Additions to C-X &pgr;-Bonds, Part 1, Volume 1 by S.L. Schreiber

By S.L. Schreiber

Quantity 1 presents a close survey of reactions that entail the 1,2-addition of nonstabilized carbanion equivalents of carbonyl, imino and thiocarbonyl performance. Emphasis has been put on these reagents that bring about hugely selective addition reactions. equipment are said to choose, for instance, one carbonyl crew over one other within the related molecule, or so as to add preferentially a fraction to 1 (enantiotopic of diastereotopic) face of a carbonyl workforce. strategies that end result from an preliminary addition to the C=X sensible crew, for instance alkenations and rearrangements, also are lined during this quantity.

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Extra resources for Additions to C-X &pgr;-Bonds, Part 1, Volume 1

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2,2,5,5-Tetramethylhexane (c) An isopropyl group is bulkier than a methyl group, and will have a greater preference for an equatorial orientation in the most stable conformation of cis-1-isopropyl-3-methylcyclohexane. Draw a chair conformation of cyclohexane, and place an isopropyl group in an equatorial position. H 1 CH(CH3)2 3 Notice that the equatorial isopropyl group is down on the carbon atom to which it is attached. Add a methyl group to C-3 so that it is also down. H H CH(CH3)2 H3C (d) Both substituents are equatorial in the most stable conformation of cis-1-isopropyl-3-methylcyclohexane.

The methyl groups are rather close together in A, resulting in van der Waals strain between them. In B, the methyl groups are farther apart. Van der Waals strain between cis methyl groups. CH3 Methyl groups remain cis, but are far apart. 25 (a) CH3 H B By rewriting the structures in a form that shows the order of their atomic connections, it is apparent that the two structures are constitutional isomers. CH3 H CH3 H is equivalent to H3C CH3 CH3CCH3 CH3 H (2,2-Dimethylpropane) CH3 H H H3C H CH3 is equivalent to CH3CH2CHCH3 CH3 (2-Methylbutane) Back Forward Main Menu TOC Study Guide TOC Student OLC MHHE Website 54 CONFORMATIONS OF ALKANES AND CYCLOALKANES (b) (c) Both models represent alkanes of molecular formula C6H14.

Butane evolves more heat when it is burned than does an equal volume of methane. 35 When comparing heats of combustion of alkanes, two factors are of importance: 1. The heats of combustion of alkanes increase as the number of carbon atoms increases. 2. An unbranched alkane has a greater heat of combustion than a branched isomer. (a) In the group hexane, heptane, and octane, three unbranched alkanes are being compared. Octane (C8H18) has the most carbons and has the greatest heat of combustion. Hexane (C6H14) has the fewest carbons and the lowest heat of combustion.

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