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- š§ Conversational Chatbot Limitations: Syntax vs. Semantics
š§ Conversational Chatbot Limitations: Syntax vs. Semantics
PLUS: How an Ingenious Prompt Illustrates a Core Limitation of OpenAIās ChatGPT

Welcome back AI prodigies!
In todayās Sunday Special:
šThe Turing Test, Revisited
šUnderstanding Understanding
š¦¾The Turing Test for OpenAIās ChatGPT
šKey Takeaway
Read Time: 7 minutes
šKey Terms
Theoretical Computer Science: a subset of computer science that explores fundamental computing principles such as algorithms, computational modeling, and complexity.
Torus: the surface of a donut-shaped geometric object.
š©ŗ PULSE CHECK
Can conversational chatbots draw connections between different concepts?Vote Below to View Live Results |
šTHE TURING TEST, REVISITED
As AI enhances digital interactions and content, separating humans from artificial entities like conversational chatbots, image generation models, and voice cloning software is becoming increasingly difficult. Alan Turing, one of the fathers of theoretical computer science, developed a method known as āThe Turing Testā in 1950. The original version had three participants:
A Computer
A Human Integrator
A Human Foil
The āHuman Interrogatorā attempts to determine which is the āComputerā and the āHuman Foilā by asking a series of questions through a keyboard and display screen. The āHuman Interrogatorā may ask as penetrating and wide-ranging questions as they like, and the āComputerā can do everything possible to force a wrong identification. If the āComputerā can consistently fool the āHuman Interrogator,ā itās considered an intelligent, thinking entity. However, Turingās approach had its limitations.
John Searle, an American philosopher widely noted for his contributions to the philosophy of language and the philosophy of mind, believed thinking meant the ability to speak and understand what one was saying. Syntax relates to the rules for constructing grammatically correct sentences, and semantics refers to understanding what those sentences mean. Searle illustrated this distinction with his famous āChinese Room Argumentā thought experiment.
Imagine youāre inside a room under the door, being fed slips of paper with mysterious symbols. You donāt know what the slips say, but you have a massive manual in the middle of the room that provides instructions for producing an output of symbols based on whatever inputs youāre receiving. So you take the slips of paper youāre getting, look up all the relevant portions of the instruction manual, write out a string of symbols on another piece of paper, and feed it back under the door. Unbeknownst to you, the slips of paper you received conveyed questions in Chinese, and the ones you sent out carried very cogent, human-sounding answers to those questions. To a person outside, the roomās inhabitant (i.e., you) seemed to understand their questions, even though thatās not true. Searle said that engineers can train computers to competently deploy syntax rules for any given language, just as the inhabitants of the Chinese room can use the instruction manual to produce strings of symbols. However, text manipulation isnāt text understanding.
šUNDERSTANDING UNDERSTANDING
Some claim Searle sets an impossibly high standard for semantic understanding. No machine that relies on mathematical predictions can come close to the layered knowledge that humans possess. Humans can conceive of several versions of the āwho, what, when, where, why, and howā for any situation and combine emotion and values with observations to conclude. To others, Searleās thought experiment mistakenly assumes that cognitive processing speed equals understanding.
In How the Mind Works, Steven Pinker, a world-renowned cognitive psychologist, argues that Searle leans too much on human intuition in a context where those intuitions donāt provide helpful guidance. Pinker explains that understanding happens rapidly under normal conditions, but Searleās āChinese Room Argumentā slows the process dramatically. Since slow information processing isnāt the same as understanding, we conclude that fast information processing isnāt understanding either. But suppose a sped-up version of Searleās preposterous story could come true, and we met a person who seemed to converse intelligently in Chinese but was deploying millions of memorized rules in fractions of a second. In that case, weād likely conclude that they understood Chinese. Instead of establishing an essential fact about the nature of thought or consciousness, Pinker argues that Searle is just āexploring facts about the English word understandā and that if an individual makes decisions on par with those who truly āunderstand,ā then their lack of understanding is not worth highlighting.
š¦¾THE TURING TEST FOR OPENAIāS CHATGPT
Searleās view is normative, describing what ought to be the case, whereas Pinkerās position is pragmatic. Genuine thinking involves a reflection on what one is thinking about. And itās a reflection capable of bringing in other domains of knowledge beyond the linguistic. In this mode of reflection, the individual doesnāt just string together symbols that make sense to others; they construct a model of the world that makes sense to them. Conversational chatbots are the fastest version of the āChinese Room Argument.ā Sean M. Carroll, an American theoretical physicist and philosopher, suspected that OpenAIās ChatGPT, no matter how well it imitated a humanās linguistic fluency, didnāt understand human prompts. So, he put it to the test with this prompt:
Imagine weāre playing a modified version of chess where the board is treated as a torus. From any one of the four sides, squares on the directly opposite side are counted as adjacent, and pieces can move in that direction. Is it possible to say whether white or black will generally win this kind of chess match?
OpenAIās ChatGPT provides a long-winded but equivocal answer. It says chess on a torus-shaped board will open up new strategic and tactical possibilities but doesnāt conclude whether white or black chess pieces will be more likely to win relative to a standard, square-shaped chess board. Thatās because OpenAIās ChatGPT analyzes text strings and produces responses in which each subsequent word is most likely to occur based on past words. The result is an answer that āmakes senseā but turns out dead wrong. On the other hand, a human being with spatial reasoning ability pictures a chess board in their mind. They roll it into a cylinder and combine the ends until it forms a donut shape. Then, they notice that white chess pieces will always win since they move first, and the black King chess piece begins the game in check.
šKEY TAKEAWAY
This example demonstrates humansā ability to perform bisociation, a form of creative thinking that requires taking two habitually incompatible frames of reference and finding some point or hinge between them. Humans can combine knowledge of chess and geometry to draw a novel inference about a hypothetical situation, but conversational chatbots canāt. This cognitive limitation of AI models prevents the complete automation of knowledge work.
šFINAL NOTE
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