Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Question
Chapter 11.SE, Problem 47AP
Interpretation Introduction
Interpretation:
The product and the stereochemistry of the product has to be explained from the reaction of given nucleophiles with (R)-2-bromooctane.
Concept introduction:
SN2 reaction:
Tosylated compound is reaction with sodium methoxide which undergoes again SN2 type of reaction, the methoxide ion attacks the carbon atom through the back side and provides Inverse configuration of methoxy compound. This is shown below,
Given information:
a.
The reaction is shown below,
b.
The reaction is shown below,
c.
The reaction is shown below,
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
4.35 Formulate the reaction of cyclohexene with (i) Br2 and (ii) meta-chloro-
peroxybenzoic acid followed by H30+. Show the reaction intermediates
and the final products with correct cis or trans stereochemistry.
4.36 What products would you expect to obtain from reaction of cyclohexa-
1,3-diene with each of the following?
(a) 1 mol Br2 in CH2C12
(c) 1 mol DCl (D = deuterium, ²H)
(b) 1 mol HCl
(d) 2 mol H2 over a Pd catalyst
4.37 Predict the products of the following reactions on hex-1-yne:
(a) 1 equiv HBr
?
(b) 1 equiv Cl2
?
(c) H2, Lindlar catalyst
2-Give the structures, including stereochemistry of compounds A and B in the following sequence of
reactions:
OH
O₂N-
-SO₂Cl Pyridine
Compound A
LiBr
Acetone
-Compound B
why do (R)-3-chloro-1-methylcycloprop-1-ene and 5-Bromo-1,3-Cyclohexadiene react differently with cyanide (why doesn't cyanide pass through its usual mechanism for these two products and what did you obtain these specific products)
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
- -Ocimene is a pleasant-smelling hydrocarbon found in the leaves of certain herbs. It has the molecular formula C10H16 and a UV absorption maximum at 232 nm. On hydrogenation with a palladium catalyst, 2,6-dimethyloctane is obtained. Ozonolysis of -ocimene, followed by treatment with zinc and acetic acid, produces the following four fragments: (a) How many double bonds does -ocimene have? (b) Is -ocimene conjugated or nonconjugated? (c) Propose a structure for -ocimene. (d) Write the reactions, showing starting material and products.arrow_forwardPredict the major products (including stereochemistry) when cis-3-methylcyclohexanol reacts with the following reagents.(a) PBr3arrow_forwardReaction of this bicycloalkene with bromine in carbon tetrachloride gives a trans dibro- mide. In both (a) and (b), the bromine atoms are trans to each other. However, only one of these products is formed. CH3 CH3 CH3 Br Br CH,Cl, + Br2 or Br Br (a) (b) Which trans dibromide is formed? How do you account for the fact that it is formed to the exclusion of the other trans dibromide?arrow_forward
- 2. (a) Give the product of the following reaction: Br t-BUOK (b) Using the FMOS of the reacting partners explain why this reaction is expected to occur simply on heating, in the absence of light. (c) Specify the preferred stereoisomer and explain why it is preferred.arrow_forwardPredict the electrocyclic products of the following transformations, indicate the type of reaction and justify the stereochemistry.. CH3 CH3 b) hu A Br hv CH3 NC =-CN hvarrow_forwardCH3 CH3 2 Predict the stereochemistry of each of the following reactions: (a) H3C. (d) CH3 LIAIH4 epoxidation CH2 (е) KMNO4 (b) NaBH4 (c) catalytic CH3 hydrogenationarrow_forward
- For each one of the following reactions, show step by step mechanism of the reactions and indicate the stereochemistry of the products and their relationshiparrow_forwardAssign E or Z stereochemistry to each of the following alkenes, and convert each drawing into a skeletal structure (red = 0, yellow-green = Cl). (a) (b)arrow_forwardPredict the major products of the following reactions, including stereochemistry where appropriate. (a) (R)-butan-2-ol + TsCl in pyridine (b) (S)-2-butyl tosylate + NaBrarrow_forward
- The treatment of (CH3)2C=CHCH2Br with H2O forms B (molecular formula C5H10O) as one of the products. Determine the structure of B from its 1H NMR and IR spectra.arrow_forwardWhen 2-iodo-1,4-dimethylcyclohexane is heated in acetic acid, CH3COOH, a mixture of substitution and elimination products is obtained. Provide structures for all possible products, writing [not drawing] the name of the mechanism by which each one is formed.arrow_forwardFriedel–Crafts alkylation of benzene with (R)-2-chlorobutane and AlCl3 affords sec-butylbenzene. Would you expect the product to exhibit optical activity? Explain, with reference to the mechanism.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
