Answered: Explainwhythefollowingdeuterated1-bromo…

Explainwhythefollowingdeuterated1-bromo-2-methylcyclohexaneundergoes dehydrohalogenation by the E2 mechanism, to give only the indicated product. Two other alkenes are not observed.

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

Chapter6: Reactions Of Alkenes

Section: Chapter Questions

Problem 6.27P: Reaction of this bicycloalkene with bromine in carbon tetrachloride gives a trans dibromide. In both...

See similar textbooks

Related questions

Q: Nao (cat.) OEt но f. HCI, H,O HCI, H2O heat g. HCI, NH, then NaCN

Q: Provide the mechanism for the conversion shown below. CH3Li is effectively H3C-Li+. What type of…

A: Given : reaction Step 1: put partial charge on reactant

Q: Elimination occurs when (Z)-3-bromohex-3-ene is treated with NaNH2. Under the same conditions,…

A: The elimination reaction occurs when (Z)-3-bromohex-3-ene is treated with NaNH2 is as shown below.

Q: (a) When (Z)-3-methylhex-3-ene undergoes hydroboration–oxidation, two isomericproducts are formed.…

A: a.

Q: 1-methylcyclohexene is reacted with the following reactants. Write products. Write which…

A: 1 Bromination 2 Formation of cyclopropane

Q: Substitution vs Elimination. Identify the major product/s in the following reactions AND also the…

A: in organic chemistry a reaction can go via different pathway 1) substitution where one functional…

Q: Draw mechanism arrows and then predict the major products and stereochemistry. Also include the…

Q: Addition of hydrochloride acid to 1-isopropenyl-1-methylcyclopentane generates 1-chloro-1,2,2…

Q: What is/are the possible product(s) of dehydrohalogenation of cis-1-bromo-2-ethylcycloheane? Et…

A: Dehydrohalogenation refers to loss of halogen as halide and a hydrogen atom present on carbon beta…

Q: 1/ For each of the molecular formulas, determine the number of elements of unsaturation and draw 3…

A: Note: According to our guidelines we are supposed to answer only one question. Kindly repost other…

Q: t that trans-1-bromo-2-methylcyclohexane yields the non-Zaitsev

Q: Please show the reaction mechanisms of the [3 + 2] cycloadditions of (A) Ozone and (B) OsO4 to…

A: [3 + 2] Cycloaddition is a type of pericyclic reaction in which 1,3-dipolar compounds add to the…

Q: Draw the product F of the reaction shown in Scheme 3, where E undergoes an electrocyclic ring…

A: Cycloaddition reactions are those reactions in which ring closure or ring opening is followed.

Q: CH3H ff. H ÓH + CEN with pyridine in DMSO Reaction Type(s) + Mechanism(s) Product(s).…

A: The answer is given as follows

Q: (SYN) Hydroboration-oxidation can be carried out with deuterated forms of the reagents and solvent.…

A: Hydroboration oxidation is a reaction in which water or D2O attacks on the carbon which has more…

Q: a. Give the mechanism (arrow-pushing) for the reaction below. NaOMe/MeOH b. Name the product of the…

A: a. It follows E1 mechanism. At first the good leaving group Br^- departs to give corresponding…

Q: Q3 formulate clearly the mechanism for euch of the followingreactionsi- a) Alkylation For benzalde…

Q: divls depends oin the moisture content of the reaction mixture. Propose a detailed mechanism for…

Q: Predict the product and write the complete stepwise mechanism. for the following reaction. Show all…

A: NaSCH3 is a conjgate base of methanethiol. It is a powerful nucleophile.

Q: Give the structure of the possible clasein condensation product from the following reaction. Tell…

A: Concept introduction: The Claisen condensation reaction involves a reversible condensation between…

Q: Which of the following is/are the expected product/s of the reaction of 2-pentanone (CH3COCH2CH2CH3)…

A: In a haloform reaction, there must be CH3CO- group.

Q: Draw mechanism arrows and then predict the major products and stereochemistry. Also include the…

Q: mechanism for the of hydrolysis (1-bromo of Propose a reaction methylpropyl)cyclohexane. Including…

A: Stereochemistry is branch of chemistry in which we deal with arrangement of atoms in three…

Q: (d) Carry out the following conversions and provide the mechanism : CH3 HO H3C CH3 -CH3 from H3C H3C…

A: alpha keto carbanions and p-benzoquinoes react to give the product

Q: Use curved arrows to show how E is converted to F by a two-step reaction sequence consisting of a…

A: In sigmatropic rearrangement, the rearrangement of pi bond and the breaking of sigma bond take…

Q: This molecule will undergoa bimolecular nucleophilic substitution reaction with hydraxide ion.…

Q: Nitration of Benzene with H,SO, will produce? O 1-Nitrobenzene O Dioxy ntrogen benzene O All O…

A: Nitration of benzene with H2SO4 will produce Nitrobenzene.

Q: Predict the major organic product for the following reaction. You do not need to account for…

Q: 5. Explain how treatment of the cycloaddition product with an aqueous basic solution of KMnO4 at…

Q: When 1,2-dimethylcyclopentene undergoes hydroboration–oxidation, one diastereomerof the product…

A: A two step reaction that changes conversion of alkene into alcohol. Anti-markovinokov's rule is…

Q: |||| H* I H₂O

Q: Draw the products of attached SN2 reaction and indicate the stereochemistrywhere appropriate.

A: Introduction: SN2 reaction: SN2 reaction means substitution nucleophilic bimolecular reaction. In…

Q: H2O, H+

A: Since you have posted a multiple question so i have first one for you. If you need any specific…

Q: Give synthests, CH2OCCH2C43 WACHCH to. CH3 0 C ਆਟੇ ਦੀ छ // 0 CH3 N i H CH3CH₂C=CH

Q: f.) Draw the SN2 transition state, the product and the leaving group for the given reaction. Include…

Q: The following enamine reacts with electrophiles to afford exclusively the trans-product. 1.…

A: Various compounds are synthesized in organic chemistry using reagents.

Q: Draw the mechanism of the following reaction, using the curved-arrow notation to indicate the…

A: Bromine adds to the double bond to produce cyclic bromonium ion which is attacked by water molecule…

Q: (1R,2R)-1-Bromo-2-methylcyclopentane is reacted with sodium methoxide. Given the product(s) and show…

A: An elimination reaction in organic chemistry is a reaction where a base abstract An acidic proton…

Q: Which of the following statements applies to the E1 mechanism? Mark all that apply. OThe C-H and C-X…

A: Elimination reaction is the reaction in which some by-product eliminate from a reactant to form…

Q: For each reaction, decide whether substitution or elimination (or both) is possible, andpredict the…

A: The reaction of haloalkanes with an electron rich species may either be a nucleophilic substitution…

Q: Draw the product (Y) of the following reaction. Show how the transition state determines the regio-…

A: This is an example of Diels-Alder reaction

Q: Treatment of but-2-yne with NCS affords an interesting molecule with two methoxy groups and two…

Q: The hydrobrominationof 2-methyl-1-butene could theoretically lead to 2 different alkyl bromides; in…

A: We are given an alkenes

Q: In the hydroboration of 1-methylcyclopentene shown in Solved Problem 8-3, the reagentsare achiral,…

A: Enantiomers are the mirror images of each other, which are stereoisomers. Chiral molecules show…

Q: O-O-H A) BH,, THF H,O,, OH B) Br, C) D) two of the above

Q: jo. HOCH₂CH₂OH HC1 & + H₂O

Question

Explainwhythefollowingdeuterated1-bromo-2-methylcyclohexaneundergoes dehydrohalogenation by the E2 mechanism, to give only the indicated product. Two other alkenes are not observed.

2. Explain why the following deuterated 1-bromo-2-methylcyclohexane undergoes
dehydrohalogenation by the E2 mechanism, to give only the indicated product.
Two other alkenes are not observed.
H
H
H
CH,
CH,
-OCH,
CH;
-CH,
Br
H.
H
DH
D H
H
D
observed
not observed
ra

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.

SEE SOLUTION Check out a sample Q&A here

Step 1

VIEW

Step 2

VIEW

Step by step

Solved in 2 steps with 1 images

SEE SOLUTION Check out a sample Q&A here

Knowledge Booster

Selection Rules for Pericyclic Reactions

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

10) What is the major product of the following reactions? CH3 + HCI H₂O H* ? CH3CO3 H HBr 11) Which is more highly regioselective the addition of HCl to methylenecyclohexane or to 1- methylcyclohexene? Explain. What product(s) is/are formed when the following compound react with ozone and then with dimethyl sulfide (i.e. ozonolysis)? a) b)
2. Explain why the following deuterated 1-bromo-2-methylcyclohexane undergoes dehydrohalogenation by the E2 mechanism, to give only the indicated product. Two other alkenes are not observed. H H H CH3 NaOCH3 fCH3 YCH3 CH3 -Br H. H. H. DH D H observed not observed
Q12. (1-bromoethyl)benzene 1 udergoes an elimination following an E1 mechanism. Fill in the following synthetic scheme by drawing the structure of intermediate 2 and product 3. The chemical formula of product 3 is provided as guidance. CH; RDS Br C3Hg E1 2 3
For the following dehydrohalogenation (E2) reaction, draw the major organic product(s), including stereochemistry CI (Cн Сок СH, HII (Cн, СОн
Reaction of this bicycloalkene with bromine in carbon tetrachloride gives a trans dibromide. In both (a) and (b), the bromine atoms are trans to each other. However, only one of these products is formed. Which trans dibromide is formed? How do you account for the fact that it is formed to the exclusion of the other trans dibromide?
1) Draw the complete electron-pushing arrow mechanism for the following reductions. Explain, using resonance contributors (structures), the regiochemistry that results in each case. OMe Na, MeOH ? NH3 CHO Na, MeOH ? NH3
Your task is to convert 2-bromobutane to 1-butene in highest yield. Which reagents would you use? O KOH/H2O O KOH/CH,OH O CH3CH2ONA/CH3CH2OH O CH3ONA/CH3OH O (CH3)3COK/(CH3)3COH
Draw all products of the reaction of (1S,2R)-1-bromo-1,2-dimethylcyclohexane in 80%H2O/20%CH3CH2OHat room temperature..
Given that an E2 reaction proceeds with anti periplanar stereochemistry, draw the products of each elimination. The alkyl halides in (a) and (b) are diastereomers of each other. How are the products of these two reactions related? Recall from Section 3.2A that CgHs- is a phenyl group, a benzene ring bonded to another group. "OCH,CH, b. CgHgC CH Br OCH,CH3 a. Br
What alkene is needed to synthesize the following 1,2-diol using the given reagents? Be sure to answer all parts. CH3CH₂CH2 [1] OsO4 followed by NaHSO3 in H₂O: [2] CH3CO3H followed by "OH in H₂O: H OH OH CH₂CH₂CH3 draw structure... draw structure ...
Identify the lettered compounds in the following reaction scheme. носн сн, он H+ H 1. NaNH, 2. (bromomethyl)cyclopentane Na, NH₂ (1) H₂O+ A B C
iii) 10. For each of the following reactions, provide the structure of the major product and circle the predominant mechanism. Indicate the stereochemistry where necessary. VII) E1 E2 SN1 SN2 E1 E2 SN1 SN2 NaSH DMF H* CH3OH Br (CH3)3COK (CH3)3COH OH iv) HBr viil) E1 E2 E1 E2 SN1 SN2 SN1 SN2