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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Chapter 29 Solutions
Connect Online Access 1-Semester for Organic Chemistry
- 2. 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_forwardf) 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_forward
- Draw the structure for an alkene that gives the following reaction product. 7 CH2l2, Zn/Cu Ignore alkene stereochemistry. • You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one. / [F ?arrow_forwardB. 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_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_forward
- Compound A, C₂H16 reacts with 1 molar equivalent(s) of hydrogen on catalytic hydrogenation. A undergoes reaction with ozone, followed by Zn treatment, to give: O CH3 O || CH3CCH₂CCH₂CCH3 CH3 Compound A Propose a structure for A. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one.arrow_forward10. A compound X of molecular formula C8H12 with no triple bonds reacts with one equivalent of H2 to give a new compound having molecular formula CaH14. What can be inferred about the structure of compound X? A) Compound X has 3 rings. B) Compound X has 3 pi bonds. Compound X has 1 ring and 2 pi bonds. D) Compound X has 2 rings and 1 pi bond. 11. Determine the product of the following reaction. H, Lindlar's cat. %3D IV A)I B) II C) III D) IV Type here to search 互i | A C 三Darrow_forwardCompound X, C,4H12Br2, is optically inactive. On treatment with strong base, X gives hydrocarbon Y, C14H10: Compound Y absorbs 2 equivalents of hydrogen when reduced over a palladium catalyst to give z (C14H14) and reacts with ozone to give one product, benzoic acid (C,Hg02). Draw the structure of compound Z. • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • Ignore alkene stereochemistry. • If more than one structure fits the description, draw them all. • 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. ChemDoodlearrow_forward
- b) Optical isomers can often be formed during these reactions. For products A-H indicate how many different optical isomers you expect to form for each from these reactions (you do not have to indicate whether they are diastereomers/enantiomers). c) In the preparation of substance D by ozonolysis, the second step is necessary treatment of the reaction mixture with zinc in acetic acid. If we forgot this step, we would get substance V instead of substance D, which would probably explode when isolated. What is the structure of substance V? *24 X 1: ozone V e) What products do you expect to form if they react with alkene X: I - HBr in diethyl ether; II - Brl in methanol; III - PhSCI in diethyl ether; IV - Selectfluor in methanol. P M EtOH NA EtONa PhSNa EtOH E H+ O TsCl Pyridín F- T2, Pd/C G4 mCPBA H₂SO4 10 %, H₂O 1: BH3 H◄ 2: H₂O₂ ill X Br₂ cyclohexane HCI A > В B HBr warmth, benzoylperoxid 1: ozone 2: Zn, ACOH Mg THF с D D₂O K I + J NaOHarrow_forwardDraw the major organic product formed by reaction of 2-hexyne with the following reagent: BH3 followed by CH3COOH. . Consider E/Z stereochemistry of alkenes. In cases where there is more than one answer, just draw one. • If no reaction occurs, draw the organic starting material.arrow_forwardExplain why the reaction of 2-bromopropane with NaOCOCH3 gives (CH3)2CHOCOCH3 exclusively as product, but the reaction of 2-bromopropane with NaOCH,CHg gives a mixture of (CH3)CHOCH,CHs (20%) and CH3CH=CH2 (80%).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
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