9) The below reaction is an example of a in a Et H D CH3 CH3 Heat fashion. H CH3 Et CH3 D a. Electrocyclic ring shift; conrotatory b. Electrocyclic ring shift; disrotatory c. [1,5] sigmatropic rearrangement; suprafacial d. [1,5] sigmatropic rearrangement; antarafacial that proceeds b C oor oor of B. and D have electron density on methoxy

9) The below reaction is an example of a in a Et H D CH3 CH3 Heat fashion. H CH3 Et CH3 D a. Electrocyclic ring shift; conrotatory b. Electrocyclic ring shift; disrotatory c. [1,5] sigmatropic rearrangement; suprafacial d. [1,5] sigmatropic rearrangement; antarafacial that proceeds b C oor oor of B. and D have electron density on methoxy

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter30: Orbitals And Organic Chemistry: Pericyclic Reactions

Section30.SE: Something Extra

Problem 14MP: Plastic photochromic sunglasses are based on the following reversible rearrangement of a dye inside...

See similar textbooks

Similar questions

Determine the mechanism of nucleophilic substitution of each reaction and draw the products, including stereochemistr CH₂CH3 CI Br + CN d. + CH3COOH a. acetone + -OCH3 e. DMF f. b. C. ||||| a ||||| Br H Br CH2CH2CH3 + CH3OH DMSO H CH3 CI Br + OCH₂CH3 + CH3CH₂OH
Draw the product of reaction
Classify each pericyclic reaction as an electrocyclic reaction, cycloaddition, or sigmatropic rearrangement. Indicate whether the stereochemistry is conrotatory, disrotatory, suprafacial, or antarafacial.
Draw the final major product(s) for each reaction in the designated box. Indicate stereochemistry Page 7 WInen applicable. Br TMSCI 1. Mg, Et20 Bu4N F НО EtzN 2. THE 3. HСI (aq) РСС 1. MeMgBr Jones reagent ОН CH2CI2 2. HCI (aq) XS HBr МСРВА NaSH (aq) CH2CI2
2. a. b. d. C. oFor each reaction, draw the product(s) and circle the mechanism(s). Include "major be and “minor" when necessary. Stereochemistry must be included for stereoselective reaction "No reaction" is a possible answer. Br Br ts Br CI ta ха но Br CH3ONa CH₂OH KSH acetone Br₂ hv CH3OH NaCN DMSO ser nongaholds zid) no baard E2 E1 SN1 SN2 X. E2 E1 SN1 SN2 X. E2 E1 SN1 SN2 X. E2 E1 SN1 SN2 X• E2 E1 SN1 SN2 X• E2 E1 SN1 SN2 X.
None
None
6. Reactions: Show the major product(s) for each reaction below. Please clearly indicate stereochemistry when applicable. NO REACTION may be an acceptable answer. a. b. C. d. e. g. h. H H Br Br CI (CH3)3CO™ NH₂ DMSO ecte O + يلم tert-BuO KCN DMSO Br THF DBU OH CH3CO₂ THF DMSO THF
Examine the following pericyclic reactions. For each reaction, tell whether it is an electrocyclic reaction, a cycloaddition reaction, or a sigmatropic rearrangement.
6 of 21 4. Sigmatropic Rearrangements For each reaction: symmetry Indicate which п molecular orbital is the HOMO and its Determine if the rearrangement would be suprafacial or antarafacial Draw an arrow pushing mechanism Draw the structure of the major product Describe the rearrangement e.g. [3,3] type type type type hv hy 6 closure closure closure closure
Draw the major organic product of the reaction shown below. O Ca OH **** + HBr • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. - ] Jn [1 ChemDoodleⓇ 5b
ew fopics] Draw the major organic product of the reaction shown below. H2SO4 HO, • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one. C opy aste [F ChemDoodle