Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 9.SE, Problem 49AP
Occasionally, a chemist might need to invert the stereochemistry of an
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Consider a reaction where cis-but-2-ene is treated with a peroxy acid followed by OH- /H20. Draw the structure of one product that is formed in the reaction, including correct stereochemistry.
Draw the structure for an alkene that gives the following reaction product.
1. Hg(OАc)2, Н2О
?
-CHCH3
2. NABH4
ОН
Ignore alkene stereochemistry.
You do not have to explicitly draw H atoms.
In cases where there is more than one answer, just draw one.
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opy aste
ChemDoodle
Draw the alkene that would react with the reagent given to account for the product formed.
? +
+
H₂O
****
H₂S04
• 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.
CH3
CH3 CHCCH3
| |
OH CH3
+1
Chapter 9 Solutions
Organic Chemistry
Ch. 9.1 - Prob. 1PCh. 9.1 - Prob. 2PCh. 9.3 - What products would you expect from the following...Ch. 9.4 - Prob. 4PCh. 9.4 - Prob. 5PCh. 9.4 - Prob. 6PCh. 9.4 - Prob. 7PCh. 9.5 - Using any alkyne needed, how would you prepare the...Ch. 9.7 - The pKa of acetone, CH3COCH3, is 19.3. Which of...Ch. 9.8 - Prob. 10P
Ch. 9.8 - Prob. 11PCh. 9.9 - Show the terminal alkyne and alkyl halide from...Ch. 9.9 - Beginning with acetylene and any alkyl halide...Ch. 9.SE - Name the following alkynes, and predict the...Ch. 9.SE - From what alkyne might each of the following...Ch. 9.SE - Prob. 16VCCh. 9.SE - The following cycloalkyne is too unstable to...Ch. 9.SE - Prob. 18MPCh. 9.SE - Assuming that strong acids add to alkynes in the...Ch. 9.SE - Prob. 20MPCh. 9.SE - Prob. 21MPCh. 9.SE - Prob. 22MPCh. 9.SE - Prob. 23MPCh. 9.SE - Prob. 24MPCh. 9.SE - Reaction of acetone with D3O+ yields...Ch. 9.SE - Give IUPAC names for the following compounds:Ch. 9.SE - Draw structures corresponding to the following...Ch. 9.SE - Prob. 28APCh. 9.SE - Prob. 29APCh. 9.SE - Prob. 30APCh. 9.SE - Predict the products from reaction of l-hexyne...Ch. 9.SE - Prob. 32APCh. 9.SE - Prob. 33APCh. 9.SE - Propose structures for hydrocarbons that give the...Ch. 9.SE - Identify the reagents a-c in the following scheme:Ch. 9.SE - Prob. 36APCh. 9.SE - Prob. 37APCh. 9.SE - Prob. 38APCh. 9.SE - How would you carry out the following...Ch. 9.SE - Prob. 40APCh. 9.SE - Synthesize the following compounds using 1-butyne...Ch. 9.SE - Prob. 42APCh. 9.SE - Prob. 43APCh. 9.SE - Prob. 44APCh. 9.SE - Prob. 45APCh. 9.SE - A hydrocarbon of unknown structure has the formula...Ch. 9.SE - Compound A(C9H12) absorbed 3 equivalents of H2 on...Ch. 9.SE - Hydrocarbon A has the formula C12H8. It absorbs 8...Ch. 9.SE - Occasionally, a chemist might need to invert the...Ch. 9.SE - Prob. 50APCh. 9.SE - Prob. 51APCh. 9.SE - Prob. 52APCh. 9.SE - Prob. 53APCh. 9.SE - Prob. 54APCh. 9.SE - Prob. 55APCh. 9.SE - Prob. 56APCh. 9.SE - Prob. 57AP
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- 4. What are the products obtained from the following elimination reaction? Indicate the major product. CH3 CH,CH,ČCH, H2O 5. a) Determine the major product that is formed when the alkyl halide reacts with a hydroxide ion in an elimination reaction. CH;CH,CH,CH,CCH, Br b) For the major elimination product obtained in 5a), which stereoisomer (cis or trans) is obtained in greater yield? Draw the two isomers and provide the names of the compounds.arrow_forwardProvide detailed step-wise mechanism for the following reaction. Be sure to show all intermediates, formal charges, and show the movement of electrons with curved arrows. a 4+H₂Q 044 OHarrow_forwardDraw the alkene that would react with the reagent given to account for the product formed. ? + HCI My 3 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. CH3 CH₂ CHOCH3 TT CI CH3 L ▼ {n [F ? ChemDoodleⓇarrow_forward
- CH3 CH3 Br- Br2 .CH3 CH2Cl2 CH3 H3C H3C Br Electrophilic addition of bromine, Brɔ, to alkenes yields a 1,2-dibromoalkane. The reaction proceeds through a cyclic intermediate known as a bromonium ion. The reaction occurs in an anhydrous solvent such as CH,Cl,. In the second step of the reaction, bromide is the nucleophile and attacks at one of the carbons of the bromonium ion to yield the product. Due to steric clashes, the bromide ion always attacks the carbon from the opposite face of the bromonium ion so that a product with anti stereochemistry is formed. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions CH3 CH3 CH3 CH3 H3C H3C :Br: :Br:arrow_forwardDraw a structural formula for the major product of the reaction shown. H3C Cl2 H3C H20 Show product stereochemistry IF the reactant alkene has both carbons of the double bond within a ring. • Do not show stereochemistry in other cases. • If the reaction produces a racemic mixture, just draw one stereoisomer. opy aste - [F ChemDoodle Previous Nexarrow_forwardWhen treated with NaOH, the bromide below gives an alkene by the E2 mechanism, by eliminationof the circled atoms: (a) Draw the Newman projection from which elimination takes place. (b) Draw the mechanism. (c) Draw the product with the proper stereochemistry. (d) Assign the proper stereochemical descriptor to the product. (Z, E? Trans,CiS?) (e)What would happen to the stereochemistry of the product if the enantiomer of the starting material were used inthe reaction?arrow_forward
- Consider the following mechanism of reaction: CH3 CH, CH3 CH;C CH, + H-CI CH;CCH, + C: → CH;CCH, tert-butyl cation CI tert-butyl chloride In this reaction: The alkene and the carbocation intermediate are both nucleophilic HCl and CI" are both nucleophilic The alkene and HCI are both electrophilic The carbocation and CI" are both electrophilic The alkene and CI" are both nucleophilic AMeving to another question will save this responsearrow_forwardDraw the most stable resonance form for the intermediate in the following electrophilic substitution reaction. CH3 CH3 H3PO4 HO, + H3C CH3 HO HO First stage in synthesis of the epoxy and polycarbonate ingredient bisphenol-A You do not have to consider stereochemistry. Include all valence lone pairs in your answer. In cases where there is more than one answer, just draw one.arrow_forward9) Draw the conformer structure, Newman projection, before elimination and the elimination product of the following reaction: Br CH3ONA Harrow_forward
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