1. Triphenylmethane can be prepared by reacting benzene with chloroform in the presence of AICI3. Propose a mechanism for the reaction: go + CHCl3 AICI 3
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- A step in a synthesis of PGE1 (prostaglandin E1, alprostadil) is the reaction of a trisubstituted cyclohexene with bromine to form a bromolactone. Propose a mechanism for formation of this bromolactone and account for the observed stereochemistry of each substituent on the cyclohexane ring. Alprostadil is used as a 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.Melamine, used as a fire retardant and a component of the writing surface of white boards, can be prepared from s-trichlorotriazine through a series of SNAr reactions with ammonia. The first substitution takes place rapidly at room temperature. The second substitution takes place near 100 °C, and the third substitution requires even higher temperature and pressure. Provide an explanation fatr this reactivity.Tranexamic acid, a drug useful against blood clotting, is prepared commercially from p-methylbenzonitrile. Formulate the steps likely to be used in the synthesis. (Don’t worry about cis-trans isomers; heating to 300 C interconverts the isomers.)
- Aromatic substitution reactions occur by addition of an electrophile such as Br+ to an aromatic ring to yield an allylic carbocation intermediate, followed by loss of H+. Show the structure of the intermediate formed by reaction of benzene with Br+.When 3-methyl-1-butene is reacted with 9-borabicyclo[3.3.1]nonane, the "1-ol" product is formed. What is the detailed reactin scheme for the transformation? Describe the purification procedure.Predict the major products formed when 2- methyl-1-butene reacts with: H2, Pt/25°C. Show the reaction mechanism the given alkene reactions
- Provide a reasonable arrow-pushing mechanism for Reaction 5b, and explain the the stereochemical outcome. 5d belowDeduce the structure of each compound from the information given. All unknowns in this problem have molecularformula C8H12.(a) Upon catalytic hydrogenation, unknown W gives cyclooctane. Ozonolysis of W, followed by reduction with dimethylsulfide, gives octanedioic acid, HOOC¬(CH2)6¬COOH. Draw the structure of WWhat steps are needed to prepare phenylacetylene, C6H5C = CH, from each compound: (a) C6H5CH2CHBr2; (b) C6H5CHBrCH3; (c) C6H5CH2CH2OH?
- LDA/THF, 78°Clongrightarrow Predict the major product of the following a- halogenation/a - alkylation reactions under the given reaction conditions.Oximene and myrcene, two hydrocarbons isolated from alfalfa that have the molecular formula C10H16, both yield 2,6- dimethyloctane when treated with H2 and a Pd catalyst. Ozonolysis of oximene forms (CH3)2C = O, CH2 = O, CH2(CHO)2, and CH3COCHO. Ozonolysis of myrcene yields (CH3)2C = O, CH2 = O, (two equiv), and HCOCH2CH2COCHO. Identify the structures of oximene and myrcene.When (CH3CH2)3CBr is added to CH3OH at room temperature, the product is (CH3O)C(CH2CH3)3. Propose a mechanism(s) for the reactions leading to these products and used curved arrows to show the movement of electrons.