Can a monoalphabetic substitution cipher attain perfect secrecy?
Definition of perfect secrecy:
$${\rm Pr}[\,{\rm Enc}_k(m_1) = c\,] = {\rm Pr}[\,{\rm Enc}_k(m_2) = c\,]$$
Can a monoalphabetic substitution cipher attain perfect secrecy?
Definition of perfect secrecy:
$${\rm Pr}[\,{\rm Enc}_k(m_1) = c\,] = {\rm Pr}[\,{\rm Enc}_k(m_2) = c\,]$$
Since this is homework, let me just give you a hint: consider the two-character messages $m_1 = \text{"aa"}$ and $m_2 = \text{"ab"}$.
Given a ciphertext $c$ encrypted with a monoalphabetic substitution cipher, can you tell which of $m_1$ or $m_2$ it corresponds to, even without knowing the key? Why (not)? What does this imply about perfect secrecy?
Ps. The hint I gave above assumes that the cipher is not homophonic, i.e. that the encryption of each character is deterministic and independent of its position or the presence of other characters in the message. For a (possibly) homophonic monoalphabetic cipher, it may be simpler to start the argument from the other end: if you intercept the ciphertext $c = \text{"xx"}$, what can you say about the plaintext?
I'm still learning all kinds of ciphers and encryption, but these are my thoughts on the matter.
Mono-alphabhetic substitution cipher fails because it's prone to frequency analysis i.e the probability that the most frequent character in a message could be 'e' is extremely high (a statistic that 'e' is the most frequent letter in a sentence). Therefore, to make mono-alphabhetic substitution cipher invulnerable to frequency analysis attacks, you should probably only refrain to using a single letter once.
So if you're using just the English alphabets (a, b, c, d, e... z), you're pretty much limited to a max 26 length messages such that you use each character only once.
This is just a way of enforcing OTP or Vernam cipher to the English alphabets i.e since in this arrangement, I've forced that encryption of a letter in the message to be independent of the other letters in the word, perfect secrecy is enforced.