Question 4 Rank the carbocations in Figure 4 in order of increasing stability. Format of answer. A

G.60.

ited Draw both resonance structures of the most stable carbocation intermediate in the reaction shown. od m... • You do not have to consider stereochemistry. . Do not include anionic counter-ions, e.g., I', in your answer. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom Separate resonance structures using the → symbol from the drop-down menu. ● CH4 + ? HBr

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6) Rank the stability of the following carbocations (1 = most stable) To

Rank in order of stability from least to most stable. 1. I. II.

The carbocation intermediate formed in the first step is resonance-stabilized. Draw the other resonance structure (by modifying the provided drawing) and add curved arrow(s) to convert the first resonance structure into the second one. Use the +/- tools to add/remove charges, and use the single bond tool to interconvert between double and single bonds. ÇH3 CH3 H3C. H,C. CH3 CH3 ČH3 ČH3 ČH3 ČH3 Edit Drawing

Rank from least stable to most stable

Build a model of methylcyclohexane, and use the model to complete the following Newmanprojections of methylcyclohexane in the chair conformation: a. When the methyl group is in an axial or equatorial (circle one) position, the molecule is inits lowest potential energy conformation. b. Label one Newman projection above anti and the other gauche to describe the relationshipbetween the methyl group and C3 of the ring. c. In general, which is a lower PE conformation, anti or gauche? d. Explain how your answer to b and c provide an explanation for why it is more favorable fora large group to be in an equatorial than an axial position.

Draw both resonance structures of the most stable carbocation intermediate in the reaction shown. Do not include the halide anion. Let Marvin JS adjust the number of hydrogens automatically as you use the charge tool to specify formal charge. + HCI Marvin JS - Troubleshooting Marvin JS - Compatibility