1. He is less tall than Tom.

2. Tom is taller than he.

3. He is less smart than Tom.
4. Tom is smarter than he.

5. He is less big than Tom.
6. Tom is bigger than he.

7. He is less careful than Tom.
8. Tom is more careful than he.

9. He is no thoughtful than Tom.
10. Tom is more thoughtful than he.
=================================
Are they all grammatical?
Is each pair the same in meaning?

The expressions with "less" don't fit in 1, 3, and 5. Here's how I'd revise those:

1. He is shorter than Tom.
2 is fine.

3. He is not as smart as Tom.
4. is fine.

5. He is smaller than Tom.
6. is fine.

7 and 8 are fine.

9 -- I'm not sure. Do you mean this?
He is not as thoughtful as Tom.
10 is correct.

Yes, all of the sentences you provided are grammatically correct.

However, there is a slight issue with the use of pronouns in sentences 2, 4, 6, 8, and 10. To make them grammatically correct, it would be better to use the pronoun "him" instead of "he." This is because in these sentences, "him" is the object of the comparisons.

Now let's analyze the meaning of each pair:

1. He is less tall than Tom. (Comparative)
2. Tom is taller than him. (Comparative)

These two sentences convey the same meaning - that Tom is taller than the first person mentioned.

3. He is less smart than Tom. (Comparative)
4. Tom is smarter than him. (Comparative)

Similar to the previous pair, these sentences mean that Tom is more intelligent than the first person mentioned.

5. He is less big than Tom. (Comparative)
6. Tom is bigger than him. (Comparative)

Again, these two sentences have the same meaning - that Tom has a larger size or is physically bigger than the first person.

7. He is less careful than Tom. (Comparative)
8. Tom is more careful than him. (Comparative)

Similarly, these sentences mean that Tom is more cautious or attentive than the first person mentioned.

9. He is no more thoughtful than Tom. (Comparative)
10. Tom is more thoughtful than him. (Comparative)

Lastly, these sentences express that Tom is more considerate or reflective than the first person.

In conclusion, while the pairs of sentences are grammatically correct, they do not all have the same meaning. Some pairs have the same meaning, but others do not.

1. He is less tall than Tom. (grammatical)

2. Tom is taller than he. (grammatical)

These two sentences have the same meaning. Both indicate that Tom is taller than "he."

3. He is less smart than Tom. (grammatical)
4. Tom is smarter than he. (ungrammatical - should be "Tom is smarter than him.")

These two sentences do not have the same meaning. The first sentence states that he is less smart than Tom, while the second sentence, although ungrammatical, is intended to mean the same thing.

5. He is less big than Tom. (grammatical)
6. Tom is bigger than he. (ungrammatical - should be "Tom is bigger than him.")

These two sentences do not have the same meaning. The first sentence states that he is less big than Tom, while the second sentence, although ungrammatical, is intended to mean the same thing.

7. He is less careful than Tom. (grammatical)
8. Tom is more careful than he. (ungrammatical - should be "Tom is more careful than him.")

These two sentences do not have the same meaning. The first sentence states that he is less careful than Tom, while the second sentence, although ungrammatical, is intended to mean the same thing.

9. He is no thoughtful than Tom. (ungrammatical - should be "He is not more thoughtful than Tom.")
10. Tom is more thoughtful than he. (grammatical)

These two sentences do not have the same meaning. The first sentence is ungrammatical and should be corrected to "He is not more thoughtful than Tom," which would mean that he is less thoughtful than Tom. The second sentence means that Tom is more thoughtful than "he."