The cis isomer of 1-bromo-4-tert-butylcyclohexane undergoes E2 elimination about 1,000 times faster than the trans isomer. Explain why the cis isomer reacts faster. Hint: It is not because of steric hindrance. Br + NaOH Fast (H3C),C (H3C);C Br + NaOH Slow (H3C);C' (H3C);C

The cis isomer of 1-bromo-4-tert-butylcyclohexane undergoes E2 elimination about 1,000 times faster than the trans isomer. Explain why the cis isomer reacts faster. Hint: It is not because of steric hindrance. Br + NaOH Fast (H3C),C (H3C);C Br + NaOH Slow (H3C);C' (H3C);C

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

See similar textbooks

Related questions

Q: rank the order of rates of the following concerted substitutions from fastest to slowest

A: The kinetic of SN2 mechanism depends upon the number of factors such as type of solvent (protic or…

Q: Which of these two reactions would go better? Why? HOCH2CH3 (CH3CH2);CBr (CH3CH2)3COCH2CH3 NaOCH2CH3…

A: Nucleophilic substitution biomolecular reaction (SN2): The bimolecular nucleophilic substitution…

Q: Consider the pair of reactions below to answer the following question(s). 70% H₂O a. (CH3)3C-C1…

A: The objective of the question is to determine which of the two given reactions is faster and to…

Q: What are the products of the following reactions if they proceed via the SN1 mechanism? CH2CH3 %3D…

A: a. SN^1 reaction is passing through the formation of carbocation. As carbocation is planar,…

Q: a CH3CH2C =CH CH3 CHg ĊCH3 1. ВнЗ (A 2. Н202 (в) кMпо4 or оз 1. NaNH2, NH3 2. СНзон D H2SO4, H20,…

A: HYDRATION OF ALKYNE With the expansion of water, alkynes can be hydrated to frame enols that…

Q: Which of the following is a key intermediate of the reaction shown in the box?

A: In a Grignard reagent, an alkyl group is attached to the electro positive metal, magnesium, which…

Q: Draw curved arrows for the following reaction step. Arrow-pushing Instructions NOX CH3 H3C-C+ CH3…

A: Information about the question

Q: (1) Identify nucleophile and electrophile (2) Draw mechanistic arrows (3) Identify which elementary…

A: Nucleophile are electron rich species and electrophile are electron deficient species.

Q: THE 2. Н,О, NaOH

A: Solved detaily with full reaction mechanism in step 2.

Q: The products of the given reaction are, E2 CH;CH,Br H,C=CH2

A: In Nitrogen containing Lewis base its lone pair of electron is present in sp2 hybrid orbital ,which…

Q: CN CH2CH3 NACN PQ-6. What is the rate determining step of this reaction? Hirgh H3C OTs acetone H3C…

A: • For SN2 reaction Nucleophile attack from Back side .• In case of SN2…

Q: a. Identify the compound below that reacts the fastest under SN1 conditions (HBr, ELOH). Identify…

A: Given: For SN1 reaction, the formation of more stable intermediate is the fastest reacts under SN1…

Q: NH2 HN-CH ~ 10 X Faster than Reaction B Reaction A DMSO NH2 HN .CH3 Reaction B DMSO NO2 NO2 It is…

A: A. DMSO is a aprotic solvent which favours SN2 pathway. Here, CH3I acts as electrophile while -NH2…

Q: Rank the following substrates in order from slowest Sy1 reaction to the fastest. Br -Br Br A в D…

A: SN1 reaction is commonly known as unimolecular nucleophilic substitution reaction, in this reaction…

Q: Three Steps Stereochemistry is trans 1. LI/NH3 2. NaNH2, (C6H5)CH2Br 3. CН2, Zn(Cu) 1. Na/NH3,…

A: Applying concept of reagents and organic synthesis.

Q: Choose the correct mechanism for the following Syl reaction. + H,O + I- OH2

Q: OH 3°-forms carbocation + HOCH₂CH3 H₂SO4 SN1 Bimolecular condensation works well on 3° carbons.…

Q: Write a rate equation for each reaction, given the indicated mechanism. a. CH,CH2-Br + "OH CH2=CH2 +…

A: Rate of reaction: It can be defined as the change in concentration of reactants and products with…

Q: The fastest method of synthesis of isopropyl methyl ether (below) is: CH3 CH3 CH-0 H3C CH. H;C…

A: The solution is given below -

Q: H3C-C H ethanal CIN: and the electrophile is cyanide ion In the step you have just written, the…

Q: Но CN (CH,),SO, CH,0 CN NaCN dil. NaOH CF3 CF3 CF3 DME H,0 1 2 3 racemic racemic Many steps... CH,O…

Q: CH(CH3)CI CH2CH(CH3)CI i) В ii) 2-fluoro-2-methylpropane 2-iodo-2-methylpropane C D

Q: 5. Draw a detailed arrow pushing mechanism for the following reaction. Is the rate-determining step…

A: When No carbocation is formed then reaction is SN2.if carbocation is formed then reaction is SN1

Q: For each of the following reactions: a) say what is the expected Mechanism sn1 or sn2 and say why.…

A: a) We have to give the mechanisms of the reactions. b) Also, we have to tell the optical activity of…

Q: ne structures oft

Q: In Part 1. choose the most "electron-rich" atom in the reaction below. In Part 2, identify the…

A: The given reaction is a nucleophilic substitution reaction. In this reaction, sodium ethoxide acts…

Q: How would the mechanism of this look like? Could you please draw out the mechanism?

A: This reaction is electrophilic aromatic substitution reaction because generated electrophile attack…

Q: Which is the proper reaction mechanism for the following reaction? F OT F-B F :BF, CH2CH, CH2CH3…

A: Option II

Q: When phenol + tert butyl-chloride + AlCl3 (lewis acid) are added together in a mechanism, how come…

A: The above reaction is electrophilic substitution reaction known as Friendly craft alkylation. OH…

Q: Rank the following molecules in order of increasing relative rate of SN1 reaction with methanol,…

Q: 5. a. Predict the major product for each of the following reactions. Include stereochemistry…

A: For E2 elimination leaving group and beta hydrogen atom in the substrate should be antiperiplanar to…

Q: 27. Draw a representation of the transition state for the following exergonic mechanistic step. ..O…

A: In this equation, we will draw a transition state for given mechanism. How we can draw a transition…

Q: 2) Rank the following series of molecules based on reactivity in an E2 reaction (NaOEt/EtOH). (1=…

A: The basic principle is; the bulky group should always come at equatorial position.The higher the…

Q: While we are at it, let's do the same thing for the second step of the mechanism. Again, what is…

A: In the second step of the mechanism, the enzyme accepts hydrogen from the conjugate acid of…

Q: Br Q 5) Consider the two E2 reactions above. Br NaOH DMF heat NaOH DMF heat a. What are the major…

A: The question is based on organic reactions.We need to identify the product and explain its…

Question

The cis isomer of 1-bromo-4-tert-butylcyclohexane
undergoes E2 elimination about 1,000 times faster than
the trans isomer. Explain why the cis isomer reacts faster.
Hint: It is not because of steric hindrance.
Br
+ NaOH
Fast
(H3C),C
(H3C);C
Br
+ NaOH
Slow
(H3C);C'
(H3C);C

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

Interpretation Introduction:

VIEW

Step 2

VIEW

Trending now

This is a popular solution!

Step by step

Solved in 2 steps with 1 images

SEE SOLUTION Check out a sample Q&A here

Similar questions

:N-CH₂ H Classify the type of elementary step shown below. H-N-CH₂ A) bimolecular elimination B) nucleophilic elimination C) bimolecular nucleophilic substitution D) electrophilic addition E) electrophilic elimination
Which of these react the fastest and why. Thank you.
While we are at it, let's do the same thing for the second step of the mechanism. Again, what is happening with the arrows circled in red below? Cys157 Cys157 Cys157 His296 His296 His296 OH HO HN, N: HN HN -CO2 CH2 he Asn329 Asn329 Asn329- Cys157 His296 LOH LOH HNNH Asn329- O deprotonation of the conjugate acid form of imidazole, followed by general base assistance in decarboxylation nucleophilic addition of the cysteine side chain to imidazole O decarboxylation coupled with the generation of molecular hydrogen (H2) O general acid catalyzed isomerization covalent attachment of the substrate to the enzyme
The reaction below shows a Claisen condensation. O 2 CH3COEt Ethyl ethanoate (ethyl acetate) 1. Eto Na* 2. H₂O, HCI ^nc↔x™ raw curved arrows to show the movement of electrons in the step of the mechanism shown below. Arrow-pushing Instructions :O: O: ·||₂ CH3-COEt + CH₂-COET O CH3CCH₂COEt + EtOH Ethyl 3-oxobutanoate Ethanol (Ethyl acetoacetate) ll.. - :0: :0: || CH3-C-CH₂-C-OEt :OEt A tetrahedral carbonyl addition intermediate
Draw the product of the below reaction, a mechanism and a Molecular Orbital ergy diagram for it. Indicate which levels are used for the reaction. MeO2C hv (light) MeO₂C
Of the given option which is the intermediate in the first mechanistic step of the given reaction and why? Why are the other options incorrect.
(1) Identify nucleophile and electrophile (2) Draw mechanistic arrows (3) Identify which elementary step is occurring
PO-13. Rank from slowest to fastest rate of SN1 substitution. Br Br Br II III (A) I
The substitution of an Iby a Clon H3C-I can occur by two possiblemechanisms:Mechanism I: step 1. H3CI → H3C+ + I- slow stepstep 2. H3C+ + Cl- → H3CCl fast stepMechanism II: step 1. H3CI + Cl- → H3CClI slow stepstep 2. H3CClI → H3CCl + I- fast stepa.) Write a rate law for each reaction.
Please help ?
Draw the reaction mechanism of this reaction and state whether it is a SN1 or SN2 reaction.
Write the rate equation (e.g. rate = k[A][B], rate = k[A], etc.) for each of the 2 reactions below, given the indicated mechanism.