Cryptography is the art of secret writing, and cryptanalysis is the art of breaking ciphers. Data Encryption Standard (DES) is one of the most popular iterative cryptoscheme, but it is very much sensitive to differential cryptanalysis. In this thesis, a new cryptosystem is analysed to compare it with DES. First it is compared on the basis of the resistivity to differential cryptanalysis and then to observe its resistivity to other cryptanalysis schemes, we proceed to implement several randomness tests and apply these tests on both cryptosystems (DES and the new cryptosystem). We also implement an automated password generator using DES which produces random yet pronounceable passwords. Our studies reveal that the new cryptosystem is superior to the DES against differential cryptanalysis scheme and, for small number of rounds, produces more random output, which makes it more difficult to analyse with respect to other cryptanalysis schemes.