(a)
Interpretation: The product formed from the
Concept introduction: Sigmatropic rearrangements are pericyclic reactions which involve the migration of sigma bonds. In these reactions, old sigma bonds are broken and new sigma bonds are formed.
Curved arrows aid in determining the movement and flow of electrons in the reaction. The electrons that take part in the
(b)
Interpretation: If the given reaction proceeds in a suprafacial or antarafacial manner under thermal conditions is to be predicted.
Concept introduction: Sigmatropic rearrangements are pericyclic reactions which involve the migration of sigma bonds. In these reactions, old sigma bonds are broken and new sigma bonds are formed.
Curved arrows aid in determining the movement and flow of electrons in the reaction. The electrons that take part in the chemical reactions are shown by the curved arrows.
(c)
Interpretation: If the given reaction proceeds in a suprafacial or antarafacial manner under photochemical conditions is to be predicted.
Concept introduction: Sigmatropic rearrangements are pericyclic reactions which involve the migration of sigma bonds. In these reactions, old sigma bonds are broken and new sigma bonds are formed.
Curved arrows aid in determining the movement and flow of electrons in the reaction. The electrons that take part in the chemical reactions are shown by the curved arrows.
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Chapter 25 Solutions
ORGANIC CHEMISTRY
- Rank the compounds in each group in order of increasing reactivity in electrophilic aromatic substitution: (a) C6H6, C6H5Cl, C6H5CHO; (b) C6H5CH3, C6H5NH2, C6H5CH2NH2.arrow_forwardThe bicyclic alkene P can be prepared by thermal electrocyclic ring closure from cyclodecadiene Q or by photochemical electrocyclic ring closure from cyclodecadiene R. Draw the structures of Q and R, and indicate the stereochemistry of the process by which each reaction occurs.arrow_forwardAddition of HCl to alkene X forms two alkyl halides Y and Z. (A) Label Y and Z as a kinetic or thermodynamic product and explain why. (B) Explain why the addition of HCl occurs at the exocyclic C=C, rather than the other C=Carrow_forward
- (a) When cis-1-bromo-2-methylcyclohexane undergoes an E2 reaction, two products (cycloalkenes) are formed. What are these two cycloalkenes, and which would you expect to be the major product? Write conformational structures showing how each is formed. (b) When rans-1-bromo-2-methylcyclohexane reacts in an E2 reaction, only one cyclo- alkene is formed. What is this product? Write conformational structures showing why it is the only product.arrow_forwardGive the structure, exclusive of stereochemistry, of the principal organic product formed on reaction of 2,3-dimethyl-1,3-butadiene with each of the following:(a) 2 mol H2, platinum catalyst(b) 1 mol HCl (product of 1,2-addition)(c) 1 mol HCl (product of 1,4-addition)(d) 1 mol Br2 (product of 1,2-addition)(e) 1 mol Br2 (product of 1,4-addition)(f) 2 mol Br2arrow_forwardReaction of this bicycloalkene with bromine in carbon tetrachloride gives a trans dibro- mide. In both (a) and (b), the bromine atoms are trans to each other. However, only one of these products is formed. CH3 CH3 CH3 Br Br CH,Cl, + Br2 or Br Br (a) (b) Which trans dibromide is formed? How do you account for the fact that it is formed to the exclusion of the other trans dibromide?arrow_forward
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