Treatment of (R)-4-chlorocyclohexane with HCl produces a mixture of four products. The mechanism showing the formation of all four products is to be drawn, and it is to be identified which products are optically active. Concept introduction: The electrophilic addition of H + to the C=C double bond produces carbocation intermediate. In the next coordination step, the nucleophile attacks the positively charged C + carbon atom. The carbocation intermediate is a trigonal planar, and the nucleophile can attack the C + from the front (wedge) or from behind (dash). This leads to different products. The position of substituents at other carbons in the substrate remains unchanged. The compound not having any symmetry element is the chiral compound.

Question

(a 4 shows scanning electron microscope (SEM) images of extruded actions of packing bed for two capillary columns of different diameters, al 750 (bottom image) and b) 30-μm-i.d. Both columns are packed with the same stationary phase, spherical particles with 1-um diameter. A) When the columns were prepared, the figure shows that the column with the larger diameter has more packing irregularities. Explain this observation. B) Predict what affect this should have on band broadening and discuss your prediction using the van Deemter terms. C) Does this figure support your explanations in application question 33? Explain why or why not and make any changes in your answers in light of this figure. Figure 4 SEM images of sections of packed columns for a) 750 and b) 30-um-i.d. capillary columns.³

Answer 1

Question

Chapter 11, Problem 11.28P

Interpretation Introduction

Interpretation:

Treatment of (R)-4-chlorocyclohexane with HCl produces a mixture of four products. The mechanism showing the formation of all four products is to be drawn, and it is to be identified which products are optically active.

Concept introduction:

The electrophilic addition of H+ to the C=C double bond produces carbocation intermediate. In the next coordination step, the nucleophile attacks the positively charged C+ carbon atom.

The carbocation intermediate is a trigonal planar, and the nucleophile can attack the C+ from the front (wedge) or from behind (dash). This leads to different products. The position of substituents at other carbons in the substrate remains unchanged.

The compound not having any symmetry element is the chiral compound.

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