ORGANIC CHEMISTRY
4th Edition
ISBN: 9781119745105
Author: Klein
Publisher: WILEY
expand_more
expand_more
format_list_bulleted
Question
Chapter 7, Problem 58PP
Interpretation Introduction
Interpretation:
When sodium hydroxide is used to treat 3-bromo-2,4-dimethylpentane, only one product is produced. The product is to be drawn, and the explanation for why there is only one regiochemical result is to be given.
Concept Introduction :
Tertiary alkyl bromide in presence of polar protic solvent follows the E1 pathway. In this reaction carbocation is formed in the first step followed by abstraction of beta hydrogen takes place in the second step.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
When cyclohexene is reacted with hydrobromic acid in acetic acid, the major product is bromocyclohexane. There is a small amount of cyclohexyl acetate formed. What is the mechanism that forms both compounds? What is the purification procedure that isolates both compounds?
When (R)-3-bromo-2,3-dimethylpentane is treated with NaOH, four different alkenes are formed. Draw all four products and rank them in order of stability.
Acetals are formed from the reaction of two alcohols with a carbonyl under acidic
conditions. Acetal formation is faster with 1,2-ethanediol than with two methanol
molecules.
Choose the factor that explains the difference in reaction rates.
A) The reaction with 1,2-ethanediol has a
lower AH (enthalpy) of reaction.
B) The reaction with 1,2-ethanediol has a
higher AH (enthalpy) of reaction.
C) The reaction with 1,2-ethanediol has a
more favorable entropy of reaction.
Chapter 7 Solutions
ORGANIC CHEMISTRY
Ch. 7.2 - Prob. 1CCCh. 7.3 - Prob. 2CCCh. 7.3 - Prob. 1LTSCh. 7.3 - Prob. 3PTSCh. 7.3 - Prob. 4ATSCh. 7.3 - Prob. 2LTSCh. 7.3 - Prob. 5PTSCh. 7.3 - Prob. 6ATSCh. 7.3 - Prob. 7CCCh. 7.4 - Prob. 8CC
Ch. 7.5 - Prob. 9CCCh. 7.6 - Prob. 10CCCh. 7.6 - Prob. 11CCCh. 7.7 - Prob. 12PTSCh. 7.7 - Prob. 13PTSCh. 7.7 - Prob. 14ATSCh. 7.7 - Prob. 4LTSCh. 7.7 - Prob. 16ATSCh. 7.7 - Prob. 17CCCh. 7.7 - Prob. 18CCCh. 7.7 - Prob. 5LTSCh. 7.7 - Prob. 19PTSCh. 7.7 - Prob. 20ATSCh. 7.8 - Prob. 21PTSCh. 7.8 - Prob. 22ATSCh. 7.8 - Prob. 23CCCh. 7.8 - Prob. 24CCCh. 7.8 - Prob. 25CCCh. 7.8 - Prob. 26CCCh. 7.8 - Prob. 27CCCh. 7.9 - Prob. 7LTSCh. 7.9 - Prob. 29ATSCh. 7.9 - Prob. 30ATSCh. 7.9 - Prob. 31ATSCh. 7.10 - Prob. 32CCCh. 7.10 - Prob. 33CCCh. 7.10 - Prob. 34CCCh. 7.11 - Prob. 8LTSCh. 7.11 - Prob. 35PTSCh. 7.11 - Prob. 36PTSCh. 7.11 - Prob. 37ATSCh. 7.11 - Prob. 9LTSCh. 7.11 - Prob. 40PTSCh. 7.11 - Prob. 41ATSCh. 7.12 - Prob. 42CCCh. 7.12 - Prob. 43CCCh. 7.12 - Prob. 44CCCh. 7.12 - Prob. 45CCCh. 7.12 - Prob. 46CCCh. 7 - Prob. 47PPCh. 7 - Prob. 48PPCh. 7 - Prob. 49PPCh. 7 - Prob. 50PPCh. 7 - Prob. 51PPCh. 7 - Prob. 52PPCh. 7 - Prob. 53PPCh. 7 - Prob. 54PPCh. 7 - Prob. 55PPCh. 7 - Prob. 56PPCh. 7 - Prob. 57PPCh. 7 - Prob. 58PPCh. 7 - Prob. 59PPCh. 7 - Prob. 60PPCh. 7 - Prob. 61PPCh. 7 - Prob. 64PPCh. 7 - Indicate whether you would use NaOEt or tBuOK to...Ch. 7 - Prob. 68PPCh. 7 - Draw a plausible mechanism for each of the...Ch. 7 - Prob. 70PPCh. 7 - Prob. 71PPCh. 7 - Prob. 72PPCh. 7 - Prob. 73PPCh. 7 - Prob. 74PPCh. 7 - Prob. 77PPCh. 7 - Prob. 78PPCh. 7 - Prob. 81ASPCh. 7 - Prob. 87ASPCh. 7 - Prob. 90ASPCh. 7 - Prob. 91IPCh. 7 - Prob. 92IPCh. 7 - Prob. 93IPCh. 7 - Prob. 94IPCh. 7 - Prob. 95IPCh. 7 - Prob. 96IPCh. 7 - Prob. 97IPCh. 7 - Prob. 98IPCh. 7 - Prob. 99IPCh. 7 - Prob. 100IPCh. 7 - Prob. 101IPCh. 7 - Prob. 102IPCh. 7 - Prob. 103IPCh. 7 - Prob. 105IPCh. 7 - Prob. 106IPCh. 7 - Prob. 107IPCh. 7 - Prob. 109IPCh. 7 - Prob. 110CPCh. 7 - Prob. 112CPCh. 7 - Prob. 114CP
Knowledge Booster
Similar questions
- H3C N- H₂NNH₂ H⭑ CH3 H3C IN CH3 Hydrazine reacts with 2,4-pentanedione to yield 3,5-dimethylpyrazole. Including protonations and deprotonations, the reaction takes 12 steps. Write out the mechanism on a sheet of paper and then draw the structure of the product of step 6. • You do not have to consider stereochemistry. •You do not have to explicitly draw H atoms. • Do not include lone pairs in your answer. They will not be considered in the grading. • In an elimination step, include the structure of the leaving group, but draw it in its own sketcher. Separate structures with + signs from the drop-down menu. ? Sn th Previous Nextarrow_forwardWhen trans-2-chloro-1-cyclohexanol is treated with a base, cyclohexene oxide is the product. However, when cis-2-chloro-1-cyclohexanol is treated with a base, the product is cyclohexanone. Why doesn’t the cis isomer yield the oxide?arrow_forwardWhen (R)-3-bromo-2,3-dimethylpentane is treated with sodium hydroxide, four different alkenes are formed. Draw all four products, and rank them in terms of stability.arrow_forward
- explain why cis-2-chloro-1-cyclohexanol yields a cyclohexanone but the trans isomer yields cyclohexene oxidearrow_forwardDraw the structures of the following compound: 1-bromo-4-tert-butyl-7-(1-isopropoxyethyl)-8-methoxy-8-methyl-1,6-diphenyl-2,3-nonandiolarrow_forwardWhen heated, allyl aryl ethers and allyl vinyl ethers undergo a reaction called a Claisen rearrangement, a concerted reorganization of bonding electrons similar to the Diels-Alder reaction. The reaction proceeds through a six-membered, cyclic transition state. Draw the structure of the expected product when this compound undergoes a Claisen rearrangement.arrow_forward
- Draw the substitution product formed when cis-1-bromo-4-methylcyclohexane and hydroxide ion undergo an SN2 reaction.arrow_forwardWhat two enols are formed when pent-2-yne is treated with H2O, H2SO4, and HgSO4? Draw the ketones formed from these enols after tautomerization.arrow_forwardProvide all the reagents and show all structures of the product formed in each step, not just a list of reagents. b) Benzene c) Toluene OHC Ĵ Ĉ COOHarrow_forward
- Using cis- and trans-hex-3-ene, demonstrate that the addition of HCl is not a stereospecic reaction. Draw the structure of the stereoisomers formed from each alkene.arrow_forwardBenzene undergoes electrophilic aromatic substitution reaction with alkyl halide in the presence of Lewis acid like AlCl3arrow_forwardIdentify the product in each reaction, and explain why starting materials with identical functional groups give different products.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning