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 CHEM. VOL.1+2-W/WILEYPLUS
- (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_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_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_forwardWrite the structure for the major product of the following reaction.arrow_forwardThe odor of ripe bananas and many other fruits is due to the presence of esters. For example: Banana oil (isopentyl acetate) (a) Write the name (common or IUPAC) of the ester responsible for the fragrance of the following: pineapple, orange, apple, peach, & lavender (b) Choose one fragrant from (a) and name the alcohol and the carboxylic acid needed to synthesize this ester. (c) Show the detailed mechanism of the Fischer Esterification reaction that will be involved in the synthesis of the fragrant you have chosen in part (a).arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning