Napoli striker Gonzalo Higuain struck the before Jose Callejon netted a second against Arsene Wenger's side to send Arsenal second in Group F below Borussia Dortmund.
An underwhelming night for Arsenal was compounded when Mikel Arteta was sent off for picking up a second booking with a needless foul on Callejon moments after Higuain lost his marker to roll past Wojciech Szczesny for the 73rd-minute opener.
Callejon netted a second for the hosts at the death, but the Italian side needed another goal to ensure a last-16 berth in place of the north-Londoners.
Going into the game as group leaders, Arsenal's defeat sent them to second in the standings behind Dortmund, who secured a last-ditch win over Marseille in France.
Pick that one out: Gonzalo Higuain celebrates after opening the scoring with little under 20 minutes to play
Scramble: Per Mertesacker (left) and Mathieu Flamini are left flailing as Higuain aims for goal
Pulling the trigger: Higuain aims for Wojciech Szczesny's bottom-left corner to score the opener
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Frustration: Olivier Giroud reacts after Arsenal spurn a chance during the early stages of the game
Up for it: Valon Behrami beats Mesut Ozil to the punch in the final group game in Naples
Strong armed: Laurent Koscielny throws himself into a challenge (left) as Gonzalo Higuain reflects on a miss
Physical: Olivier Giroud is wrestled off the ball by Raul Albiol during the first half
Familiar sight: Arsene Wenger (left) and Rafa Benitez (right) watch the game unfold
Hitting the deck: Mikel Arteta and Mathieu Flamini appeal for a free-kick against Goran Pandev
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Tribute: Arsenal and Napoli stars joined to pay homage to the late Nelson Mandela
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A tad late: Arsenal fans were dropped off after the kick-off in special fan coaches forcing them to miss the start
In the spotlight: Wenger makes his way on to the turf ahead of the game resuming after the break
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