Concept explainers
(a)
Interpretation:
A mechanism has to be proposed for the formation of the protected
Concept introduction:
Hydrolysis is a chemical process in which a molecule is cleaved into two parts by the addition of a molecule of water. If the reaction is carried out with the help of an acid it is said to be an acid catalyzed hydrolysis.
Mechanism of the reaction is the step-by-step description of the process by which reactants are changed into products.
Curved arrows show the bonds that are formed and the bonds that are broken in a reaction.
Curved arrows used to understand a reaction mechanism.
Electrophile: It is positively charged species which seeks for negative charge and hence accepts pair of electrons from negatively charged species (Nucleophiles) which results in the formation of
Nucleophile: It is negatively charged species which seeks for positive charge and hence donate pair of electrons to positively charged species (electrophiles) which results in the formation of chemical bond.
(b)
Interpretation: An experimental procedure has to be suggested whereby the protecting group in the reaction can be removed to regenerate the unprotected diol.
Concept introduction:
Hydrolysis is a chemical process in which a molecule is cleaved into two parts by the addition of a molecule of water. If the reaction is carried out with the help of an acid it is said to be an acid catalyzed hydrolysis.
Mechanism of the reaction is the step-by-step description of the process by which reactants are changed into products.
Curved arrows show the bonds that are formed and the bonds that are broken in a reaction.
Curved arrows used to understand a reaction mechanism.
Electrophile: It is positively charged species which seeks for negative charge and hence accepts pair of electrons from negatively charged species (Nucleophiles) which results in the formation of chemical bond.
Nucleophile: It is negatively charged species which seeks for positive charge and hence donate pair of electrons to positively charged species (electrophiles) which results in the formation of chemical bond.
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Chapter 16 Solutions
Organic Chemistry
- A problem often encountered in the oxidation of primary alcohols to acids is that esters are sometimes produced as by-products. For example, oxidation of ethanol yields acetic acid and ethyl acetate: Propose a mechanism to account for the formation of ethyl acetate. Take into account the reversible reaction between aldehydes and alcohols:arrow_forwardProvide reagentsarrow_forwardA synthetic organic molecule, G, which contains both aldehyde and ether functional groups, is subjected to a series of reactions in a multi-step synthesis pathway. In the first step, G undergoes a Wittig reaction, leading to the formation of an alkene, H. Subsequently, H is treated with an ozone (O3) reagent followed by a reducing agent in an ozonolysis reaction, resulting in the formation of two different products, I and J. Considering the functional groups present in G and the nature of the reactions involved, what are the most probable structures or functional groups present in products I and J? A. I contains a carboxylic acid group, and J contains an aldehyde group. B. I contains a ketone group, and J contains an alcohol group. C. I and J both contain aldehyde groups. D. I contains an ester group, and J contains a ketone group. Don't use chat gpt.arrow_forward
- (c) Draw the structure of the hemi-acetal and acetal formed when cyclohexanone is combined with methanol in the presence of catalytic acid.arrow_forwardShow how you would synthesize octanal from each compound. You may use any necessary reagents.(a) octan-1-olarrow_forwardExplain the mechanism of the following reactions :(i) Addition of Grignard’s reagent to the carbonyl group of a compound forming an adduct followed by hydrolysis.(ii) Acid catalysed dehydration of an alcohol forming an alkene.(iii) Acid catalysed hydration of an alkene forming an alcohol.arrow_forward
- The 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_forwardCompound A has molecular formula C7H15B.. Treatment of compound A with sodium ethoxide yields only one elimination product (compound B) and no substitution products. When compound B is treated with dilute sulfuric acid, compound C is obtained, which has molecular formula C7H160. Draw the structures of compounds A, B, and C.arrow_forwardSuggest possible synthetic route for following transformations. Show the reagents, intermediates and products.arrow_forward
- Provide the reagents needed to bring about the following transformations.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_forwardShow how the following ketones might be synthesized from the indicated acids, usingany necessary reagents.(b) methyl cyclohexyl ketone from cyclohexanecarboxylic acidarrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning