(a)
Interpretation:
The synthesis of propranolol has to be shown from 1-naphthol.
(b)
Interpretation:
The chirality of Propranolol is to be identified and the possible stereoisomers has to be identified in the given synthesis.
Concept introduction:
Chiral:
A molecule is non superimposable on its mirror image is called chiral molecule.
Four different atoms attached to a carbon atom is called chiral molecule.
Isomer:
A molecule having the same molecular formula but with different chemical structure is called isomer.
Stereoisomers:
Stereoisomers are molecules that have the same molecular formula and they differ only in arrangement of atom in three-dimensional space.
Enantiomers:
A compound which is non-superimposable mirror image is called enantiomers.
Diastereomers:
A compound which is non-superimposable and non-mirror image is called diastereomers.
Racemic mixture:
A racemic mixture is simply a mixture containing an equal amount of each enantiomer.
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Chapter 21 Solutions
Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition
- Treatment of pentanedioic (glutaric) anhydride with ammonia at elevated temperature leads to a compound of molecular formula C5H7NO2. What is the structure of this product? [Hint: You need to think about the reactivity not only of acid anhydrides but also of amides and carboxylic acids]arrow_forwardList the structural features common to each of these molecules.arrow_forwardEarly organic chemists used the Hofmann elimination reaction as the last step of a process known as a Hofmann degradation—a method used to identify amines. In a Hofmann degradation, an amine is methylated with excess methyl iodide in a basic solution, treated with silver oxide to convert the quaternary ammonium iodide to a quaternary ammonium hydroxide, and then heated to allow it to undergo a Hofmann elimination. Once the alkene product is identified, working backward gives the structure of the amine. Identify the amine in each of the following cases: a. 4-Methyl-2-pentene is obtained from the Hofmann degradation of a primary amine. b. 3-Methyl-1-butene is obtained from the Hofmann degradation of a primary amine. c. 2-Methyl-1-3-butadiene is obtained from two successive Hofmann degradations of a secondary amine.arrow_forward
- Benzo(a)pyrene is a well known carcinogen. Based on its chemical properties, explain why benzo(a)pyrene and similar compounds are dangerous mutagens.arrow_forwardThe following substances can be prepared by a nucleophilic addition reaction between an aldehyde or ketoneand a nucleophile. Identify the reactants from which they were prepared. If the substance is an acetal, identifythe carbonyl compound and the alcohol; if it is an imine or enamine, identify the carbonyl compound and theamine. You do not have to consider stereochemistry. In cases where there is more than one answer, just giveone. Use Grignard reagents when an organometallic reagent is required. Draw the Grignard reagent as acovalent magnesium bromide.arrow_forward1) Nitriles are typically hydrolyzed to form what class of compounds? 2) what must one keep in mind when performing the hydrolysis of a nitrile to a carboxylic acid? 3) why are nitriles over-looked as carboxylic acid derivatives?arrow_forward
- helparrow_forwardProvide the systematic name for each of the following isomeric amides with the chemical formula C6H₁1 NO. (Be sure to indicate double bond stereochemistry using (E)/(Z) notation. Indicate stereochemistry in rings with the terms cis or trans. It is not necessary to use italics in writing compound names.) ball & stick + labels N-methylpent-4-enamide An error has been detected in your answer. Check for typos, miscalculations etc. before submitting your answer. ball & stick - + labels N, 3-dimethylbut-3-enamide ball & stick + labels (2Z)-2-methylpent-2-enamidearrow_forwardWhen the three benzaldehydes shown below were exposed to HCN under identical conditions it was found that the equilibrium constants, K, for the three cyanohydrin formation reactions were different. Based on principles that govern equilibrium processes for reversible carbonyl addition reactions, place the K values for the three reactions in ascending order (smallest to largest). Briefly justify your answer. (Hint: Recall that electron deficient carbonyls tend to react faster with nucleophiles and have larger equilibrium constants for the addition reaction.) H X O + HCN pH ~ 9-10 X = H, NO₂, OCH 3 OH H+CN Xarrow_forward
- The question is: "Draw the curved arrow mechanism for the reaction between pentan-2-one and (CH3)3O– in t-butanol to form an enolate. Draw all electrons and charges on both resonance structures. Then answer the question about the reaction." I got the initial arrows correct, but am not entirely sure what the carbanion intermediate would look like and then what the curved arrows would be to convert it to its final oxanion formarrow_forwardnoradrenaline and serotonin in the spinal cord. Deduce the structure of this new compound, given its molecular neuron to another. Noradrenaline (also called norepinephrine) and serotonin are neurotransmitters that act in its) Neurotransmitters are small molecules that are produced by the body to send messages from one the central nervous system. A recently report synthetic compound has effects that are similar to baul formula (CəH13NO) and the following 'H NMR spectral data. Show your work by labeling your proposed structure with the corresponding letters for the signals listed below. a) 1.1 6 (2H, broad singlet) b) 2.7 6 (2H, triplet) c) 2.9 6 (2H, triplet) d) 3.8 6 (3H, singlet) e) 6.8 6 (2H, doublet) f) 7.1 6 (2H, doublet)arrow_forwardPlease don't provide handwritten solutionarrow_forward
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