When 2-bromobutane is reacted with CH3O-, two alkene products, namely 2-butene and 1-butene are obtained. Explain why the E2 reaction produces 2-butene as the major product (80%) and 1-butene as the minor product (20%)

When 2-bromobutane is reacted with CH3O-, two alkene products, namely 2-butene and 1-butene are obtained. Explain why the E2 reaction produces 2-butene as the major product (80%) and 1-butene as the minor product (20%)

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter20: Dienes, Conjugated Systems, And Pericyclic Reactions

Section: Chapter Questions

Problem 20.42P: Bicyclo-2,5-heptadiene can be prepared in two steps from cyclopentadiene and vinyl chloride. Provide...

See similar textbooks

Related questions

Q: What is the molecular orbital diagram of 2,4,6,8-decatetraenes for photochemical reactions. Indicate…

A: Answer -

Q: eDE . Consider the conjugated dienes with the formula C6H10: II III IV V VI VII VIII a)Imagine that…

A: Diels-Alder reaction: The Diels–Alder reaction is a pericyclic reaction (cycloaddition) between a…

Q: Propane reacts with bromine to produce 2-bromopropane and 1-bromopropane (a) State the condition…

A: Substitution reaction: when alkane or alkene is react with halogens in the presence of heat or…

Q: What is the function of CH2Cl2 in the bromination reactions? Why can it fulfill this role?

A: Given : Bromination reactions. To find : Function of CH2Cl2. Solution : As we know that, bromine is…

Q: CH3 -CH3 CH3

Q: Pure (S)-2-bromo-2-fluorobutane reacts with methoxide ion in methanol to give a mixture of…

A: Elimination reaction is the reaction in which 2 atoms in a molecule is eliminated and a double bond…

Q: Give the structure, exclusive of stereochemistry, of the principal organic product formed on…

A: Hello. Since your question has multiple sub-parts, we will solve first three sub-parts for you. If…

Q: Cyclopentadiene is unusually acidic for a hydrocarbon. Which of the following explains why that is?…

A: The solution is given below -

Q: One equivalent of 1,3-butadiene reacts with the quinone below to produce a single product. Why is…

A: In Diels alder reaction,diene reacts with dienophile.

Q: Chemistry Give the products of the reaction of 1 mole of 2-methy1-1,3-pentadiene with 1 mole of…

Q: Chlordane, like DDT, is an alkyl halide that was used as an insecticide for crops such as corn and…

A: The other reactant is cyclopentadiene.

Q: Show that [4+4] cycloaddition of two butadiene molecules to give cycloocta-1,5-diene is thermally…

Q: Why do cis-1-bromo-2-ethylcyclohexane and trans-1-bromo-2-ethylcyclohexane form different major…

Q: 5. Provide an example of/structure for: [a] the endo cycloadduct derived from the Diels-Alder…

A: Three questions about cyclic structures whose example or structure is to be determined.

Q: Highlight on structure and bonding in Alkenes. 2. Draw the structure of 1,5 pentadiene (isolated…

A: The alkenes comprise a series of compounds that are composed of carbon and hydrogen atoms with at…

Q: rentiate between El and E2 reactions by giving one example of each. E2 d) Draw the molecular orbital…

A: A chemical reaction in which the elimination of atoms from the reactant molecule takes place and…

Q: Addition of HBr to 3,3-dimethyl-1-butene gives a mixture of two isomeric alkyl bromide products.…

A: Hydrogen bromide reacts with an alkene to form alkyl bromide. The reaction completes in two steps…

Q: Electrophilic addition to an alkene proceeds via Markovnikov regiochemistry due to the formation of…

Q: reaction of either 3-bromo-1-butene or (Z) -1-bromo-2-butene with water under SN1 condition yields…

A: To explain why reaction of 3-bromo-1-butene or (Z)-1-bromo-2-butene with water under SN1 gives the…

Q: In the alkene below, why is HB more easily abstracted by a halogen atom than HẠ ? НА HB A.…

Q: Given the following compounds: 1-bromopropane, 1-chloropropane, 2-chlorobutane, and…

A: There are some molecules : a) 1-bromopropane b) 1-chloropropane c) 2-chlorobutane and d)…

Q: OMe TMSO OMe COOMe IV NO₂ A سوس COOMe B C NMez DO

Q: Addition of HCI to the unsymmetrical alkene below could potentially give rise to two products. C2H5.…

A: Addition of HCl to the unsymmetrical alkene is an electrophilic addition and occurs through…

Q: 1) Which of the diene isomers is not suitable for 1,2- and 1,4-addition as well as [4+2]…

Q: Which compound is obtained when Buta-1,3- diene undergoes 1,4 addition with HBr? A 2-Bromobut-3-ene…

A: We have to predict the product of given reaction.

Q: Draw the structure of the conjugated diene that will react with one equivalent of HBr to yield a…

A: Addition of HBr to alkene proceed as follows, at first H+ is added to the alkene . Then Br- is added…

Q: Identify the diene and dienophile that will yield the given product in a Diels-Alder reaction, and…

Q: Consider the reaction of chloro, bromo, and iodocyclohexane with KOH to give the eliminatic product…

A: a) Iodide, which is the least basic of the four common halides (F, Cl, Br, and I), is the best…

Q: Rank each group of compounds in order of increasing heat of hydrogenation.(a) hexa-1,2-diene;…

A: Heat of hydrogenation is defined as enthalpy change during the conversion of unsaturated compound to…

Q: 3-bromo-1-pentene and 1-bromo-2-pentene undergo SN1 reaction at almost the same rate, but one is a…

A: Generally, alkyl halide or alcohols undergo elimination reaction which give rise to alkene.…

Q: Addition of HCI to 1-methoxycyclohexene yields 1-chloro-1-methoxycyclo- hexane as the sole product.…

Q: cis-1-Bromo-4-tert-butylcyclohexane and trans-1-bromo-4-tert-butylcyclohexane both react with sodium…

A: When the groups attached are either at 1,2-Cis or 1,4-Cis then the most stable product formed will…

Q: diethyl

A: We know that, when ethers are treated with strong acid in the presence of a nucleophile, they can be…

Q: Draw out both reactants and the Diels-Alder products from reaction of the followin a. furan and…

Q: SNAME and DRAW the STRUCTURE of ALL the alkenes which could undergo catalytic hydrogenation at 900°C…

A: Four alkenes are possible which on catalytic hydrogenation gives methyl cyclopentane. All the…

Q: In the reaction below, 3-Buten-2-one reacts with 2,3-Dimethyl-1,3-butadieneand 1,3-Butadieneat 140°C…

A: A question based on Diel's-Alder reaction, which is to be accomplished.

Q: CH, -CH=CCH=CHCH3 The Wittig reaction can be used for the synthesis of conjugated dienes. Propose a…

A: The wittig reagent and the aldehydes used to synthesize the double bond denoted b is given below

Q: Explain why α-pyrone reacts with Br2 to yield a substitution product (like benzene does), rather…

A: The given compound is aromatic as it involves delocalization of pi-electrons.

Q: Write a general rule that can be used to predict the major product of a Diels–Alder reaction between…

A: The major product formed in Diels-Alder reaction is that in which EWG on alkene and EDG on diene are…

Q: How many linear dienes have molecular formula C6H10? (Disregard cis–trans isomers.) A. How many of…

A: Please find below the pics of all possible linear dienes in C6H10

Q: Diels–Alder reaction of a monosubstituted diene (such as CH2=CH–CH=CHOCH3) with a monosubstituted…

Q: Which isomer of 1-bromo-3-isopropylcyclohexane reacts faster when refluxed with potassium…

A: The isopropyl is a bulky group so it is in equatorial I both cis and trans isomers. In E2…

Q: Identify the type of the following reaction: production of trans- and cis-2-butene from…

Q: Diels—Alder reaction of a monosubstituted diene (such as CH2 = CH – CH = CHOCH3) with a…

A: Diels Alder recation is a concerted reaction between a diene and a dienophile. It usually results in…

Q: The Wittig reaction can be used for the synthesis of conjugated dienes, as, for example,…

Concept explainers

Reactions of Ethers

Ethers (R-O-R’) are compounds formed by replacing hydrogen atoms of an alcohol (R-OH compound) or a phenol (C6H5OH) by an aryl/ acyl group (functional group after removing single hydrogen from an aromatic ring). In this section, reaction, preparation and behavior of ethers are discussed in the context of organic chemistry.

Epoxides

Epoxides are a special class of cyclic ethers which are an important functional group in organic chemistry and generate reactive centers due to their unusual high reactivity. Due to their high reactivity, epoxides are considered to be toxic and mutagenic.

Williamson Ether Synthesis

An organic reaction in which an organohalide and a deprotonated alcohol forms ether is known as Williamson ether synthesis. Alexander Williamson developed the Williamson ether synthesis in 1850. The formation of ether in this synthesis is an SN2 reaction.

Question

Definition Definition Organic compounds that contain at least one double bond between carbon-carbon atoms. The general molecular formula for alkenes with one double bond is C n H 2n .

Expert Solution

This question has been solved!

Explore an expertly crafted, step-by-step solution for a thorough understanding of key concepts.

This is a popular solution!

SEE SOLUTION Check out a sample Q&A here

Step 1

VIEW

Step 2

VIEW

Trending now

This is a popular solution!

Step by step

Solved in 2 steps

SEE SOLUTION Check out a sample Q&A here

Knowledge Booster

Learn more about

Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.

Similar questions

Addition of HBr to allene (CH2=C=CH2) forms 2-bromoprop-1-ene rather than 3-bromoprop-1-ene, even though 3-bromoprop-1-ene is formed from an allylic carbocation. Considering the arrangement of orbitals in the allene reactant, explain this result.
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.
Elimination of HBr from 2-bromobutane affords a mixture of 1-butene and 2-butene. With sodium ethoxide as base, 2-butene constitutes 81% of the alkene products, but with potassium tert-butoxide, 2-butene constitutes only 67% of the alkene products. Offer an explanation for this difference.
Addition of HBr to allene (CH2=C=CH2) forms 2-bromoprop-1-ene ratherthan 3-bromoprop-1-ene, even though 3-bromoprop-1-ene is formed froman allylic carbocation. Considering the arrangement of orbitals in theallene reactant, explain this result.
Four alkenes are formed from the E1 reaction of 3-bromo-2,3-dimethylpentane and methanol. Draw the structures of the alkenes and rank them according to the amount that would be formed.
Fill in the following missing organic structures. Consider stereochemistry (R/S and/or E/Z –cis/trans) and possible carbocation rearrangements.
(dehydrobromination) A chemist carried out an elimination reaction of 1,1-dimethyl-2- bromocyclopentane. The chemist expected the reaction to yield alkene Z as product. However, alkene Z DID NOT form. Instead, three alkenes were produced: one alkene was the major product, the other two alkenes was the minor products. What was the major alkene product that formed? Br Select one: A. I B. II C. IV D. III alcohol HEAT || Z = + (HBr) IV
Bicyclo-2,5-heptadiene can be prepared in two steps from cyclopentadiene and vinyl chloride. Provide a mechanism for each step.
When the alkene A was treated first with Hg(OAc)2 in MeOH and second with NaBH4 the product was the ether B. Using curved arrows please give the mechanism for the first step of (Hg(OAc)2 in MeOH) this reaction, including any regioselectivity or stereoselectivity. H3C 1. Hg(OAc)2, MeOH H3C O-CH3 =CH2 ✓ -CH3 H3C 2. NaBH H3C A B
Which compound is obtained when Buta-1,3- diene undergoes 1,4 addition with HBr? A 2-Bromobut-3-ene B 4-Bromobut-2-ene 1-Bromobut-2-ene D 3-Bromobutene E) 4-bromobutane
Chlordane, like DDT, is an alkyl halide that was used as an insecticide for crops such as corn and citrus and for lawns. In 1983, it was banned for all uses except against termites, and in 1988, it was banned for use against termites as well. Chlordane can be synthesized from two reactants in one step. One of the reactants is hexachlorocyclopentadiene. What is the other reactant?
NAME and DRAW the STRUCTURE of ALL the alkenes which could undergo catalytic hydrogenation at 900°C to form methylcyclopentane. Circle the alkene with the HIGHEST stability and X the alkene with the HIGHEST heat of hydrogenation. Give reasons for your choice.