Interpretation:
The faster reactant is to be identified from given pairs of reactants with given reagent.
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 given compound is shown below,
The SN2 displacement by I- on CH3Cl and CH3OTos
b.
The given compound is shown below,
The SN2 displacement by CH3COO- on bromoethane or on Bromo cyclohexane.
c.
The given compound is shown below,
The SN2 displacement on 2-bromopropane by CH3CH2O- or by CN-
d.
The given compound is shown below,
The SN2 displacement by CH ≡ C- on bromomethane in benzene or in acetonitrile
Trending nowThis is a popular solution!
Chapter 11 Solutions
Organic Chemistry
- When 3-bromo-1-methylcyclohexene undergoes solvolysis in hot ethanol, two productsare formed. Propose a mechanism that accounts for both of these productsarrow_forwardHow many alkenes yield 2,2,3,4,4−pentamethylpentane on catalytic hydrogenation?arrow_forwardFollowing are diastereomers (A) and (B) of 3-bromo-3,4-dimethylhexane. On treatment with sodium ethoxide in ethanol, each gives 3,4-dimethyl-3-hexene as the major product. One diastereomer gives the E alkene, and the other gives the Z alkene. Which diastereomer gives which alkene? Account for the stereoselectivity of each -elimination.arrow_forward
- Treatment of but-1-ene with hot KMno4/OH- gives product D, and subsequent acidification of the mixture gives product E. What are D and E. Give reaction equations.arrow_forwardThe spirocyclic pentadiene derivative F shown below is converted stereospecificallyinto compound G on heating. The transformation involves two consecutive pericyclicreactions of the same type, and proceeds via compound H which is not isolated. Identify the type of pericyclic reaction occurring, and determine the structure ofcompound H.arrow_forwardElimination occurs when (Z)-3-bromohex-3-ene is treated with NaNH2. Under the same conditions, 1-bromocyclohexeneundergoes elimination much more sluggishly. Explain whyarrow_forward
- (a) Give a mechanism for this reaction, showing how the two products arise as aconsequence of the resonance-stabilized intermediate.(b) The bromination of cyclohexene using NBS gives only one major product, as shown onthe previous page. Explain why there is no second product from an allylic shift.arrow_forwardmost of the additions of bromine to double bonds gave entirely antistereochemistry. Explain why the addition to phenanthrene gives a mixture of synand anti stereochemistry. When the product from (c) is heated, HBr is evolved and 9-bromophenanthrene results.Propose a mechanism for this dehydrohalogenation.arrow_forwardWhen Br2 is added to buta-1,3-diene at -15 °C, the product mixture contains 60% ofproduct A and 40% of product B. When the same reaction takes place at 60 °C, theproduct ratio is 10% A and 90% B.(a) Propose structures for products A and B. (Hint: In many cases, an allylic carbocationis more stable than a bromonium ion.)arrow_forward
- A certain hydrocarbon, C5H6, yields the two products shown below upon ozonolysis with 1. O3/CH2Cl2 2. Zn/H3O . Deduce the structure of the hydrocarbon.arrow_forwardUsing one or more of the following compounds as starting materials or products illustrate, with an example, each of the following type of pericyclic reactions. Your answer should include curved arrow mechanisms. (i) a disrotatory thermal electrocyclic reaction (ii) a conrotatory photochemical electrocyclic reaction (iii) a [4+2] cycloaddition (iv) a [3,3]-sigmatropic rearrangementarrow_forwarda) What product is formed from the [1,7] sigmatropic rearrangement of a deuterium in the following triene? (b) Does this reaction proceed in a suprafacial or antarafacial manner under thermal conditions? (c) Does this reaction proceed in a suprafacial or antarafacial manner under photochemical conditions?arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning