ORGANIC CHEMISTRY-PRINT (LL)-W/WILEY
4th Edition
ISBN: 9781119761105
Author: Klein
Publisher: WILEY
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 7, Problem 102IP
(a)
Interpretation Introduction
Interpretation:
A mechanism for the conversion of 1 to 2b must be drawn.
Concept Introduction :
Triphenylmethyl carbocation is a very stable carbocation due to resonance stabilization with three benzene rings.
(b)
Interpretation Introduction
Interpretation:
Conversion of compound 1 to 2 (2a, 2b and 2c) is instantaneous in all the cases must be explained.
Concept Introduction :
Rate determining step for SN1 reaction is the carbocation formation step. It is slowest step. Next step is rapid attack of the nucleophile to the carbocation.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
A student wanted to know whether the greater proximity of the ucleophile to the C-2 carbon in the transition state is what causes the 1,2-addition product to be formed faster when 1,3-butadiene reacts with HCl. Therefore, she decided to investigate the reaction of 2-methyl-1,3-cyclohexadiene with HCl.Her friend told her that she should use 1-methyl-1,3-cyclohexadiene instead. Should she follow her friend’s advice?
6)
Propose a reasonable mechanism for this reaction.
m. G
(C6Hs)3
(C6H5)3P-O
Decide on the mechanism for each substitution, and then pick the solvent that affords the faster reaction.
a.(CH3CH2)2CClCH3 + CH3OH in CH3OH or DMSO
b.CH3CH2CH2Br + −OH in H2O or
c. DMF (CH3CH2)2CHCl + CH3O− in CH3OH or HMPA
Chapter 7 Solutions
ORGANIC CHEMISTRY-PRINT (LL)-W/WILEY
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
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
- A student wanted to know whether the greater proximity of the nucleophile to the C-2 carbon in the transition state is what causes the 1,2-addition product to be formed faster when 1,3-butadiene reacts with HCl. Therefore, she decided to investigate the reaction of 2-methyl-1,3-cyclohexadiene with HCl. Her friend told her that she should use 1-methyl-1,3-cyclohexadiene instead. Should she follow her friend’s advice?arrow_forward6. Draw the kinetic and thermodynamic enolates formed when 3-methylbutan-2-one (aka methyl isopropyl ketone) is treated with a base (Na OCH), for example). Please make sure to draw the oxide form, not the carbanion form. ( Kinetically controlled LDA 3-methylbutan-2-one Na* OCH₂ Thermodynamically controlled enolatearrow_forward6. Venlafaxine, an antidepressant, was found to be metabolically unstable. The Medicinal Chemistry team then decided to deuterate the methyl hydrogens as shown below, a strategy which successfully delivered a more stable deuterated analogue (see the transformation below). Using your knowledge of reaction kinetics, explain why such a subtle change resulted in a significantly metabolically stable analogue. OH OH CH3 CD3 I CD H₂CO D₂CO Venlafaxine (antidepressant) Nonadeuterovenlafaxine (antidepressant) -CH3arrow_forward
- 3. Explain the regioselectivity of the nucleophilic attack of the chloronium ion below. Compare it to nucleophilic attack of an epoxide. H₂C Десня CH₂ Nuc: Nuc:arrow_forwardWhich of the following compounds reacts faster in an elimination reaction with KOH? Also provide the major product(s) (if any) for each elimination reaction. Br Br )...arrow_forwardThe following reaction occurs at room temperature in acidic solution, first formingintermediate A, which then rearranges into final product B .i. Show the mechanism for the formation of Intermediate A. )ii. Show the mechanism for the rearrangement of A to B. Explain why the reaction does NOT occur readily in basic solution using your mechanism from 2.aarrow_forward
- If the alkyl halide in each of these reactions was an alkyl chloride instead of thebromide,A. the reaction rate would decrease.B. a better leaving group would be involved. C. a polar aprotic solvent would be needed.D. ΔG would be decreased.arrow_forward5) Consider the two E2 reactions above. Br Br NaOH DMF heat NaOH DMF heat a. What are the major products for each reaction? b. What is the mechanism for each reaction? c. Which reaction would be faster and why? Use words like "transition-state, intermediate and/or reactant/product stability" in your justification. Draw the reaction coordinate diagram for both to assist in your explanation.arrow_forward1. Write the mechanism for the electrophilic aromatic substitution for nitration of the following compound. Both rings must be accounted for in their individual EAS. 2. Show an energy diagram for the reaction progress for both rings. -Ö: O: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 LearningOrganic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
Coenzymes and cofactors; Author: CH15 SWAYAM Prabha IIT Madras;https://www.youtube.com/watch?v=bubY2Nm7hVM;License: Standard YouTube License, CC-BY
Aromaticity and Huckel's Rule; Author: Professor Dave Explains;https://www.youtube.com/watch?v=7-BguH4_WBQ;License: Standard Youtube License