Consider the following reaction scheme. (a) Draw the major organic product that is produced in this reaction.

http://www.webassign.net/ksorgchem2/221-20-005c.jpg

(b) Is the reactant optically active?
Yes
No

(c) Is the product optically active?
Yes
No

The reactant is optically active because it consists of a single enantiomer of a chiral compound. We can tell it is chiral because if we draw its mirror image we see that it is not superimposable on the original structure.

This is a SN1 reaction and produces roughly equal amounts of the retention and inversion products. In the retention product, the OH is simply replaced by a Cl. The inversion product is the same except that the wedged and dashed bonds are switched. Because the optical rotation of one enantiomer cancels out that of the other, the product mixture will not be optically active.

This reaction will undergo an Sn1 substitution mechanism, which will lead to formation of the racemic form of the chloride. The reagent is optically active, but the product will not because there will be equal amounts of both enantiomers.