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Glassware used for distillation, reflux, and other organic chemistry reactions "fit" together by means of specially-ground joints typically incorporated into these pieces of glassware. These ground joints are sometimes referred to as "standard taper" joints, because the joint is designated by a size (or taper), and any piece of standard taper glassware will fit any other piece of glassware with a similar standard taper. The size used in the Organic Chemistry labs is "14/20". Other common sizes include 19/22 and 24/40: the larger the number, the larger the joint size, and the larger the glassware.
Standard taper glassware is in general more expensive than common lab glassware, for 2 reasons. The first is, as mentioned above, each piece must be specially machined to guarantee a fit with any other piece of similar-sized glassware, regardless of where (or when) it was made. The second reason is that this glassware must be made strong enough so that it will not implode under vacuum or crack when heated.
Please refer to the glassware safety page for all kinds of tips on safe handling of glassware. Here's some more information specifically pertaining to ground-joint glassware.