Do the resistors fail to distribute voltage?
Check the polarity of the diode and double check the pins







simulate this circuit &ndash; Schematic created using CircuitLab

EDIT:



Source: https://www.vishay.com/docs/83760/tcrt5000.pdf

Check the pinout of the device, if the photo transistor is 'on' then the 10k resistor should measure near 0V.

The C pin of the transistor side should be connected to the 10K resistor. The E pin connected to ground. 

The A pin of the LED should be connected to the 330 Ohm LED and the C pin of the LED connected to ground. The forward voltage on the LED should be around 1V to 1.25V. Across the resistor it should be 3.75V to 3V