No you cannot do that. You do not own the copy of the songs. Instead, you are given a license to use the songs. According to the iTunes Terms and Conditions:

USAGE RULES

(i) You shall be authorized to use iTunes Products only for personal, noncommercial use.

(ii) You shall be authorized to use iTunes Products on five iTunes-authorized devices at any time, except for Content Rentals (see below).

(iii) You shall be able to store iTunes Products from up to five different Accounts at a time on compatible devices, provided that each iPhone may sync tone iTunes Products with only a single iTunes-authorized device at a time, and syncing an iPhone with a different iTunes-authorized device will cause tone iTunes Products stored on that iPhone to be erased.

(iv) You shall be authorized to burn an audio playlist up to seven times.

(v) You shall not be entitled to burn video iTunes Products or tone iTunes Products.

http://jlaufirm.com

http://jasonlauip.blogspot.com

I disagree with Jason Lau on this one, depending on what you mean by "songs". Section 202 of the Copyright Act makes the fundamental point, which has been part of our Copyright Act for over a century, that there is a big difference between a copy and a copyright. Selling one has no bearing on who owns the other. For example, if I write a song and create a sound recording of it (called a "phonorecord" in the Copyright Act, which includes digital files on CDs, USBs or hard drives), I am the owner of the copyright in "the song" (meaning both the musical composition and the sound recording). If I give you the right to reproduce the sound recording onto your CD-R, you still own your CD-R, which is now called a "phonorecord", and are authorized by law (even if not by me) to sell your CD-R. (17. U.S.C. § 109(a).) If I make 1,000 CDs and sell them, the new owners are authorized to sell them without my permission. If I give permission to 1,000 people to reproduce (e.g., download) my sound recording onto their CD-R, hard drive or USB, each of those 1,000 people has the right to sell the CD-R, hard drive or USB without my permission. If, on the other hand, I sell my copyright in the song (the musical composition and the sound recording), ownership of any pre-existing copies (phonorecords) is not affected.

If you have reproduced a sound recording onto a tangible medium of expression by authority of the copyright owner, that resulting phonorecord is "lawfully made" under the Copyright Act and you, as owner, are entitled to sell that phonorecord without the consent of the copyright holder. (This does NOT mean you have permission to make more copies (phonorecords) or help others make their own phonorecords from yours! That exclusive right to reproduce the work into more phonorecords continues to belong to the copyright holder, subject to several exceptions not applicable to your question.)

Even though the copyright holder can't prevent you from selling copies of a work lawfully made under the Copyright Act, there are two additional points to keep in mind. (1) Many states have what are sometimes called "true name and address" laws that require anyone selling a copy or phonorecord to include the true name and address of the manufacturer (in this case, you) on the outside cover or packaging. (2) You may have a contractual obligation to someone else -- perhaps iTunes itself -- that might obligate you not to do certain things, even though you have a legal right to do them.

Since I'm not your lawyer, I suggest that you consult with one in your community, paying closest attention to (1) 17 U.S.C. § 109(a), (2) any applicable state true name and address statute, and (3) whether any contractual agreements you may have entered into limit your freedom of choice.

But again, I stress, there is a huge difference between selling "a song," "a book" or "a poem" based on whether you are referring to the intangible work of authorship (as in "I wrote a song, "I wrote a book," or "I wrote a poem") or you are referring to the tangible item in which the work is embodied (as in, "I own a CD of that song," "I own a paperback copy of that book," or "I own a copy of that poem tattooed on my back.") Of course, it would be pretty hard -- and painful -- to sell the tattooed copy of the poem by ripping the skin off of your back!