below) (1) Ph Ph 8*8 Ph THF A 1 Santande B H₂SO4 100 °C 3 OH Using curly arrows, provide full mechanistic details accounting how methylenecyclohexane 2 was synthesised according to both Methods A and B.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_forward(a) How will you convert:(i) Benzene to acetophenone (ii) Propanone to 2-Methylpropan-2-ol(b) Give reasons :(i) Electrophilic substitution in benzoic acid takes place at meta position.(ii) Carboxylic acids are higher boiling liquids than aldehydes, ketones and alcohols of comparable molecular masses.(iii) Propanal is more reactive than propanone in nucleophilic addition reactions.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning