Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 11.4, Problem 9P
Interpretation Introduction
Interpretation:
The percentage inversion and the percentage racemization occurred when pure tosylate -2,2-dimethyl-1-phenyl-1-propanol reacted with acetic acid is interpreted.
Concept introduction:
The SN1 reaction occurs through carbocation intermediate. The planar achiral carbocation intermediate gives the racemic product.
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
In the reaction of trans-cinnamaldehyde under the conditions of 2-propanol and gamma-Al2O3, the product yielded is cinnamyl alcohol.
When the reaction was first performed the GC and IR showed signals of the formation of a carbocation-like intermediate on the phenyl ring. The 2-propanol used contained high amounts of HCl. How does the high amount of HCl in 2-propanol affect gamma-Al2O? Also, show the intermediate that was formed?
The second reaction performed did not contain high amounts of HCl so the product formed was cinnamyl alcohol. Draw the proton NMR spectrum of cinnamyl alcohol.
Which of the structures A through D is an intermediate in the synthesis of N-methyl phthalimide (2) from phthalic anhydride (1)? Click on a letter A through D to answer.
HC-NH2
N-CH3
2 0
N-CH
CHO.
B
CH
NH2
CH
Describe the stereochemistry of the bromohydrin formed in trans-3-Hexene 1 Br2/H2O reaction ( reaction is stereospecific).
Chapter 11 Solutions
Organic Chemistry
Ch. 11.1 - Prob. 1PCh. 11.2 - Prob. 2PCh. 11.2 - Prob. 3PCh. 11.3 - Prob. 4PCh. 11.3 - Prob. 5PCh. 11.3 - Rank the following compounds in order of their...Ch. 11.3 - Organic solvents like benzene, ether, and...Ch. 11.4 - Prob. 8PCh. 11.4 - Prob. 9PCh. 11.4 - Prob. 10P
Ch. 11.5 - Rank the following substances in order of their...Ch. 11.5 - 3-Bromo-1-butene and 1-bromo-2-butene undergo SN1...Ch. 11.5 - Prob. 13PCh. 11.6 - Review the mechanism of geraniol biosynthesis...Ch. 11.7 - Prob. 15PCh. 11.7 - What alkyl halides might the following alkenes...Ch. 11.8 - Prob. 17PCh. 11.8 - Prob. 18PCh. 11.9 - Prob. 19PCh. 11.12 - Prob. 20PCh. 11.SE - Prob. 21VCCh. 11.SE - From what alkyl bromide was the following alkyl...Ch. 11.SE - Prob. 23VCCh. 11.SE - Prob. 24VCCh. 11.SE - Prob. 25MPCh. 11.SE - Prob. 26MPCh. 11.SE - Prob. 27MPCh. 11.SE - Prob. 28MPCh. 11.SE - Prob. 29MPCh. 11.SE - Prob. 30MPCh. 11.SE - Prob. 31MPCh. 11.SE - Prob. 32MPCh. 11.SE - Metabolism of S-adenosylhomocysteine (Section...Ch. 11.SE - Reaction of iodoethane with CN- yields a small...Ch. 11.SE - One step in the urea cycle for ridding the body of...Ch. 11.SE - Prob. 36MPCh. 11.SE - Prob. 37MPCh. 11.SE - Propose a mechanism for the following reaction, an...Ch. 11.SE - Prob. 39APCh. 11.SE - The following Walden cycle has been carried out....Ch. 11.SE - Prob. 41APCh. 11.SE - Which reactant in each of the following pairs is...Ch. 11.SE - Prob. 43APCh. 11.SE - Prob. 44APCh. 11.SE - Prob. 45APCh. 11.SE - Prob. 46APCh. 11.SE - Prob. 47APCh. 11.SE - Prob. 48APCh. 11.SE - Propose structures for compounds that fit the...Ch. 11.SE - What products would you expect from the reaction...Ch. 11.SE - Prob. 51APCh. 11.SE - Prob. 52APCh. 11.SE - Prob. 53APCh. 11.SE - Prob. 54APCh. 11.SE - Prob. 55APCh. 11.SE - Order each of the following sets of compounds with...Ch. 11.SE - Order each of the following sets of compounds with...Ch. 11.SE - Prob. 58APCh. 11.SE - Prob. 59APCh. 11.SE - Ethers can often be prepared by SN2 reaction of...Ch. 11.SE - Show the stereochemistry of the epoxide (see...Ch. 11.SE - Prob. 62APCh. 11.SE - In addition to not undergoing substitution...Ch. 11.SE - The tosylate of (2R, 3S)-3-phenyl-2-butanol...Ch. 11.SE - Prob. 65APCh. 11.SE - Prob. 66APCh. 11.SE - Prob. 67APCh. 11.SE - Prob. 68APCh. 11.SE - Prob. 69APCh. 11.SE - (S)-2-Butanol slowly racemizes on standing in...Ch. 11.SE - Reaction of HBr with (R)-3-methyl-3-hexanol leads...Ch. 11.SE - Treatment of 1-bromo-2-deuterio-2-phenylethane...Ch. 11.SE - Prob. 73APCh. 11.SE - Prob. 74APCh. 11.SE - In light of your answer to Problem 11-74, explain...Ch. 11.SE - Prob. 76APCh. 11.SE - Compound X is optically inactive and has the...Ch. 11.SE - When a primary alcohol is treated with...Ch. 11.SE - Prob. 79APCh. 11.SE - Amines are converted into alkenes by a two-step...Ch. 11.SE - The antipsychotic drug flupentixol is prepared by...
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- 4. The Jones oxidation reaction has two basic parts: addition of chromic acid onto the alcohol (step 1) then reaction of the chromate ester to form a carbonyl (step 2). lorisoo |3| Cr-OH 0 НО HO-Cr-OH - + H2О :Cr-OH ОН (Cr+6) (Cr+4) a. Give the curved arrow mechanism for step 2 (reaction of the chromate ester) in this reaction. CH O HOH b. Is carbon oxidized in step 1 or step 2? How can you tell?arrow_forwardWhat is the mechanisms to get from the reactant to the productsarrow_forwardIf ethanol was added to each of the following, which would be ineffective in preparing ethyl benzoate? Benzoyl chloride. Benzoic anhydride. Benzoic acid with catalytic sulfuric acid. Benzamide. What is the stereochemistry of this compound? 2E, 5E 2Z, 5Z 2Z, 5E 2E, 5Zarrow_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_forwardExamine the reaction/mechanism provided for the acid-catalyzed dehydration of 2-methyl-2-butanol. Select all the following statements that are correct. OH H N8=0=2 CO-S-OH h OH₂ eveyron to H لیا 3 + O-S-OH H₂SO4 + H₂O 5 A. Compound 5 is the only alkene produced by the dehydration. B. Compound 5 is the most stable alkene produced. OC. The mechanism will proceed via E2 as shown above. D. The mechanism will proceed via E1 but E2 is shown above.arrow_forwardCompounds with a d10 configuration will not undergo a reductive elimination reaction, why?arrow_forward
- Using the pKa values of the conjugate acids of the leaving groups (the pKa of HBr is -9, and the pKa of H2O is 15.7), explain the difference in reactivity between CH3Br and CH3OH in a nucleophilic substitution reactionarrow_forwardV7arrow_forwardElectrophilic addition of hydroiodic acid to (3S)-3-tert- butoxypent-1-ene gives an unequal mixture of two products [Reaction 1, 99:1 ratio]. The same reaction carried out on (3S)-3-methoxy-pent-1-ene also gave two stereoisomers albeit in a much lower ratio [Reaction 2, 55:45 ratio]. What is the major product for reaction 1? 0 HỌC LỊCH CH₂ OtBu = o OCH₂=CH₂ Product 2 Product 1 H₂C H₂C Y CH₂ OtBu CH₂H₂C CH₂ OCH, HI ECO Ⓒ1Bu Product 1 H₂C CH₁₂ H₂C H + OCH₂ Product 3 CH₂ CH₂ OtBu Product 2 H₂C T CH₂ OCH, Product 4 Reaction 1 99:1 Reaction 2 50:45arrow_forward
- 5-The hydrolysis of a series of ethyl benzoates by hydroxide ion in 85% aqueous ethanol has been investigated. A Hammett plot of the second order rate constants (Ku) gave a reaction constant p = 2.56. Calculate how much faster ethyl 4- nitrobenzoate will undergo base catalyzed hydrolysis compared to ethyl benzoate under similar conditions. ON 6-The PKa of p-chlorobenzoic acid is 3.98, and that of benzoic acid 4.19. Calculate o-value of p-chloro group.arrow_forwardWhen a dilute solution of acetaldehyde in D2O containing NaOD is shaken, explain why the methyl hydro-gens are exchanged with deuterium but the hydrogen attached to the carbonyl carbon is not. −ODD2O CH3CHO CD3CHarrow_forwardGive the organic product formed in each of the following reactions, draw a 3-D representation for the product molecule showing the correct configurationarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning