Interpretation:
Only the 2E,4E isomer is obtained in practice by opening of trans-3,4-Dimethylcyclobutene by two conrotatory paths to give symmetry-allowed products either (2E,4E)-2,4-hexadiene or (2Z,4Z)-2,4-hexadiene.
Concept introduction:
An electrocyclic ring-opening reaction is a reaction in which a σ bond of a cyclic reactant is cleaved to form a conjugated product with one more π bond. It occurs only when like phases of orbitals can overlap to form a bond. Such a reaction is symmetry allowed. It cannot occur between orbitals of opposite phase. Such a reaction is symmetry forbidden. To form a bond, the p orbitals on the terminal carbons must rotate so that like phases can interact to form the new sigma bond. Two modes of rotation are possible - When like phases of the p orbitals are on the same side of the molecule, the two orbitals must rotate in opposite direction one clockwise and one counterclockwise. Rotation in opposite directions is said to be disrotatory.
When like phases of the p orbitals are on opposite sides of the molecule, the two orbitals must rotate in the same direction both clockwise or both counterclockwise. Rotation in the same direction is said to be conrotatory.
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Chapter 30 Solutions
OWLv2 with Student Solutions Manual eBook, 4 terms (24 months) Printed Access Card for McMurry's Organic Chemistry, 9th
- HAND DRAWarrow_forwardPredict the major products of the following organic reaction: Some important notes: Δ CN ? • Draw the major product, or products, of the reaction in the drawing area below. • If there aren't any products, because no reaction will take place, check the box below the drawing area instead. Be sure to use wedge and dash bonds when necessary, for example to distinguish between major products that are enantiomers. ONO reaction. Click and drag to start drawing a structure.arrow_forwardThe following product was made from diethyl ketone and what other reagent(s)? £ HO 10 2-pentyne 1-butyne and NaNH2 ☐ 1-propanol ☐ pyridine butanal ☐ pentanoatearrow_forward
- Which pair of reagents will form the given product? OH X + Y a. CH3 b. CH2CH3 ༧་་ C. CH3- CH2CH3 d.o6.(རི॰ e. CH3 OCH2CH3 -MgBr f. CH3-MgBr g. CH3CH2-MgBr -C-CH3 CH2CH3arrow_forwardQuestion 3 What best describes the product of the following reaction? 1. CH3CH2MgBr (2 eq) 2. H a new stereocenter will not be formed a new stereocenter will be formed an alkyl halide will result an alkane will result an aromatic compound will result 1 ptsarrow_forwardRank the following from most to least reactive toward nucleophilic attack. 1. [Select] [Select] 2. Acyl halide Aldehyde 3. Carboxylate ion 4. Carboxylic acid Ketone 5. [Select]arrow_forward
- Question 10 1 pts Which of the following is the most accurate nomenclature? 1-hydroxy-1-methyldecane-4,7-dione 2-hydroxy-2-methyldecane-5,8-dione 4,6-dioxo-2-methyldecane-2-ol 9-hydroxy-9-methyldecane-3,6-dione 8-hydroxy-8-methylnonane-3,6-dione OHarrow_forwardCould you please explain whether my thinking is correct or incorrect regarding how I solved it? Please point out any mistakes in detail, with illustrations if needed.arrow_forwardWhat are the most proper reagents to achieve these products? سد 1. 2. OH ○ 1. BrMgC6H6; 2. H+ ○ 1. BrMgCH2CH2CH2CH2CH3; 2. H+ O 1. CH3CH2CHO; 2. H+ O 1. BrMgCH2CH3; 2. H+arrow_forward
- Provide the IUPAC (systematic) name only for the following compound. Dashes, commas, and spaces must be correct. Harrow_forwardPlease use the nernst equation to genereate the Ion Selective Electrode Analysis standard curve within my excel spread sheet. Nernst Equation: E = Eo + m (ln a) Link: https://mnscu-my.sharepoint.com/:x:/g/personal/vi2163ss_go_minnstate_edu/EaREe1-PfGNKq1Cbink6kkYB5lBy05hEaE3mbGPUb22S6w?rtime=zQaSX3xY3Ugarrow_forwarda) b) c) H NaOH heat, dehydration + KOH heat, dehydration NaOH + (CH3)3CCHO heat, dehydration Pharrow_forward
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning