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(a)
Interpretation: The number of stereogenic centers present in the product is to be determined.
Concept introduction: A carbon atom which is bonded to four different groups is termed as chiral center or stereogenic center. The groups around the stereogenic center are prioritized on the basis of
(b)
Interpretation: The product formed from the given reaction exhibit optical activity or not is to be predicted and explained.
Concept introduction: The replacement or substitution of one
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Chapter 18 Solutions
ORGANIC CHEMISTRY
- 5. What reagents are needed to convert toluene (C,H,CH,) to each compound? a. C.H.COOH b. C.H₂CH₂Br c. p-bromotoluene d. o-nitrotoluene e. p-ethyltoluene f.arrow_forwardDraw the structures of the products obtained from the reaction of each enantiomer of cis-1-chloro-2-isopropylcyclopentane with sodium methoxide in methanol. b. Are all the products optically active? c. How would the products differ if the starting material were the trans isomer? Are these products optically active? d. Will the cis enantiomers or the trans enantiomers form substitution products more rapidly? e. Will the cis enantiomers or the trans enantiomers form elimination products more rapidly?arrow_forwardselect reagents: cyclopentanone Reagents a. C6H5CHO b. NaOH, ethanol c. Pyrrolidine, cat. Hj. d. H₂C=CHCN e. H3O+ f. LDA g. A) bg EtOC(=O)CO₂Et h. i. B) ka k. I. m. O: BrCH₂CH=CH₂ NatOEt, ethanol Br₂, H+ K+ t-BUO™ CH2(CO2Et)z heat C) jh CO₂Et D) Imarrow_forward
- 6. What is the product of the following reaction? .CI L2Pd CH:-B NaOHarrow_forward2. Consijder the reactiojn scheme below a. Draw the major product of this reaction. Show clearly (using wedge-and-dash lines) all stereoisomers formed under these reaction conditions. 1. BH3:THF 2. H2O2, NaOH b. What is the stereochemical relationship between the different stereoisomer products you drew in part 2a.?arrow_forwardThese reagents can produce ketones with alkynes A. BH3, THF, H2O2 B. KMnO4 C. O3 D. H2SO4, H2O, HgSO4arrow_forward
- Rank the compounds according to their increasing reactivity toward electrophilic substitution. 1. Benzaldehyde 2. o-dimethylbenzene 3. nitrobenzene 4. phenolarrow_forwardcis-4-Bromocyclohexanol and trans-4-bromocyclohexanol form the same elimination product but a different substitution product when they reactwith HO-. a. Why do they form the same elimination product?b. Explain, by showing the mechanisms, why different substitution products are obtained.c. How many stereoisomers does each of the elimination and substitution reactions form?arrow_forwardSelect all compounds capable of keto-enol tautomerism. он H.C. он H.C. H.C. H.C. CH, CH, CH, H.C H.C a b darrow_forward
- Substitution and Elimination (Please draw the structures involved in the reactions) A. Which will react more rapidly via SN1? 1-bromo-2,2-dimethylpropane or 2-bromo-2- methylbutane? Explain. B. Which will react faster via SN2? 1-chlorocyclohexane or 1-chloro-1-methylcyclohexane? Explain.arrow_forwardWhich stereoisomer would be produced from the reaction of trans-2-butene with OsO4 followed by H2O2? A. 2S,3S- diol and 2R, 3R-diol B. 2S,3R-diol and 2R,3S-diol C. 2S,3S-diol only D. 2R, 3R-diol only E. 2S,3R-diol onlyarrow_forward4. The products created when 2-methylbut-2-ene reacts with one equivalence of hydrogen chloride arearrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
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