(c) In the reaction scheme below, compound D is a bicyclic aromatic heterocycle that is prepared via intermediate C. Compound D has a molecular formula of C10H11N and reacts with acetone to form E, which has a molecular formula of C23H26N2. Draw the structures of C, D and E and provide mechanisms for their formation. O CH₂CH₂ + Br CH3 NaOH (aq) D H3C CH3 H₂SO4 (aq) E

Draw a structural formula for the cycloalkene with the molecular formula CH₁0 that reacts with Cl, to give each compound. (a) Cl x D (b) CI -CH3 H₂C CI (c) Cl (d) Cl XaLa

Propose a series of reactions to synthesize each molecule below and show the structure of the intermediate compounds formed following each step you propose. Do not give handwriting solution.

Predict the products of the following reactions:

Draw the products obtained in each of the following reactions: (c) (a) H₂C H3C CH3 CH 3 CH3 CH 3 HCI CH3OH HCI CH3OH (d) (b) H₂C H3C CH3 CH₂0 CH3OH CH3 CH₂ CH3 CH₂00 CH3OH

A step in a synthesis of PGE1 (prostanglandin E1, alprostadil) is reaction of a trisubstituted cyclohexene with bromine to form a bromolactone. Alprostadil is used as temporary therapy for infants born with congenital heart defects that restrict pulmonary blood flow. It brings about dilation of the ductus arteriosus, which in turn increases blood flow in the lungs and blood oxygenation. Propose a mechanism for formation of This bromolactone, and account for the observed stereochemistry of each substituent on the cyclohexane ring.

Draw the main organic product formed in each of the following reactions: (a) (b) (c) + HNO3 / H₂SO4 O CI CI AICI 3 AICI3

Suggest a mechanism for the following synthesis. Draw and name each step.

meta-Chloroperoxybenzoic acid (m-CPBA) is not the only peroxy acid capable of reacting with alkenes to form epoxides. For the reaction below: H3C H3C + CH3CO3H a Draw the structure of the major organic product derived from the alkene.

Propose a mechanism for the following reaction. Draw out the each step of the reaction including ALL intermediates. CI A CO₂ Et + inte NaO6t EtOH CTS Eta₂c,