Concept explainers
(a)
Interpretation: The stereogenic center(s) is to be labeled.
Concept introduction: Stereoisomers are the compounds in which molecular formula of a compound remains same but positions of different atoms or groups are changed to form new compounds. The stereogenic centers are also known as sterocenters. The stereocenters are carbon atoms on which the interchanging of two atoms or groups results in the formation of new stereoisomers.
(b)
Interpretation: Amide(s) that can be reduced to form benzphetamine is to be predicted.
Concept introduction:
(c)
Interpretation: The carbonyl compound and amine that can be used to make benzphetamine by reductive amination are to be stated. The possible methods are to be drawn.
Concept introduction: Amines are the derivatives of ammonia consisting of nitrogen atom with the lone pair of electrons. They are basic compounds. The synthesis of the products relies upon the type of reactants and reagents that are used during the reactions. The energy of a target molecule should be low because it increases the stability of a molecule that results in the formation of molecules with high yield. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.
(d)
Interpretation: The products which are formed by Hofmann elimination from benzphetamine are to be drawn. The major product is to be labeled.
Concept introduction: Amines are the derivatives of ammonia consisting of nitrogen atom with the lone pair of electrons. They are basic compounds. Hoffman’s elimination reaction involves the less substituted alkene as a more favourable product, whereas according to Zaitsev rule, more substituted
Trending nowThis is a popular solution!
Chapter 25 Solutions
Organic Chemistry
- Etoposide, sold as a phosphate derivative with the trade name ofEtopophos, is used for the treatment of lung cancer, testicular cancer,and lymphomas. What products are formed when all of the acetals are hydrolyzed with aqueous acid?arrow_forwardIn the 1880's, Acetanilide, sold under the name Antifebrin, was widely used as a pain reliever and fever reducer. However, it had many adverse side effects, including cyanosis as a result of methemoglobinemia. The toxic side effects were the result of a small portion of acetanilide being hydrolyzed to aniline. Acetanilide was discontinued and replaced with phenacetin. Later studies show that both acetanilide and phenacetin are metabolized to acetaminophen. This metabolite, which we know as Tylenol, is responsible for the analgesic and antipyretic properties. Part 1: Show a detailed arrow pushing mechanism of the acid catalyzed hydrolysis of acetanilide to aniline Part 2: Propose a synthesis of Acetaminophen from phenol NH NH NH Phenacetin inophen Acetanilide Attach File Browse Local Files Browse Content Collectionarrow_forwardRank the nitrogen atoms in each compound in order of increasing basicity. Isoniazid is a drug used to treat tuberculosis, whereas histamine (Section 25.6B) causes the runny nose and watery eyes associated with allergies.arrow_forward
- (a) Draw the structure of the hemiacetal formed from one mole of benzaldehyde and one mole of ethanol. (b) Draw the structure of the acetal formed from one mole of benzaldehyde and two moles of ethanol. (c) Draw the structure of 2-methoxy-2-butanol. What compounds could you prepare this from? (d) Draw the structure of 3-methoxyl-2-butanol. What functional groups are present? Is this an acetal, a hemiacetal, or neither? Explain. (e) Identify the functional groups in the molecules shown below. Circle any acetals or hemiacetal, and identify which they are. 0-arrow_forwardWith reference to the structures of acetylsalicylic acid (aspirin) and acetaminophen (the active ingredient in Tylenol), explain why acetaminophen tablets can be stored in the medicine cabinet for years, but aspirin tablets slowly decompose over time.arrow_forward(a) Explain why phentermine [PhCH2C(CH3)2NH2] can’t be made by a reductive amination reaction.(b) Give a systematic name for phentermine, one of the components of the banned diet drug fen–phen.arrow_forward
- Draw the products formed when attached carbonyl compound reacts with the following amines: [1] CH3CH2CH2NH2; [2] (CH3CH2)2NH.arrow_forward(a) Label the acetal in salicin, a naturally occurring pain reliever isolated from the bark of the willow tree. (b) How many 1° OH groups does salicin contain?arrow_forwardMethylparaben is a common preservative used in cosmetics. What carboxylic acid and alcohol are needed to synthesize methylparaben by Fischer esterifi cation?arrow_forward
- Answer the following questions about benzphetamine, a habit-forming diet pill sold under the trade name Didrex. a. Label the stereogenic center(s). b. What amide(s) can be reduced to form benzphetamine? c. What carbonyl compound and amine can be used to make benzphetamine by reductive amination? Draw all possible methods. d. What products are formed by Hofmann elimination from benzphetamine? Label the major product. benzphetaminearrow_forward(a) Draw the structure of the hemiacetal formed from one mole of benzaldehyde and one mole of ethanol. (b) Draw the structure of the acetal formed from one mole of benzaldehyde and two moles of ethanol. (c) Draw the structure of 2-methoxy-2-butanol. What compounds could you prepare this from?arrow_forwardEthyl butyrate, CH3CH2CH2CO2CH2CH3CH3CH2CH2CO2CH2CH3, is an artificial fruit flavor commonly used in the food industry for such flavors as orange and pineapple. Its fragrance and taste are often associated with fresh orange juice, and thus it is most commonly used as orange flavoring. It can be produced by the reaction of butanoic acid with ethanol in the presence of an acid catalyst (H+H+): CH3CH2CH2CO2H(l)+CH2CH3OH(l)H+⟶CH3CH2CH2CO2CH2CH3(l)+H2O(l)CH3CH2CH2CO2H(l)+CH2CH3OH(l)⟶H+CH3CH2CH2CO2CH2CH3(l)+H2O(l) A chemist ran the reaction and obtained 5.40 g of ethyl butyrate. What was the percent yield, The chemist discovers a more efficient catalyst that can produce ethyl butyrate with a 78.0% yield. How many grams would be produced from 7.45g of butanoic acid and excess ethanol?arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningChemistry for Today: General, Organic, and Bioche...ChemistryISBN:9781305960060Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. HansenPublisher:Cengage Learning
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning