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1. He'd only left her a note on the bedside table of which she had not understood the content.
2. The car in the driveway which has a convertible roof is my new Ferrari.

Both sentences share a similar construction where 'which describes the noun before the immediate noun but the first sentence requires an additional preposition 'of'.
Could you please explain it in an easy to understand way?

Many thanks in advance! This is one of the toughest grammar concepts for me. It may sound really simple to you so please bear with me.
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1. He'd only left her a note on the bedside table of which she had not understood the content.
2. The car in the driveway which has a convertible roof is my new Ferrari.

In the first example, the word 'of'' appears in one of the sentences that have been combined. [He left a note on the table. She hadn't understood the content of the note. That's where the 'of' comes from.]
Does it mean everytime two sentences are combined, an additional preposition will appear? If not, we're back to square one.

This morning, I was awaken by a little girl knocking at the door, [of] whom I've never seen in my life. She told me she was my daughter while my wife was standing next to me.

A dog came running toward me with a toy in its mouth, [of] which it has my name on

If [of] required?
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Hi N2G
I'll butt in if I may. 1. He'd only left her a note on the bedside table of which she had not understood the content. There is a noun in the relative clause and that explains of in this case. I would reword the sentence: He'd only left her a note the content of which she had not understood on the bedside table. Since which has no possessive form, the of-genitive must be used unless we say: whose content.
New2grammarDoes it mean everytime two sentences are combined, an additional preposition will appear? If not, we're back to square one.Wrong conclusion.

This morning, I was awakened by a little girl knocking at the door [of] whom I'd never seen in my life. She told me she was my daughter while my wife was standing next to me. No need for a possessive form in this relative clause.

A dog came running toward me with a toy in its mouth, [of] which it had my name on it. Bad sentence, wrong comma usage. Better: A dog came running toward me. It had a toy with my name on it in its mouth.

If [of] required?
CB

which, of which, among which, to which, about which, for which, ...
Combine The car is big with the following:

The car is blue. > The car which is blue is big. [no preposition before the car]

The car is parked there. > The car which is parked there is big. [no preposition before the car]
I bought the car. > The car which I bought is big. [no preposition before the car]
Helen likes the car. > The car which Helen likes is big. [no preposition before the car]
The workmen repaired the car in two hours. > The car which the workmen repaired in two hours is big. [no preposition before the car]
The strongman picked up the car. > The car which the strongman picked up is big. [no preposition before the car -- pick up is a phrasal verb]
The Smiths auctioned off the car. > The car which the Smiths auctioned off is big. [no preposition before the car -- auction off is a phrasal verb]

Jerry is talking about the car. > The car about which Jerry is talking is big.
I paid $10,000 for the car. > The for which I paid $10,000 is big.
The new puppy is afaid of the car. > The car of which the new puppy is afraid is big.
Robert traveled to Chicago in the car. > The car in which Robert traveled to Chicago is big.
A breeze is blowing through the car. > The car through which a breeze is blowing is big.
I hit a tree with the car. > The car with which I hit a tree is big.
A truck is headed toward the car. > The car toward which a truck is headed is big.
The children danced around the car. > The car around which the children danced is big.
Karen knows the owner of the car. > The car of which Karen knows the owner is big.

Albert lost the key to the car. > The car to which Albert lost the key is big.
Marty had trouble with the car. > The car with which Marty had trouble is big.
Lucy set a book on the car. > The car on which Lucy set a book is big.
There's not enough gas in the car. > The car in which there's not enough gas is big.
A stranger walked up to the car. > The car up to which a stranger walked is big. [up to - a compound preposition]
The stranger ran away from the car. > The car from which the stranger ran away is big. [run away - a phrasal verb]

____
Note that these sentences are for pattern practice only. They are not particularly useful in conversations or in written essays!
CJ
CJ, I loved your explanation. But I'm kind of disappointed with the warning at the bottom of your post. Why did you say that?
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New2grammarWhy did you say that?
Well, it depends how often you want to talk about a big car, I suppose. Emotion: smile If you talk about a big car, then maybe one or two of these might come up in a conversation. And besides, these are fairly formal grammatical structures, and people don't usually speak so formally. You are more likely to come across these structures in written material, and with somewhat more abstract vocabulary about serious topics, not trivial subjects such as someone running away from a car or driving into a tree. Emotion: smile
CJ
I see. Just to get an idea about what is considered formal to you, is my sentence formal enough to use 'of which' or native speakers would rephrase it?

He'd only left her a note on the bedside table of which she had not understood the content.
New2grammarHe'd only left her a note on the bedside table of which she had not understood the content.
This sentence could occur in a short story or novel. It would not likely occur in a casual conversation. Instead, it might be
He left her a note on the table beside the bed, but she didn't understand it.
Or if the past perfect is absolutely necessary in the context.
He'd left her a note on the table beside the bed, but she hadn't understood it.
Or if the "only" idea is absolutely required, a person might add only as in the original or might say

All he did was leave her a note on the table by the bed, but she didn't understand it.
The grammatical structures of ordinary everyday conversation are much simpler than those found in novels and essays.
CJ
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