Is it correct to use "his" in this prepositional phrase?

In this chat message I was attempting to say that I was installing Ubuntu on a friends laptop. What I wrote was,

I had a friend for whom I installed Ubuntu on his laptop.

Grammatically, it seems like it works: if I switch around the sentence a bit, I would still use the same kind of prepositional phrase:

I installed Ubuntu on a friend's laptop for him.

Also, if I simply replace the his for an a, it sounds right:

I had a friend for whom I installed Ubuntu on a laptop.

However, how I initially wrote it, it doesn't sound right. Is what I wrote initially correct, and if not, why not?

Solution 1:

All of the examples given are correct, though they differ slightly in meaning.

In the first two, the use of "his" indicates that the laptop belongs to the friend (and that the friend is male).

In the last example, the use of "a" just indicates that you did your friend a favor by installing Ubuntu on a laptop. It does not specify whether the laptop belongs to the friend or not, nor does it imply the gender of the friend.

Solution 2:

I agree with your judgments about the examples -- specifically, *"I had a friend for whom I installed Ubuntu on his laptop" sounds considerably worse than the other related examples. My reaction to it is like my reaction to examples with resumptive pronouns, so my guess is that the "his" is a resumptive pronoun (see here).

In English, you get a resumptive pronoun when there is a conflict between the requirement that a nominal which is coreferential with the relative pronoun of a relative clause be extracted from the clause, on the one hand, and some other constraint that prevents removing that nominal. In your example, since "who(m)" has been extracted with "for", it and any coreferents should be missing from the relative clause: *"I had a friend for whom I installed Ubuntu on 's laptop", but of course you can't remove just the "NP" part of a "NP's" possessive.

Solution 3:

It's awkward because you're using the relative clause object to refer back to your friend when the focus is really his laptop onto which you installed the OS. You're trying to express two ideas, two objects (for whom, on his laptop) -which sound better with two clauses - in one. This makes the construction inefficient. What you probably want to say is "on whose laptop I installed Ubuntu (for him)". Or better still though it sounds a bit formal, use two relative pronouns with an "and" so you have the two clauses: "I had a friend, /for whom/ and /on whose laptop/ I installed Ubuntu."