Concept explainers
a)
Interpretation:
Whether ethyl chloride is expected to undergo Friedal-Crafts reaction with or without rearrangement is to be stated and explained.
Concept introduction:
Friedal-Crafts reaction is an electrophilic substitution reaction in which an
To state and explain:
Whether ethyl chloride is expected to undergo Friedal- Crafts reaction with or without rearrangement.
b)
Interpretation:
Whether 2-chlorobutane is expected to undergo Friedal-Crafts reaction with or without rearrangement is to be stated and explained.
Concept introduction:
Friedal-Crafts reaction is an electrophilic substitution reaction in which an aromatic compound reacts with an alkyl chloride in the presence of AlCl3 to produce an alkylbenzene. The electrophile in this reaction is an alkyl carbocation. The skeletal rearrangement of the alkyl carbocation electrophile either through a hydride shift or alkyl shift (particularly when a primary alkyl halide is used) can lead to the formation of rearranged product also in this reaction.
To state and explain:
Whether 2-chlorobutane is expected to undergo Friedal-Crafts reaction with or without rearrangement.
c)
Interpretation:
Whether n-propyl chloride is expected to undergo Friedal-Crafts reaction with or without rearrangement is to be stated and explained.
Concept introduction:
Friedal-Crafts reaction is an electrophilic substitution reaction in which an aromatic compound reacts with an alkyl chloride in the presence of AlCl3 to produce an alkylbenzene. The electrophile in this reaction is an alkyl carbocation. The skeletal rearrangement of the alkyl carbocation electrophile either through a hydride shift or alkyl shift, particularly when a primary alkyl halide is used, can lead to the formation of rearranged product also in this reaction.
To state and explain:
Whether n-propyl chloride is expected to undergo Friedal-Crafts reaction with or without rearrangement.
d)
Interpretation:
Whether 1-chloro-2, 2-dimethylpropane is expected to undergo Friedal-Crafts reaction with or without rearrangement is to be stated and explained.
Concept introduction:
Friedal-Crafts reaction is an electrophilic substitution reaction in which an aromatic compound reacts with an alkyl chloride in the presence of AlCl3 to produce an alkylbenzene. The electrophile in this reaction is an alkyl carbocation. The skeletal rearrangement of the alkyl carbocation electrophile either through a hydride shift or alkyl shift, particularly when a primary alkyl halide is used, can lead to the formation of rearranged product also in this reaction.
To state and explain:
Whether 1-chloro-2, 2-dimethylpropane is expected to undergo Friedal-Crafts reaction with or without rearrangement.
e)
Interpretation:
Whether chlorocyclohexane is expected to undergo Friedal Crafts reaction with or without rearrangement is to be stated and explained.
Concept introduction:
Friedal-Crafts reaction is an electrophilic substitution reaction in which an aromatic compound reacts with an alkyl chloride in the presence of AlCl3 to yield an alkylbenzene. The electrophile in this reaction is an alkyl carbocation. The skeletal rearrangement of the alkyl carbocation electrophile either through a hydride shift or alkyl shift, particularly when a primary alkyl halide is used, can lead to the formation of rearranged product also in this reaction.
To state and explain:
Whether chlorocyclohexane is expected to undergo Friedal-Crafts reaction with or without rearrangement.
Trending nowThis is a popular solution!
Chapter 16 Solutions
Organic Chemistry
- Give the major organic product of the following reaction sequences (a-e).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_forwardWhich of the alkyl halide bromide below is/are capable of reacting by E2 elimination?arrow_forward
- A ketone undergoes acid-catalyzed bromination, acid-catalyzed chlorination, racemization, and acid-catalyzed deuterium exchange at the α-carbon. All of these reactions have similar rate constants. What does this tell you about the mechanisms of these reactions?arrow_forwardFriedel–Crafts alkylation of benzene with (R)-2-chlorobutane and AlCl3 affords sec-butylbenzene.a. How many stereogenic centers are present in the product?b. Would you expect the product to exhibit optical activity? Explain, with reference to the mechanism.arrow_forward3c)Referring to the intermediates you drew in problem below explain in detail why no meta product is obtained in the Friedel-Crafts alkylation of chlorobenzene. Draw all pertinent resonance structures to support your argument.arrow_forward
- -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_forwardProvide the structure of the major organic product of the following reaction and? explain the stereochemistry which results in this product. 2-Pentanol reacting with 1.) PBr3, pyridine 2.) NaCNarrow_forwardGive the structure of the possible clasein condensation product from the following reaction. Tell which ,if any you would expect to predominate in each case. (a)CH3CO2Et+CH3CH2CO2Et (b)C6H6CO2Et + C6H5CH2CO2Et (c)EtOCO2Et +Cyclohexanones (d)C6H5CHo +CH3CO2Etarrow_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_forwardBringing together your knowledge of the reaction chemistry of substituted benzenes, suggest a preparative route for conversion of compound A to compound B shown belowarrow_forwardDraw the structure of the desired dibromide product H. ) Propose a reasonable arrow-pushing mechanism for formation of the byproduct I.Use your mechanism to justify the stereochemistry in molecule Iarrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning