Concept explainers
17-54 Following is the structure of immunosuppressant FK-506, a molecule shown to disrupt calcineurin-mediated signal transduction in T-lymphocytes.
(a) There are three carbon—carbon double bonds present in this molecule. Which of the three has the potential for cis/trans isomerism? Assign a cis or trans con?guration to each carbon-carbon double bond that has this possibility.
(b) How many stereocenters are present in this molecule? How many stereoisomers are possible for it?
(c) Are there any aromatic components in this molecule?
(d) Consider the two carbon atoms marked with asterisks. Assign an R or S con?guration of each stereocenter.
(e) Because of the presence of a 21-member ring, this molecule is described as a macrocycle. This ring is fashioned by three types of bonds, several carbon-carbon bonds, one ester, one hemiacetal, and one amide. Locate the ester and the hemiacetal.
(f) Draw the structural formula of the long chain compound that would result if the hemiacetal were to be cleaved to an alcohol and a carbonyl group.
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Chapter 16 Solutions
Introduction To General, Organic, And Biochemistry
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- 10) 11)arrow_forwardThe amino acid serine is shown below. What functional groups are present in this molecule as drawn? O || H₂N-CH-C-OH I CH₂ I OH (A) ketone, carboxylic acid, amide (B) ester, alcohol, amine (C) carboxylic acid, amine, alcohol (D) ester, amide, alcoholarrow_forward[10] 10] Q1. Do the following conversions as directed. Write the complete reaction equation. (a) Benzaldehyde to Benzoic Acid. (b) Propanal to 1-propanal (c) Cyclohexanone to Cyclohexanol (d) Acetaldehyde to Ethyl alcohol (e) Acetone to Iso-propyl alcoholarrow_forward
- Each member of the following set of compounds is an amine; that is, each contains a nitrogen atom bonded to one, two, or three carbon groups (Section 10.4B). Which structural formulas represent the same compound, and which represent constitutional isomers? (a) (c) (e) NH₂ -on (g) (g) N|H Η 342 Chapter 11 Alkanes H-N Η (b) NH₂ (d) a NH NH₂ (f) - (h) N II H NH₂arrow_forwardIntramolecular H-bonding (IHB) are interactions that occur within one single molecule. IHB is also known as chelation, since it involves ring formation. Which of the following is (are) stabilized by IHB? * QH Çi OH -NO2 (a) Cl-Ç–Ç–H (b) či ÓH OH (с) CH, —С—СH—С—ОС,Н, CH,OH (d) | CH,OH D B Aarrow_forwardWhat is the relationship, if any, between these organic compounds?arrow_forward
- Are the pairs of compounds shown below the same molecule, isomers, or different molecules?arrow_forwardDraw structures that t each description and name the functional group in each molecule: (a) two constitutional isomers with molecular formula C5H10O that contain different functional groups; (b) two constitutional isomers with molecular formula C6H10O that contain the same functional group.arrow_forward1 12. Identify the set of compounds that have the same functional group. (a) C2H6, C2H4, C2H2 (b) C2H2, CH3COOH, CH3CONH2 (с) СНЗСН2CНО, Н2СО, СНЗСH2CH2CH2CНO (d) CH3NH2, CH3CH2CONH2, CH3CH2CONHCH3 (e) СНЗС(О)СНз, СНЗСООН, CH:CH2CHOarrow_forward
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