Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Question
Chapter 11.4, Problem 8P
Interpretation Introduction
Interpretation:
The reaction of S-3–Chloro-3-methyloctane with acetic acid is stated. The stereochemistry of both the reactant and product is interpreted.
Concept introduction:
SN2 reactions are usually favoured. The reaction would not favour in few cases because of the steric hindrance in substrate (reactant molecule). Due to the steric hindrance in reactant molecule undergoes alternate substitution nucleophilic reaction. The alternate substitution nucleophilic mechanism is called SN1 reaction.
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
What product(s) would you expect from reaction of (S)-3-chloro-3methyloctane with acetic acid? Show the stereochemistry of both reactant and product.
Draw the structure of each product from the reaction of benzene with 2-chloro-1-methylcyclohexane using AlCl 3 as the catalyst and Identify the major product.
Draw the formulas of the reactants and products of the reaction: 2-ethylbutanoyl bromide with excess ethylmagnesium bromide and heating the product with concentrated H2SO4.
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
Similar questions
- Draw the structure of (2Z, 6E)-3-ethyl-7-methyldeca-2, 6-dien-1-ol, the sex pheromone of the codling moth, a common agricultural pest that destroys apple crops. By spraying an apple orchard with this pheromone, the mating of male and female moths is disrupted, and moth populations can be controlled.arrow_forward1,3-Cyclohexadiene and 1,4-cyclohexadiene can be distinguished by reaction with ozone and then treatment with zinc. Draw the structures of the products produced by ozonolysis of the two compounds.arrow_forwardTreatment of a hydrocarbon A (molecular formula C9H18) with Br2 in the presence of light forms alkyl halides B and C, both having molecular formula C9H17Br. Reaction of either B or C with KOC(CH3)3 forms compound D (C9H16) as the major product. Ozonolysis of D forms cyclohexanone and acetone. Identify the structures of A–D.arrow_forward
- Two substitution products result from the reaction between 3-chloro-3-methyl-1- butene with sodium acetate (CH3COO – Na +) in acetic acid under SN1. Identify the products.arrow_forwardAcid-catalyzed dehydration of 3,3-dimethyl-2-butanol gives three alkenes: 2,3-dimethyl-2-butene, 3,3-dimethyl-1-butene, and 2,3-dimethyl-1- butene. Draw the structure of the carbocation intermediate leading to the formation of 2,3-dimethyl-2-butene. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. If more than one structure fits the description, draw them all. Separate structures with + signs from the drop-down menu. C P opy aste ChemDoodle >arrow_forwardAcid-catalyzed dehydration of 3,3-dimethyl-2-butanol gives three alkenes: 2,3-dimethyl-2-butene, 3,3-dimethyl- 1-butene, and 2,3-dimethyl-1-butene. Draw the structure of the carbocation intermediate leading to the formation of 2,3-dimethyl-2-butene. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • If more than one structure fits the description, draw them all. • Separate structures with + signs from the drop-down menu. / H₂C CH₂ CH3 CH3 ChemDoodleⓇ On []arrow_forward
- A certain compound of molecular formula C19H38 was isolated from fish oil and from plankton. On hydrogenation it gave 2,6,10,14-tetramethylpentadecane. Ozonolysis gave (CH3)2C O and a 16-carbon aldehyde. What is the structure of the natural product? What is the structure of the aldehyde?arrow_forwardThe optically active (2R)-2-phenyl-2-butanol reacts in hydrochloric acid to form haloalkanes and alkenes. The substitution reaction is reported to occur with 100% racemization. Give the structures of the enantiomers that form during the substitution and indicate how much of each is formed. Propose a mechanism for the substitution reaction to yield the R product. What reagents would you use to achieve 100% retention of configuration. Two geometric isomers are obtained during the elimination reaction. Explain mechanistically which alkene will be the main product.arrow_forwardOne compound that contributes to the “seashore smell” at beaches in Hawai‘i is dictyopterene D', a component of a brown edible seaweed called limu lipoa. Hydrogenation of dictyopterene D' with excess H2 in the presence of a Pd catalyst forms butylcycloheptane. Ozonolysis with O3 followed by (CH3)2S forms CH2(CHO)2, HCOCH2CH(CHO)2, and CH3CH2CHO. What are possible structures of dictyopterene D'?arrow_forward
- H3C N- H₂NNH₂ H⭑ CH3 H3C IN CH3 Hydrazine reacts with 2,4-pentanedione to yield 3,5-dimethylpyrazole. Including protonations and deprotonations, the reaction takes 12 steps. Write out the mechanism on a sheet of paper and then draw the structure of the product of step 6. • You do not have to consider stereochemistry. •You do not have to explicitly draw H atoms. • Do not include lone pairs in your answer. They will not be considered in the grading. • In an elimination step, include the structure of the leaving group, but draw it in its own sketcher. Separate structures with + signs from the drop-down menu. ? Sn th Previous Nextarrow_forwardThe reaction of (2S)-2-chloro-3-methylpentane with sodium iodide yields two products: (2R)-2-iodo-3-methylpentane and racemic 3-iodo-2-methylpentane. Account for the formation of each of these two products. For each product, you should show how it is formed and what that tells you about the mechanism of that specific reaction.arrow_forwardDraw the organic product obtained by hydroboration-oxidation of each of the following alkenes: (a) trans-2-pentene, (b) 2-tert-butyl-3,3-dimethyl-1- butene, and (c) 1-methylcyclohexene. Having done this, draw the product of the acid-catalyzed hydration of these same alkenes. How do the reaction products differ?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