Interpretation:
The structure of the compound has to be drawn, and Z or E stereochemistry has to be assigned to the product which is underwent E2 reaction with NaOH.
Concept introduction:
Z or E stereochemistry:
The two similar groups (or higher priority groups) are in same side in double bond of
Example:
E2 elimination:
Given information:
The molecule is given in Ball-and-stick model and it undergoes E2 elimination with NaOH.
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Chapter 11 Solutions
Organic Chemistry
- 5. Predict the product(s) of the following E2 reactions. DBNarrow_forwardPredict the products of the following reaction, including stereochemistry. 1) OsO4 2) NaHSO, Write the mechanism and predict the products of the following reaction, including stereochemistry. Br2, H,Oarrow_forwardPredict the major product of the following reaction and draw the resonance structure(s) responsible for the regiochemistry of the reaction. HNO3 ? H2SO4arrow_forward
- Which of the following compounds is most reactive under E2 conditions? Br Br Br Br (A) (B) (C) (D) OCompound C )Compound A Compound D Compound Barrow_forwardPredict the product of the reaction seen below. ° S H:SO + H2O LOH SH LOH O Cyclopentane Sulfidearrow_forwardTreatment of the following stereoisomer of 1-bromo-1,2-diphenylpropane with sodium ethoxide in ethanol gives a single stereoisomer of 1,2-diphenylpropene. H3C H C6H5 CH3CH20 Na* CH3CH2OH Br C6H5 Draw the E2 elimination product of the reaction. Take into account that the starting stereochemistry affects the resulting double bond stereochemistry. • Consider E/Z stereochemistry of alkenes. • Do not show stereochemistry in other cases. • You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one.arrow_forward
- What is the major product from this reaction (including stereochemistry if relevant)? OH Compound O Compound P Compound Q Compound R HO P OH BH 3 THF THF; NaOH, H₂O2 H₂O Q OH ?? I R OHarrow_forwardPropose a plausible mechanism for the following transformation: HO [H3O+] EtOH 19.55 The first three steps of the mechanism involve the formation of The first step is The second step is The third step is eTextbook and Media Save for Later Attemarrow_forwardWhich of the following compounds are generated by the reaction below? он (1) Hg(OAc)2, H20 но. (2) NaBHalethanol OH (A) (B) (C) (D) Compounds A, C and D O Compound B Compounds B and D O Compounds A and D (0)arrow_forward
- A3arrow_forwardCompound X, shown below, spontaneously reacts via an intramolecular SN2 to produce intermediate Y, known as an "aziridinium" ion. In the presence of water, intermediate Y reacts further to form product Z. What is the identity of product Z. OH (A) + En Br O (B) aziridinium ion Y OH (C) H₂O + En Z HOarrow_forwardPredict the stereochemical outcome of the following E2 reaction: CI CIarrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning