ORGANIC CHEM.(LL)-W/OWL V2 >CUSTOM<
9th Edition
ISBN: 9781337034623
Author: McMurry
Publisher: CENGAGE C
expand_more
expand_more
format_list_bulleted
Question
Chapter 11.2, Problem 3P
Interpretation Introduction
Interpretation:
The product expected during the substitution reaction of [S]-2-bromo4 methyl pentane with HS- ion is to be determined. The stereo chemistry of both the reactant and the product has to be stated.
Concept introduction:
In SN2 reaction when a nucleophile HS- ion approaches the Carbon atom the halide group on the opposite side of the carbon atom leaves immediately by altering the stereochemistry.
To determine:
The SN2 reaction between [S]-2-bromo-4-methylpentane and HS- ion.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
A chemist finds that the addition of (+)@epinephrine to the catalytic reduction of butan2-one gives a product that is slightly optically active, with a specific rotation of +0.45°. Calculate the percentages of (+)@butan@2@ol and (-)@butan@2@ol formed in this reaction.
(1) Draw or illustrate the stereochemistry of the product between 1-Ethyl-1-cyclopentene and Br2 and (2) illustrate the reaction mechanism.
1. Name the major product of the reaction between (S)-2-bromohexane and KCH3COO. Be specific with the configuration. Explain the answer
2. Name the alcohol that will produce the most stable intermediate and the dehydration product 2-methyl-1,3-pentadiene.
Chapter 11 Solutions
ORGANIC CHEM.(LL)-W/OWL V2 >CUSTOM<
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
Similar questions
- The formation of Br2 from NBS first involves the reaction of NBS with HBr to form an iminol intermediate and molecular bromine. The intermediate then undergoes acid-catalyzed tautomerism to form succinimide, the byproduct of the reaction. Propose a curved-arrow mechanism for the conversion of NBS into succinimide that also accounts for the formation of Br2.arrow_forwardOn acid-catalyzed dehydration, 1-butanol (CH3CH2CH2CH2OH) can be converted to 1-butene. Write out an equation for the reaction Assign each the appropriate symbol for the mechanism of the reaction (E1 or E2) Draw a suitable mechanism for the reactionarrow_forwardIdentify the type of the following reaction: production of trans- and cis-2-butene from 2-chlorobutane a. E2 b. E1 c. SN1 d. SN2arrow_forward
- (10pts) Compound A, C10H16, was found to be optically active. On catalytic reduction over a palladium catalyst, 2 equivalents of hydrogen were absorbed, yielding compound B, CioH2o. On ozonolysis of A, two fragments were obtained. One fragment was identified as acetic acid (CHCOOH). The other fragment, compound C, was an optically active carboxylic acid, C8H14O2. Write reactions, and draw the correct structures for A-C, explain your answer in detail.arrow_forwardWhat is the product from the E2 elimination of chloromethylcyclohexane?arrow_forwardWhich of the following alkenes, upon reaction with Br2 in CCl4, produces a meso dibromo product?arrow_forward
- When the compound shown below undergoes acid-catalyzed dehydration, a ring expansionoccurs to give the fused-ring product. What type of intermediate is formed in this reaction?Explain the ring expansion in terms of the reaction mechanismarrow_forward1(a) Explain briefly what is meant by ONE of the following terms (use words and diagrams).(i) Markovnikov’s rule(ii) Transition state 1(b) Draw the mechanism (using structures, arrows and appropriate symbols) for the formation of thefollowing products:arrow_forwardHow combination of Br2 and H2O effectively forms bromohydrinsfrom alkenes ?arrow_forward
- 2. a. Write the complete reaction equation along with all the products that might be formed if 1-bromo-1-methylcyclohexane has an elimination reaction.b. Give the name of all the productsc. Which one is the major products? Give the explaination for your answer by writing the mechanism.arrow_forwardFor parts b and c could you please explain why there is a cis isomer formed and how to know when there will be one. For part e do you have to rearrange the compound to achieve the antiperiplanar orientation? Predict the products formed by sodium hydroxide-promoted dehydrohalogenation of the following compounds. In each case, predict which will be the major product. (b) 2-chlorobutane (c) 3-bromopentane (e) trans-1-bromo-2-methylcyclohexane.arrow_forwardA. In the synthesis of 1-bromobutane, what is the inorganic by-product left in the reaction flask following the distillation? Why was the bromoalkane the bottom layer in the separatory funnel? B. Predict the product when 1-methylcyclohexanol reacts with H2SO4 and KBr. Show the mechanism.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning