Sounds like a worn synchro cone on 5th gear. Gears to be engaged both need to be either stationary or rotating at the same speed. The job of the synchromesh mechanism is to ensure that this is achieved. If a cone is worn you will be engaging the gears before the speeds have been synchronised. This is known in the trade as 'beating the synchro'. Older drivers will remember the days when motor vehicles didn't have synchromesh gearboxes, and driver's had to double declutch to match the speed of the driving gear to the driven gear, or in other words the engine to the driving wheels.
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