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Concept explainers
Interpretation:
The intermediate in the Pinacol rearrangement that can be stabilized by resonance delocalization has to be identified.
Concept Introduction:
Pinacol rearrangement: For all glycols Pinacol rearrangement occurs. Unsymmetrical vicinal
Step 1: Add proton (protonation of Pinacol using acid catalyst).
Step 2: Break a bond to give a stable molecules or ions (formation of carbocation).
Step 3: 1, 2-shift (migration of substituent from
Step 4: deprotonation occurs (take a proton away).
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Chapter 10 Solutions
ORGANIC CHEMISTRY-OWL V2 ACCESS
- At 0°C, the following product composition is observed: product A (80%), product B (20%). At 100°C, the following product composition is observed: product A (25%), product B (75%). 6. Why does addition product A predominate at the lower temperature (0°C)? A. The reaction is equilibrium controlled: product A is more stable than product B, so product A predominates. B. The reaction is kinetically controlled: product A forms faster, so product A predominates. C. Product A predominates because it has more ] electron delocalization than product B. D. Product A is less sterically hindered, so it predominates.arrow_forwardThe following is a concerted, bimolecular reaction: CH3Br + NaCN ->CH3CN + NaBr.a. What is the rate equation for this reaction?b. What happens to the rate of the reaction if [CH3Br] is doubled?c. What happens to the rate of the reaction if [NaCN] is halved?d. What happens to the rate of the reaction if [CH3Br] and [NaCN] are both increased by a factor of five?arrow_forward1. Nucleophilic addition involving H, CO 2. Nucleophile elimination ?arrow_forward
- Explain how you can tell from the energy diagram that the reaction with the catalyst in Fig. 8.4 isfaster than the reaction without the catalyst.arrow_forwardThese reagents can produce ketones with alkynes A. BH3, THF, H2O2 B. KMnO4 C. O3 D. H2SO4, H2O, HgSO4 choices:A,DB,CA,B,CA,B,C,Darrow_forwardWhich is a better nucleophile? a. Br− or Cl− in H2O b. Br− or Cl− in DMSO c. CH3O− or CH3OH in H2O d. CH3O− or CH3OH in DMSO e. HO− or −NH2 in H2O f. HO− or −NH2 in DMSO g. I− or Br− in H2O h. I− or Br− in DMSOarrow_forward
- These reagents can produce ketones with alkynes A. BH3, THF, H2O2 B. KMnO4 C. O3 D. H2SO4, H2O, HgSO4arrow_forwardWhich of the following statements about this reaction is true? + HCI a. The major product under kinetic control is the 1,2 addition product because of the stability of the carbocation intermediate in that pathway. b. The major product under kinetic control is the 1,2 addition product because of a more stable transition state for chloride attack. c. The major product under kinetic control is the 1,4 addition product because of the stability of the carbocation intermediate in that pathway. d. The major product under kinetic control is the 1,4 addition product because of a more stable transition state for chloride attack. e. Neither carbocation stability nor transition state stability for chloride attack play a role in determining the preferred product under kinetic control.arrow_forwardQ1. Which of the following alkyl halides form a substitution product in an SN1 reaction that is different from the substitution product formed in an SN2 reaction? a. CH3 Br I I CH3CHCHCHCH3 CH3 b. CH3 CH3CH₂C-CHCH3 CH3 Br C.+ CH₂Br d. CH3 -Brarrow_forward
- 13. Assuming that the following reaction energy coordinate diagram represents a reaction that involves a carbocation, which position on the curve represents the energy of the carbocation? D. С. Energy А. Е. Reaction progress A) B) C) D) D. E) A. В. С. E. B.arrow_forwardWhich of the following reaction may have a different reaction mechanism compared to the others? a. Hydration b. Hydrohalogenation c. Halogenation d. Ether formationarrow_forwardIdentify the stronger nucleophile in each pair. a. NH3,−NH2 b. CH3NH2, CH3OH c. CH3CO2−, CH3CH2O−arrow_forward
- 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
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