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
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Chapter 25 Solutions
ORGANIC CHEM.(LL)W/STD GDE.+CONNECT PKG
- What products are formed when all of the amide and ester bonds arehydrolyzed in each of the following compounds? Tamiflu [part (a)] is the trade name of the antiviral agent oseltamivir, thought to be the most effective agent in treating influenza. Aspartame [part (b)] is the artificial sweetener used in Equal and many diet beverages. One of the products of this hydrolysis reaction is the amino acid phenylalanine. Infants afflicted with phenylketonuria cannot metabolize this amino acid, so it accumulates, causing mental retardation. When the affliction is identified early, a diet limiting the consumption of phenylalanine (and compounds like aspartame that are converted to it) can make a normal life possible.arrow_forwardWhich hemiacetal would be formed under acidic conditions?arrow_forwardWhat products are formed when all of the amide and ester bonds are hydrolyzed in each of the following compounds? Tamiu [part (a)] is the trade name of the antiviral agent oseltamivir, thought to be the most effective agent in treating inuenza. Aspartame [part (b)] is the articial sweetener used in Equal and many diet beverages. One of the products ofthis hydrolysis reaction is the amino acid phenylalanine. Infants afflicted with phenylketonuria cannot metabolize this amino acid, so it accumulates, causing mental retardation. When the affliction is identied early, a diet limiting the consumption of phenylalanine (and compounds like aspartame that are converted to it) can make a normal life possible.arrow_forward
- Synthadotin is a promising anticancer drug in clinical trials. a.Identify the functional groups. b.Classify any amine or amide as 1°, 2°, or 3°. c.At which sites can synthadotin hydrogen bond to another molecule like itself? d. Label two nucleophilic sites. e. Label two electrophilic sites. f. What product is formed when synthadotin is treated with HCl?arrow_forwardAnswer the following questions about atomoxetine, a drug used to treatattention deficit hyperactivity disorder (ADHD). a.) What amides can be reduced to form atomoxetine?b.) What starting materials can be used to form atomoxetine by reductiveamination? Draw all possible methods.c.) What products are formed by Hofmann elimination of atomoxetine?arrow_forwardAlthough γ-butyrolactone is a biologically inactive compound, it is converted in the body to 4-hydroxybutanoic acid (GHB), an addictive and intoxicating recreational drug. Draw a stepwise mechanism for this conversion in the presence of acid.arrow_forward
- What products are formed when all of the amide and ester bonds are hydrolyzed in each of the following compounds? Tamiflu [part (a)] is the trade name of the antiviral agent oseltamivir, thought to be the most effective agent in treating influenza. Aspartame [part (b)] is the artificial sweetener used in Equal and many diet beverages. One of the products of this hydrolysis reaction is the amino acid phenylalanine. Infants afflicted with phenylketonuria cannot metabolize this amino acid, so it accumulates, causing mental retardation. When the affliction is identified early, a diet limiting the consumption of phenylalanine (and compounds like aspartame that are converted to it) can make a normal life possible.arrow_forwardRank the labeled N atoms in the anticancer drug imatinib (trade nameGleevec) in order of increasing basicity. Imatinib, sold as a salt withmethanesulfonic acid (CH3SO3H), is used for the treatment of chronicmyeloid leukemia as well as certain gastrointestinal tumors.arrow_forwardShow how to convert amines to other functional groups, and devise multistepsyntheses using amines as starting materials and intermediatesarrow_forward
- What is the major Hofmann elimination product formed from each amine?arrow_forwardQuinapril (trade name Accupril) is used to treat high blood pressure andcongestive heart failure. One step in the synthesis of quinapril involvesreaction of the racemic alkyl bromide A with a single enantiomer of theamino ester B. Given the structure of quinapril, which one of these two products isneeded to synthesize the drug?arrow_forwardWhat amide(s) can be used to prepare each amine by reduction?arrow_forward
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