yes you should wake your sleeping baby and feed him at least for the first 2 months, till he can do it himself. one thing to remember is that you have to count the hours of gap within feeds starting from the time you started feeding, and not when you ended the last feed. this will help you wake up baby every 2 or 3 hours. if you are helping baby latch on while he is still sleeping, make sure the head is in an elevated position to avoid choking, and gently tap the cheeks to get him a little awake. please check this link below to understand more https://www.breastfeeding.asn.au/bfinfo/do-i-need-wake-my-baby-feeds https://www.breastfeedingbasics.com/articles/waking-a-sleepy-baby
depending on whether your baby is in the first few weeks or is about 2 months or so, you may or may not have to wake up baby. in the initial first few weeks, your baby should be fed every 2 hours, so that he gets the required amount of nutrition and is able to gain the right weight. by the time he is 2 or 3 months old, he will be able to understand the feed on demand concept, and will mostly wake up for feed himself.
The answer is - yes - if he sleeps for more than 4 hours at a stretch. Young babies shouldn't be left hungry. http://www.mayoclinic.org/healthy-lifestyle/infant-and-toddler-health/expert-answers/newborn/faq-20057752
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You may need to, especially newborns, to make sure he gets enough nutrients. Newborns need to feed every 2 hours.
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