27. Which compound is NOT an i er of the oher three compounds (A) CH CHOH OH OH HO H. HO HO- H OH CH,OH (C) CH,OH (D) CH,OH он H- H OH HO HO H- HO- H. O- он CH,OH CH,OH
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- Explain the following result. Acetic acid (CH3COOH), labeled at its OH oxygen with theuncommon 18O isotope (shown in red), was treated with aqueous base, and then the solution was acidified. Two products having the 18O label at different locations were formed.Explain the following result. Acetic acid (CH3COOH), labeled at its OH oxygen with theuncommon 18O isotope (shown in red), was treated with aqueous base, and then the solution was acidied. Two products having the 18O label at different locations were formed.Explain this result: Acetic acid (CH3COOH), labeled at its OH oxygen with the uncommon 18O isotope (shown in red), was treated with aqueous base, and then the solution was acidified. Two products having the 18O label at different locations were formed.
- A key step in the synthesis of the narcotic analgesic meperidine (tradename Demerol) is the conversion of phenylacetonitrile to X. (a) What isthe structure of X? (b) What reactions convert X to meperidine ?the beginninf part is a benzene conntected to a O-H .Draw all of the substitution and elimination products formed from thegiven alkyl halide with each reagent: (a) CH3OH; (b) KOH. Indicate thestereochemistry around the stereogenic centers present in the products,as well as the mechanism by which each product is formed.
- Treatment of compound A (C8H17Br) with NaOCH2CH3 affords two constitutional isomers B and C. Ozonolysis of B affords CH2=O and (CH3CH2CH2)2C=O. Ozonolysis of C affords CH3CH2CH2COCH3 and CH3CH2CHO. What is the structure of A?32. Which of the following is INCORRECT? A. CH3COOH H+ + CH3COO- B. HF H+ + F- C. H2O H+ + O2- D. C2HO4- H+ + C2O42-The treatment of isoprene [CH2=C(CH3)CH=CH2] with one equivalent ofmCPBA forms A as the major product. A gives a molecular ion at 84 in itsmass spectrum, and peaks at 2850–3150 cm−1 in its IR spectrum. The 1HNMR spectrum of A is given below. What is the structure of A?
- Draw the products formed when both cis- and trans-but-2-ene are treated with a peroxyacid followed by -OH (in H2O).Explain how these reactions illustrate that anti dihydroxylation is stereospecic.The bicyclic heterocycles quinoline and indole undergo electrophilic aromatic substitution to give the products shown.(a) Explain why electrophilic substitution occurs on the ring without theN atom for quinoline, but occurs on the ring with the N atom in indole. (b)Explain why electrophilic substitution occurs more readily at C8 than C7in quinoline. (c) Explain why electrophilic substitution occurs morereadily at C3 rather than C2 of indole.The shrub ma huang (Section 5.4A) contains two biologically activestereoisomers—ephedrine and pseudoephedrine—with two stereogeniccenters as shown in the given structure. Ephedrine is one component ofa once-popular combination drug used by body builders to increaseenergy and alertness, whereas pseudoephedrine is a nasaldecongestant.a.) Draw the structure of naturally occurring (−)-ephedrine, which has the1R,2S configuration.b.) Draw the structure of naturally occurring (+)-pseudoephedrine, whichhas the 1S,2S configuration.c.) How are ephedrine and pseudoephedrine related?d.) Draw all other stereoisomers of (−)-ephedrine and (+) pseudoephedrine, and give the R,S designation for all stereogeniccenters.e.) How is each compound drawn in part (d) related to (−)-ephedrine?