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
OWL V2 with MindTap Reader and Student Solutions Manual eBook for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition
- Draw the products of each reaction. CHO Br. OCH3 Br2 so3 a. -CN i. H2SO, FeBr3 H2SO4 CH3 NaSCH,CH3 CH,COCI j. AICI3 HNO. b. f. -NHCOCH, -F H2SO, "NO2 CH3O но NO2 CH3 NO2 So3 H2SO, HNO3 H2SO, C. HO. NO2 CH;CH,CI AICI Cl2 d. C- -ососн h. CH;0- -COOCH3 FeClaarrow_forwardWhy is the bond dissociation energy for the C–C bond in ethane much higher than the bond dissociation energy for the labeled C–C bond in but-1-ene?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_forward
- 1. Nucleophilic addition involving H, CO 2. Nucleophile elimination ?arrow_forwardExplain 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_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, HgSO4 choices:A,DB,CA,B,CA,B,C,Darrow_forwardThese 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_forward
- Q1. 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_forwardWhich of the following reaction may have a different reaction mechanism compared to the others? a. Hydration b. Hydrohalogenation c. Halogenation d. Ether formationarrow_forward13. 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_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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