Concept explainers
(a)
Interpretation:
For the given nitration reaction, orientation of the reaction has to be accounted.
Concept Introduction:
Activating and deactivating groups:
The effect of substituents on the reaction rate of
Activating groups – ortho/para directing groups. The
Deactivating groups – meta directing groups. The rate of reaction is decreased by a deactivating groups (electron withdrawing groups) relative to hydrogen.
(b)
Interpretation:
For the given substitution reaction in step 2, reaction mechanism has to be proposed.
Concept Introduction:
Activating and deactivating groups:
The effect of substituents on the reaction rate of aromatic electrophilic substitution is given by activating or deactivating groups.
Activating groups – ortho/para directing groups. The rate of reaction is increased by an activating groups (electron donating groups) relative to hydrogen.
Deactivating groups – meta directing groups. The rate of reaction is decreased by a deactivating groups (electron withdrawing groups) relative to hydrogen.
Trending nowThis is a popular solution!
Chapter 22 Solutions
Organic Chemistry
- Acid-catalyzed hydrolysis of the following epoxide gives a trans diol. Of the two possible trans diols, only one is formed. How do you account for this stereoselectivity?arrow_forwardExplain how benzaldehyde and dimedone reacts with each other, and then with the aminotriazole to form compound 1a in the presence of an acid catalyst. Provide a detailed reaction mechanism and explanation.arrow_forwardTranexamic acid, a drug useful against blood clotting, is prepared commercially from p-methylbenzonitrile. Following is one of the steps in its synthesis, draw the structure of the product of this step.arrow_forward
- The following compound undergoes Benzilic Acid Rearrangementto yield a hydroxyacid salt. Propose a mechanism for the reaction, write the major product, and provide an explanation as to the preference of migration of one R group over the other.arrow_forwardStearolic acid, C18H32O2, yields stearic acid on catalytic hydrogenation and undergoes oxidative cleavage with ozone to yield nonanoic acid and nonanedioic acid. What is the structure of stearolic acid?arrow_forwardThe last step in the synthesis of β-vetivone, a major constituent of vetiver, a perennial grass found in tropical and subtropical regions of the world, involves treatment of C with CH3Li to form an intermediate X, which forms β-vetivone with aqueous acid. Identify the structure of X and draw a mechanism for converting X to β-vetivone.arrow_forward
- Propose a synthesis of molecule B from molecule A. For each step, indicate the necessary reagents.arrow_forwardPropose a detailed mechanism for the transformations presented. represent the Intermediate structure A.arrow_forward(a) Explain the mechanism of a nucleophilic attack on the carbonyl group of an aldehyde or a ketone.(b) An organic compound (A) (molecular formula CgH16Q2) was hydrolysed with dilute sulphuric acid to give a carboxylic acid (B) and an alcohol (C). Oxidation of (C) with chromic acid also produced (B). On dehydration (C) gives but-1-ene. Write the equations for the reactions involved.arrow_forward
- Two isomers, A and B, of molecular formula C5H8 undergo catalytic hydrogenation with hydrogen gas and palladium on carbon to form the same C5H10 product. On ozonolysis followed by treatment with hydrogen peroxide (H2O2), isomer A gave a product of molecular formula C5H8O4 that has two carboxylic acid groups in it whereas isomer B gave a product of molecular formula C5H8O3 that contains a carboxylic acid group and a ketone group. Which of the following isomeric pairs best match this data?arrow_forwardTwo isomers, A and B, of molecular formula C5H8 undergo catalytic hydrogenation with hydrogen gas and palladium on carbon to form the same C5H10 product. On ozonolysis followed by treatment with hydrogen peroxide (H2O2), isomer A gave a product of molecular formula C5H8O4 that has two carboxylic acid groups in it whereas isomer B gave a product of molecular formula C5H8O3 that contains a carboxylic acid group and a ketone group. What is the isometric pair of A and B that corresponds?arrow_forwardplease help with this question. thank you. The following sequence, beginning with a cyclic hemiacetal (compound A), was part of a recently reported enantiospecific synthesis of a powerful sex pheromone (currently used in pest management) of the mealybug Pseudococcus viburni: Draw the structures of compound B and C. Provide a plausible mechanism to explain the transformation from compound C into compound D. Identify the reagents you would need to convert compound D into compound F (in just two steps). Also identify the structure of compound E.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning