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I am trying to figure out how to use whose to indicate possession.

Which of these sentences are grammatically correct?

(1) That is the friend who sold me his car.
(2) That is the friend whose car sold to me.

(3) I have to call my friend I accidentally picked up his umbrella after the meeting.
(4) I have to call my friend whose umbrella I accidentally picked up after the meeting.

(5) I met a woman at the party I went to school with his brother.
(6) I met a woman at the party whose brother went to school with me.

(7) The man I bought his car, I saw him on the beach.
(8) The man whose car I bought, I saw him on the beach.

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  • 2
    This is Off Topic proofreading (and/or too many questions in a single post).
    – FumbleFingers
    Commented Jan 24, 2023 at 17:19
  • I am wondering if you got these sentences from a textbook, or if you made them up yourself. Your question could be improved if you added more information about where these came from.
    – J.R. ♦
    Commented Jan 25, 2023 at 10:17

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(1) That is the friend who sold me his car.
(2) That is the friend whose car sold to me.

The top sentence is fine. The bottom sentence isn't quite right, but you could easily fix that if you wanted to use the word whose:

That is the friend whose car I bought.

(3) I have to call my friend I accidentally picked up his umbrella after the meeting.
(4) I have to call my friend whose umbrella I accidentally picked up after the meeting.

The bottom sentence is fine. The top sentence would be better as two sentences, or punctuated with a semicolon:

I have to call my friend. I accidentally picked up his umbrella after the meeting.
I have to call my friend; I accidentally picked up his umbrella after the meeting.

The same is true with sentences #5 and #6. The use of whose is correct, but the initial sentence is a run-on sentence:

A run-on sentence occurs when two or more independent clauses (also known as complete sentences) are connected improperly.

You can read more about how to correct run-on sentences at this website.

(7) The man I bought his car, I saw him on the beach.
(8) The man whose car I bought, I saw him on the beach.

The bottom sentence is acceptable while the top is not.

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  • (2) could also be: "That is the friend whose car was sold to me."
    – alphabet
    Commented Jan 25, 2023 at 23:50
  • Also, your substitute for (8) may be incorrect, since "the man...bought" is syntactically disconnected from the rest of the sentence.
    – alphabet
    Commented Jan 25, 2023 at 23:52
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#2 is syntactically incorrect because "sell" is a transitive verb and requires an object.

That is the friend whose brother sold me a car.

But that sentence as originally written also makes no sense because cars do not engage in buying and selling.

#7 is syntactically incorrect because the noun "man" is neither the subject of a verb nor the object of a verb or preposition. It has no defined syntactic role.

The sentence can be fixed by using a subordinate clause

I saw on the the beach the man whose car I bought.

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