Concept explainers
(a)
Interpretation: The stereogenic center at
Concept introduction: The stereochemistry of the compound is determined by prioritizing the groups attached to its stereogenic center. The groups are prioritized on the basis of
(b)
Interpretation: The two isomeric products formed on reaction of A with
Concept introduction: Zincborohydride is a metal hydride reagent. It is a mild reducing agent which reduces
(c)
Interpretation: The reagent used to convert the A to the single stereoisomer X is to be predicted.
Concept introduction: The chiral oxazaborolidine catalysts are enantiomeric selective reducing reagent. The carbonyl group of ketones are reduced to form one stereoisomer in the enantiomeric excess.
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Organic Chemistry
- Kk.161.arrow_forwardShow how HC≡CH, CH3CH2Br, and (CH3)2CHCH2CH2Br can be used to prepare CH3CH2C≡CCH2CH2CH(CH3)2. Show all reagents, and use curved arrows to show movement of electron pairs.arrow_forward2. Draw ALL possible structural and stereochemical (if applicable) isomers. Please include enols (if oxygen is present) and enamines (if nitrogen is present), and any E and Z isomers in this analysis. a. C₂H4O b. a. C₂H₂O C. b. C4H₂O C₂H₂Narrow_forward
- f) Alkene X can be decomposed with hydrogen peroxide catalyzed by sodium tungstate to substance Q. This can be further degraded by iodoform reaction to substance R. Give the structures of substances Q and R. Xx S Na₂WO4 H₂O2 Q (C9H1603) 1: NaOH, 1₂ 2: H+ P₂O5 teplo - CHI3 R (C8H1404) P₂O5 teplo T g) The preparation of substance Q from substance X using hydrogen peroxide is a redox reaction. Identify the reductant and oxidant in this reaction, write the formal oxidation number to the atoms where it changes during the reaction and calculate the reaction. h) Substances Q and R undergo a reaction with phosphorous oxide under heating to form various products T and S. Determine the structure of substances T and S if you know their H NMR : 1H NMR (S): 2.2 (t, 2H); 1.8 (t, 2H); 1.3 (s, 6H). 1H NMR (T): 4.6 (d, 1H); 4.3 (d, 1H); 2.2 (t, 2H); 1.5 (t, 2H); 1.3 (s, 6H).arrow_forwardThe following scheme shows two reactions starting from alkene X. Hydroboration-oxidation of X gives the product as a racemic mixture of enantiomers. Based on the information below, determine the structure of compound A. Compound A is a racemic mixture of enantiomers. Draw only one enantiomer, using wedged and dashed bonds where appropriate. Do not provide compound X. n 6 1. BH3 Br2 A 2. H2O2, NaOH H2O OH plus enantiomer Create OscerSketch Answer 6arrow_forwardG.152.arrow_forward
- B. Describe the stereochemistry (with structures) of the addition of Br2 and H₂O to cyclohexene. C. Arrange the following ions by increasing basicity, where 1 is the most basic and 5 is the least. HCEC CH3CH3NH2 CH3CH₂O CH3CH₂ H₂C=CHarrow_forwardDraw one of the two enantiomers of the major product from this reaction. Use a dash or wedge bond to indicate stereochemistry of substituents on asymmetric centers. Ignore inorganic byproducts. so 1. B₂H6, THF 2. H₂O2, NaOH Select to Draw aarrow_forwardplease Includ rxn coordinate diagramarrow_forward
- See attached imagearrow_forwardCompound W, C6H13Cl, undergoes base-promoted E2 elimination to give a single C6H₁2 alkene, Y. Compound X, C6H13Br, undergoes a similar reaction to form Y and an isomeric alkene Z. W is chiral; X is not. Catalytic hydrogenation of Y and Z produces 2-methylpentane. Propose structures for W and X. 0 • Do not use stereobonds in your answer. • In cases where there is more than one possible structure for each molecule, just give one for each. Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate structures with + signs from the drop-down menu. -8) ChemDoodleⓇ Sn [Farrow_forwardDraw the structure resulting from a reaction of: 1. diborane (B₂H6), followed by 2. alkaline hydrogen peroxide (NaOH / H₂O2) with the following alkene. . Use the wedge/hash bond tools to indicate stereochemistry where it exists. . If a group is achiral, do not use wedged or hashed bonds on it. • If the reaction produces a racemic mixture, just draw one stereoisomer.arrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage LearningOrganic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning