(a)
Interpretation:
The resonance of
Concept introduction:
Spectroscopy method is used to identify the structure of the molecule. It is based on the interactions between matter and
(b)
Interpretation:
The amount of each anomer of
Concept introduction:
The anomers are cyclic monosaccharides, which differ in configuration at one stereogenic center. These carbon atoms are called the anomeric center. For example
Want to see the full answer?
Check out a sample textbook solutionChapter 24 Solutions
Organic Chemistry
- Determining if a Base Is Strong Enough to Deprotonate an Acid Which of the following bases is strong enough to deprotonate N,Ndimethylacetamide [CH3CON(CH3)2, pKa = 30], so that equilibrium favors the products:(a)NaNH2; (b) NaOH?arrow_forwardwhat is the structure of o-methylphenoxide anion and what is its pKa?arrow_forwardPQ-29. What is the major product of this reaction? (A) ОН (B) OH OH 1) excess CH3Li 2) H30+ (D) Нarrow_forward
- (a) How many Stereoisomers are possible for 9,10- dibromoexadecanoic acid?(b) Addition of bromine to palmitoleic acid primarily yields a set of enantiomers, (±) -three-9,10-dibromohexadecanoic acid. The addition of bromine is an anti-addition to the double bond (ie, it appears to occur through the intermediary of the bromonium ion). Taking into account the stereochemistry of the cis double bond of palmitoleic acid and the stereochemistry of adding bromine,Write a three-dimensional structure for (±) -three-9,10-dibromohexadecanoic acid!arrow_forwardWhich substituents have an electron-withdrawing and which have an electron-donating inductive effect: (a) CH3CH2CH2CH2−; (b) Br−; (c) CH3CH2O−?arrow_forwardAlthough codeine occurs in low concentration in the opium poppy, most of the codeine used in medicine is prepared from morphine (the principal component of opium) by the following reaction. Explain why selective methylation occurs at only one OH in morphine to give codeine. Codeine is a less potent and less addictive analgesic than morphine. но. CH,0. [1 кон H [2] CH3I H. CH3 H Ho morphine H. CH3 Ho codeinearrow_forward
- Acetic acid can also react as a very weak base (pKb = 20). Two different sites on acetic acid might become protonated to give the conjugate acid. Draw both of these possible conjugate acids, and explain (resonance) why the correct one is more stable. Calculate the pKa of this conjugate acid.arrow_forwardDraw the following compounds. a) (25,5Z)-2-amino-6-bromohept-5-enoic acid b) (S)-2,3-epoxy-4-hydroxycyclohexanonearrow_forwardPQ-20. This type of reaction, typical of carboxylic acids, esters, acid halides, anhydrides and amines, is called: (A) a bimolecular nucleophilic substitution. (C) an electrophilic substitution. (A) (A) H3C-C-OCH₂CH3 OH R CI PQ-21 What would be hydrolyzed most slowly with aqueous NaOH? lo (B) OH₂ (C) H3C-C-OCH₂CH3 H3C-C- H CI + H₂O (B) a nucleophilic addition. (D) a nucleophilic acyl substitution. (C) PQ-22. Which structure is a reasonable intermediate in the acid-catalyzed hydrolysis of ethyl acetate, shown, in dilute aqueous acid? RiOH OH (D) H3C- (D) OH (B) H3C-C-OCH₂CH3 OH₂ + HCI si inarrow_forward
- The addition of a nucleophilic group like a thiol (-SH), or an unprotonated amino group (-NH₂) to an a,ß-unsaturated ketone is important for understanding how NAPQI reacts with glutathione, N-acetylcysteine, or protein amino acid side chains containing -SH or -NH2 groups. In this problem we will add mercaptoethanol to p-benzoquinone. p-Benzoquinone will be a simple model of NAPQI. +H H a single uncharged addition product This reaction will proceed in steps. First the H-S-R will add to the unsaturated ketone to give a charged addition product. Next, a simple proton transfer will form an uncharged adduct in which the 6-membered ring contains one carbonyl and a second enolic hydroxyl. The keto form next will tautomerize to its more stable enol form, and in doing so the 6-membered ring becomes aromatic with 6-π electrons. See page 14 of the lecture notes for Lecture 9 How ADME affects preclinical Drug Design February 24, 2023, where I have shown the mechanism for this addition and give the…arrow_forwardLook up the structure of lisdexamfetamine (Vyvanse), a drug used in the treatment of attention deficit hyperactivity disorder (ADHD). Redraw it and identify all the functional groups present. What is known about itstherapeutic properties?arrow_forward(−)-Hyoscyamine, an optically active drug used to treat gastrointestinal disorders, is isolated from Atropa belladonna, the deadly nightshade plant, by a basic aqueous extraction procedure. If too much base is used during isolation, optically inactive material is isolated. (a) Explain this result by drawing a stepwise mechanism. (b) Explain why littorine, an isomerisolated from the tailower plant in Australia, can be obtained optically pure regardless of the amount of base used during isolation.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning