Lecture 2: Classical Encryption Techniques

Lecture Notes on Computer and Network Security

by Avi Kak (kak@purdue.edu)
April 19, 2015
10:58am
c
2015
Avinash Kak, Purdue University

Goals:
To introduce the rudiments of encryption/decryption vocabulary.
To trace the history of some early approaches to cryptography
and to show through this history a common failing of humans to
get carried away by the technological and scientific hubris of the
moment.
Python scripts that give you pretty good security for confidential
communications. Only good for fun, though.
1

CONTENTS
Section Title

Page

2.1

Basic Vocabulary of Encryption and Decryption

2.2

Building Blocks of Classical Encryption Techniques

2.3

Caesar Cipher

2.4

The Swahili Angle ...

11

2.5

Monoalphabetic Ciphers

13

2.5.1
2.6
2.6.1
2.7

A Very Large Key Space But ....

15

The All-Fearsome Statistical Attack

16

Comparing the Statistics for Digrams and Trigrams

Multiple-Character Encryption to Mask Plaintext Structure:
The Playfair Cipher

18
20

2.7.1

Constructing the Matrix for Pairwise Substitutions

in the Playfair Cipher

21

2.7.2

Substitution Rules for Pairs of Characters in the

Playfair Cipher

22

2.7.3

Dealing with Duplicate Letters in a Key and Repeating

Letters in Plaintext

24

2.7.4

How Secure Is the Playfair Cipher?

25

2.8

Another Multi-Letter Cipher: The Hill Cipher

2.8.1

2.9

How Secure Is the Hill Cipher?

Polyalphabetic Ciphers: The Vigenere Cipher

2.9.1

How Secure Is the Vigenere Cipher?

28
30
31
32

2.10

Transposition Techniques

34

2.11

Establishing Secure Communications for Fun (But Not for

Profit)

37

2.12

Homework Problems

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Lecture 2

2.1: BASIC VOCABULARY OF

ENCRYPTION AND DECRYPTION

plaintext: This is what you want to encrypt

ciphertext: The encrypted output
enciphering or encryption: The process by which plaintext is
converted into ciphertext
encryption algorithm: The sequence of data processing steps that
go into transforming plaintext into ciphertext. Various parameters used by an encryption algorithm are derived from a secret
key. In cryptography for commercial and other civilian applications, the encryption and decryption algorithms are made public.
secret key: A secret key is used to set some or all of the various
parameters used by the encryption algorithm. The important thing to note is that, in classical cryptography,
the same secret key is used for encryption and decryption. It is for this reason that classical cryptography is
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also referred to as symmetric key cryptography. On the other

hand, in the more modern cryptographic algorithms,
the encryption and decryption keys are not only different, but also one of them is placed in the public
domain. Such algorithms are commonly referred to as asymmetric key cryptography, public key cryptography, etc.
deciphering or decryption: Recovering plaintext from ciphertext
decryption algorithm: The sequence of data processing steps that
go into transforming ciphertext back into plaintext. In classical
cryptography, the various parameters used by a decryption algorithm are derived from the same secret key that was used in the
encryption algorithm.
cryptography: The many schemes available today for encryption
and decryption
cryptographic system: Any single scheme for encryption and decryption
cipher: A cipher means the same thing as a cryptographic system

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Lecture 2

block cipher: A block cipher processes a block of input data at a

time and produces a ciphertext block of the same size.
stream cipher: A stream cipher encrypts data on the fly, usually
one byte at at time.
cryptanalysis: Means breaking the code. Cryptanalysis relies
on a knowledge of the encryption algorithm (that for civilian
applications should be in the public domain) and some knowledge
of the possible structure of the plaintext (such as the structure
of a typical inter-bank financial transaction) for a partial or full
reconstruction of the plaintext from ciphertext. Additionally, the
goal is to also infer the key for decryption of future messages.
The precise methods used for cryptanalysis depend on whether
the attacker has just a piece of ciphertext, or pairs of plaintext
and ciphertext, how much structure is possessed by the plaintext,
and how much of that structure is known to the attacker.
All forms of cryptanalysis for classical encryption exploit the fact
that some aspect of the structure of plaintext may survive in the
ciphertext.
key space: The total number of all possible keys that can be used
in a cryptographic system. For example, DES uses a 56-bit key.
So the key space is of size 256, which is approximately the same
as 7.2 1016.
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brute-force attack: When encryption and decryption algorithms

are publicly available, as they generally are, a brute-force attack
means trying every possible key on a piece of ciphertext until an
intelligible translation into plaintext is obtained.
codebook attack: The attacker tries to acquire as many as possible of the mappings between the plaintext words and the corresponding ciphertext words. In some cases, such a table, referred
to as the codebook, can be used to speed up the brute-force search
for the encryption key. As a trivial example, consider an 8-bit
block cipher. If we can construct a codebook with 256 rows in it,
that would break the cipher.
algebraic attack: You express the plaintext-to-ciphertext relationship as a system of equations. Given a set of (plaintext, ciphertext) pairs, you try to solve the equations for the encryption key.
As you will see, encryption algorithms involve nonlinearities. In
algebraic attacks, one attempts to introduce additional variables
into the system of equations and make nonlinear equations look
linear.
time-memory tradeoff in attacking ciphers: The brute-force
and the codebook attacks represent two opposite cases in terms
of time versus memory needs of the algorithms. Pure brute-force
attacks have very little memory needs, but can require inordinately long times to scan through all possible keys. On the other
hand, codebook attacks can in principle yield results instanta6

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neously, but their memory needs can be humongously large. Just

imagine a codebook for a 64-bit block cipher; it may need as
many as 264 rows in it. In some cases, by trading off memory
for time, it is possible to devise more effective attacks that are
sometimes referred to as time-memory tradeoff attacks. [As a specific
example of time-memory tradeoff, we may be able to reduce the time taken by a brute-force attack if we use
memory to store intermediate results obtained from the current computational steps (assuming they can help
us avoid unnecessary search later during the computations). You will see examples of such tradeoffs in Lecture

24 when we talk about password cracking with rainbow tables.

cryptology: Cryptography and cryptanalysis together constitute

the area of cryptology

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Lecture 2

2.2: BUILDING BLOCKS OF CLASSICAL

ENCRYPTION TECHNIQUES

Two building blocks of all classical encryption techniques are

substitution and transposition.

Substitution means replacing an element of the plaintext with an

element of ciphertext.

Transposition means rearranging the order of appearance of the

elements of the plaintext.

Transposition is also referred to as permutation.

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Lecture 2

2.3: CAESAR CIPHER

This is the earliest known example of a substitution cipher.

Each character of a message is replaced by a character three position down in the alphabet.
plaintext:

are you ready

ciphertext:

DUH BRX UHDGB

If we represent each letter of the alphabet by an integer that

corresponds to its position in the alphabet, the formula for replacing each character p of the plaintext with a character c of the
ciphertext can be expressed as
c = E(3, p) = (p + 3) mod 26
where E() stands for encryption. If you are not already familiar
with modulo division, the mod operator returns the integer remainder of the division when p + 3 is divided by 26, the number
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Lecture 2

of letters in the English alphabet. We are obviously assuming

case-insensitive encoding with the Caesar cipher.
A more general version of this cipher that allows for any degree
of shift would be expressed by
c = E(k, p) = (p + k) mod 26

The formula for decryption would be

p = D(k, c) = (c k) mod 26

In these formulas, k would be the secret key. As mentioned earlier, E() stands for encryption. By the same token, D() stands
for decryption.

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Lecture 2

2.4: THE SWAHILI ANGLE ...

A simple substitution cipher obviously looks much too simple to

be able to provide any security, but that is the case only if you
have some idea regarding the nature of the plaintext.

What if the plaintext could be considered to be a binary stream

of data and a substitution cipher replaced every consecutive 6
bits with one of 64 possible cipher characters? In fact, this is
referred to as Base64 encoding for sending email multimedia
attachments.
[Did you know that all internet communications are character
based? What does that mean and why do you think that is the case? What if you
wanted to send a digital photo over the internet and one of the pixels in the photo
had its graylevel value as 10 (hex: 0A)? If you put such a photo file on the wire
without, say, Base64 encoding, why do you think that would cause problems? Imagine
what would happen if you sent such a photo file to a printer without encoding. Visit
http://www.asciitable.com to understand how the characters of the English alphabet
are generally encoded. Visit the Base64 page at Wikipedia to understand why you need
this type of encoding. A Base64 representation is created by carrying out a bit-level
scan of the data and encoding it six bits at a time into a set of printable characters. For
the most commonly used version of Base64, this 64-element set consists of the characters
A-Z, a-z, 0-9, +, and /.]

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If you did not know anything about the underlying plaintext and
it was encrypted by a Base64 sort of an algorithm, it might not
be as trivial a cryptographic system as it might seem. But, of
course, if the word ever got out that your plaintext was in Swahili,
youd be hosed.

Finally, here is more regarding the slogan All internet communications are character based in the red-and-blue note on the
previous page: As you will see in Lecture 16, the internet communications are governed by the TCP/IP protocol. That protocol
itself does not care whether you put on the wire a purely character based file, an audio file, a video file, etc. The protocol would
work equally well with all sorts of files. So, strictly speaking, the
slogan is technically wrong. Nonetheless, the slogan is of great
practical importance because the software that is charged with
the task of making your data file available to the TCP/IP engine
in your computer could corrupt your data if it is not based on
just printable characters.

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Lecture 2

2.5: A SEEMINGLY VERY STRONG

MONOALPHABETIC CIPHER

The Caesar cipher you just saw is an example of a monoalphabetic cipher. Basically, in a monoalphabetic cipher, you have
a substitution rule that gives you a replacement ciphertext letter
for each letter of the alphabet used in the plaintext message.

Lets now consider what one would think would be a very strong
monoalphabetic cipher. We will make our substitution letters a
random permutation of the 26 letters of the alphabet:
plaintext letters:

f .....

substitution letters:

b .....

The encryption key now is the sequence of substitution letters. In

other words, the key in this case is the actual random permutation
of the alphabet used.

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Since there are 26! permutations of the alphabet, we end up with

an extremely large key space. The number 26! is much larger
than 4 1026. Since each permutation constitutes a key, that
means that the monoalphabetic cipher has a key space of size
larger than 4 1026.

Wouldnt such a large key space make this cipher extremely difficult to break? Not really, as we explain next!

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2.5.1: A Very Large Key Space But ....

The very large key space of a monoalphabetic cipher means that

the total number of all possible keys that would need to be guessed
in a pure brute-force attack would be much too large for such an
attack to be feasible. (This key space is 10 orders of magnitude
larger than the size of the key space for DES, the now somewhat
outdated (but still widely used in the form of 3DES, as described
in Lecture 9) NIST standard that is presented in Lecture 3.) [When
you increase the size of a number by a factor of 10, you are increasing the size by one order of magnitude. So
when we say that the keyspace is 10 orders of magnitude larger, that means that the keyspace is larger by a
factor of 1010 . Recall, as mentioned in Section 2.1, the keyspace of DES is 256 since the key size is 56 bits.

And 256 7.2 1016 .

Obviously, this would rule out a brute-force attack. Even if each

key took only a nanosecond to try, it would still take zillions of
years to try out even half the keys.

So this would seem to be the answer to our prayers for an unbreakable code for symmetric encryption.

But it is not! As to why? Read on.

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Lecture 2

2.6: THE ALL-FEARSOME STATISTICAL

ATTACK

If you know the nature of plaintext, any substitution cipher, regardless of the size of the key space, can be broken easily with a
statistical attack.

When the plaintext is plain English, a simple form of statistical

attack consists measuring the frequency distribution for single
characters, for pairs of characters, for triples of characters, and
so on, and comparing those with similar statistics for English.

Figure 1 shows the relative frequencies for the letters of the English alphabet in a sample of English text. Obviously, by comparing this distribution with a histogram for the letters occurring
in a piece of ciphertext, you may be able to establish the true
identities of the ciphertext letters.

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Lecture 2

Figure 1: Relative frequencies of occurrence for the letters

of the alphabet in a sample of English text. (This figure is from
Lecture 2 of Computer and Network Security by Avi Kak)

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Lecture 2

2.6.1: Comparing the Statistics for Digrams and

Trigrams

Equally powerful statistical inferences can be made by comparing

the relative frequencies for pairs and triples of characters in the
ciphertext and the language believed to be used for the plaintext.

Pairs of adjacent characters are referred to as digrams, and

triples of characters as trigrams.

Shown in Table 1 are the digram frequencies. The table does not
include digrams whose relative frequencies are below 0.47. (A
complete table of frequencies for all possible digrams would have
676 entries in it.)

If we have available to us the relative frequencies for all possible digrams, we can represent this table by the joint probability
p(x, y) where x denotes the first letter of a digram and y the
second letter. Such joint probabilities can be used to compare
the digram-based statistics of ciphertext and plaintext.

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The most frequently occurring trigrams ordered by decreasing

frequency are:
the

digram frequency
th
3.15
he
2.51
an
1.72
in
1.69
er
1.54
re
1.48
es
1.45
on
1.45
ea
1.31
ti
1.28
at
1.24
st
1.21
en
1.20
nd
1.18
or
1.13

and

ent

ion

digram frequency
to
1.11
nt
1.10
ed
1.07
is
1.06
ar
1.01
ou
0.96
te
0.94
of
0.94
it
0.88
ha
0.84
se
0.84
et
0.80
al
0.77
ri
0.77
ng
0.75

tio

f or

nde

.....

digram frequency digram frequency

sa
0.75
ma
0.56
hi
0.72
ta
0.56
le
0.72
ce
0.55
so
0.71
ic
0.55
as
0.67
ll
0.55
no
0.65
na
0.54
ne
0.64
ro
0.54
ec
0.64
ot
0.53
io
0.63
tt
0.53
rt
0.63
ve
0.53
co
0.59
ns
0.51
be
0.58
ur
0.49
di
0.57
me
0.48
li
0.57
wh
0.48
ra
0.57
ly
0.47

Table 1: Digram frequencies in English text (This table is from

Lecture 2 of Computer and Network Security by Avi Kak)

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Lecture 2

2.7: MULTIPLE-CHARACTER
ENCRYPTION TO MASK PLAINTEXT
STRUCTURE: THE PLAYFAIR CIPHER

One character at a time substitution obviously leaves too much

of the plaintext structure in ciphertext.

So how about destroying some of that structure by mapping multiple characters at a time to ciphertext characters?

One of the best known approaches in classical encryption that carries out multiple-character substitution is known as the Playfair
cipher, which is described in the next subsection.

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Lecture 2

2.7.1: Constructing the Matrix for Pairwise

Substitutions in Playfair Cipher

In Playfair cipher, you first choose an encryption key. You then

enter the letters of the key in the cells of a 5 5 matrix in a left to
right fashion starting with the first cell at the top-left corner. You
fill the rest of the cells of the matrix with the remaining letters in
alphabetic order. The letters I and J are assigned the same cell. In
the following example, the key is smythework:

I/J

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Lecture 2

2.7.2: Substitution Rules for Pairs of Characters in

Playfair Cipher

1. Two plaintext letters that fall in the same row of the 5 5 matrix are replaced by letters to the right of each in the row. The
rightness property is to be interpreted circularly in each row,
meaning that the first entry in each row is to the right of the
last entry. Therefore, the pair of letters bf in plaintext will get
replaced by CA in ciphertext.

2. Two plaintext letters that fall in the same column are replaced
by the letters just below them in the column. The belowness
property is to be considered circular, in the sense that the topmost
entry in a column is below the bottom-most entry. Therefore, the
pair ol of plaintext will get replaced by CV in ciphertext.

3. Otherwise, for each plaintext letter in a pair, replace it with the

letter that is in the same row but in the column of the other
letter. Consider the pair gf of the plaintext. We have g in
the fourth row and the first column; and f in the third row and
the fifth column. So we replace g by the letter in the same row
as g but in the column that contains f. This given us P as a
replacement for g. And we replace f by the letter in the same
row as f but in the column that contains g. That gives us A
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as replacement for f. Therefore, gf gets replaced by PA.

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2.7.3: Dealing with Duplicate Letters in a Key and

Repeating Letters in Plaintext

You must drop any duplicates in a key.

Before the substitution rules are applied, you must insert a chosen
filler letter (lets say it is x) between any repeating letters in
the plaintext. So a plaintext word such as hurray becomes
hurxray

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Lecture 2

2.7.4: How Secure is the Playfair Cipher?

Playfair was thought to be unbreakable for many decades.

It was used as the encryption system by the British Army in

World War 1. It was also used by the U.S. Army and other
Allied forces in World War 2.

But, as it turned out, Playfair was extremely easy to break.

As expected, the cipher does alter the relative frequencies associated with the individual letters and with digrams and with
trigrams, but not sufficiently.

Figure 2 shows the single-letter relative frequencies in descending

order (and normalized to the relative frequency of the letter e)
for some different ciphers. There is still considerable information
left in the distribution for good guesses.

The cryptanalysis of the Playfair cipher is also aided by the fact

that a digram and its reverse will encrypt in a similar fashion.
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Lecture 2

That is, if AB encrypts to XY, then BA will encrypt to YX.

So by looking for words that begin and end in reversed digrams,
one can try to compare them with plaintext words that are similar. Example of words that begin and end in reversed digrams:
receiver, departed, repairer, redder, denuded, etc.

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Lecture 2

Figure 2: Single-letter relative frequencies in descending

order for a class of ciphers. (This figure is from Chapter 2 of William Stallings:
Cryptography and Network Security, Fourth Edition, Prentice-Hall.)

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Lecture 2

2.8: ANOTHER MULTI-LETTER CIPHER:

THE HILL CIPHER

The Hill cipher takes a very different (more mathematical) approach to multi-letter substitution, as we describe in what follows.

You assign an integer to each letter of the alphabet. For the

sake of discussion, lets say that you have assigned the integers 0
through 25 to the letters a through z of the plaintext.

The encryption key, call it K, consists of a 33 matrix of integers:

k11 k12 k13

k21 k22 k23

k31 k32 k33

Now we can transform three letters at a time from the plaintext, the letters being represented by the numbers p1, p2, and
p3, into three ciphertext letters c1 , c2, and c3 in their numerical
representations by
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c1 = ( k11p1 + k12p2 + k13p3 ) mod 26

c2 = ( k21p1 + k22p2 + k23p3 ) mod 26
c3 = ( k31p1 + k32p2 + k33p3 ) mod 26

The above set of linear equations can be written more compactly

in the following vector-matrix form:
~ = [K] P
~ mod 26
C

Obviously, the decryption would require the inverse of K matrix.

~ =
P

~ mod 26
C

This works because

~ =
P

~ mod 26 = P
~
[K] P

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Lecture 2

2.8.1: How Secure is Hill Cipher?

It is extremely secure against ciphertext only attacks. That is

because the keyspace can be made extremely large by choosing
the matrix elements from a large set of integers. (The key space
can be made even larger by generalizing the technique to larger
matrices.)

But it has zero security when the plaintextciphertext pairs are

known. The key matrix can be calculated easily from a set of
~ C
~ pairs.
known P,

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Lecture 2

2.9: POLYALPHABETIC CIPHERS: THE

VIGENERE CIPHER

In a monoalphabetic cipher, the same substitution rule is used

at every character position in the plaintext message. In a polyalphabetic cipher, on the other hand, the substitution rule changes
continuously from one character position to the next in the plaintext according to the elements of the encryption key.

In the Vigenere cipher, you first align the encryption key with
the plaintext message. [If the plaintext message is longer than the encryption
key, you can repeat the encryption key, as we show below where the encryption key
is abracadabra.]

Now consider each letter of the encryption key

denoting a shifted Caesar cipher, the shift corresponding to the
letter of the key. This is illustrated with the help of the table
shown on the next page.

Now a plaintext message may be encrypted as shown below:

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key:
plaintext:
ciphertext:

Lecture 2

abracadabraabracadabraabracadabraab
canyoumeetmeatmidnightihavethegoods
CBEYQUPEFKMEBK.....................

The Vigenere cipher is an example of a polyalphabetic cipher.

Since, in general, the encryption key will be shorter than the message to be encrypted, for the Vigenere cipher the key is repeated,
as mentioned previously and as illustrated in the above example
where the key is the string abracadabra.
encryption key
plain text letters
letter
a b c d ............
substitution letters
a
A B C D ............
b
B C D E ............
c
C D E F ............
d
D E F G ............
e
E F G H ............
.
. . . .
.
.
. . . .
.
z
Z A B C ............

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Lecture 2

2.9.1: How Secure is the Vigenere Cipher?

Since there exist in the output multiple ciphertext letters for each
plaintext letter, you would expect that the relative frequency distribution would be effectively destroyed. But as can be seen in
the plots in Figure 2, a great deal of the input statistical distribution still shows up in the output. [The plot shown for Vigenere cipher is for an
encryption key that is just 9 letters long.]

Obviously, the longer the encryption key, the greater the masking
of the structure of the plaintext. The best possible key is as long
as the plaintext message and consists of a purely random permutation of the 26 letters of the alphabet. This would yield the
ideal plot shown in Figure 2. The ideal plot is labeled Random
polyalphabetic in that figure.

In general, to break the Vigenere cipher, you first try to estimate

the length of the encryption key. This length can be estimated
by using the logic that plaintext words separated by multiples of
the length of the key will get encoded in the same way.

If the estimated length of the key is N, then the cipher consists of

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N monoalphabetic substitution ciphers and the plaintext letters

at positions 1, N, 2N, 3N, etc., will be encoded by the same
monoalphabetic cipher. This insight can be useful in the decoding
of the monoalphabetic ciphers involved.

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Lecture 2

2.10: TRANSPOSITION TECHNIQUES

All of our discussion so far has dealt with substitution ciphers. We

have talked about monoalphabetic substitutions, polyalphabetic
substitutions, etc.

We will now talk about a different notion in classical cryptography: permuting the plaintext.
This is how a pure permutation cipher could work: You write
your plaintext message along the rows of a matrix of some size.
You generate ciphertext by reading along the columns. The order
in which you read the columns is determined by the encryption
key:
key:

4 1 3 6 2 5

plaintext:

m
a
i
r
d

e
t
g
t
i
35

e
m
h
h
e

t
i
t
e
s

m
d
f
g
x

e
n
o
o
y

Computer and Network Security by Avi Kak

ciphertext:

Lecture 2

ETGTIMDFGXEMHHEMAIRDENOOYTITES

The cipher can be made more secure by performing multiple

rounds of such permutations.

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Lecture 2

2.11: Establishing Secure Communications

for Fun (But Not for Profit)

If your goal is to establish a medium-strength secure communication link, you may be able to get by without having to resort to
the full-strength crypto systems that we will be studying in later
lectures.

This section presents two scripts, EncryptForFun.py and DecryptForFun.py,

that you can use to create secure communication links with your
friends and relatives. Fundamentally, the encryption/decryption
logic in these scripts is based on the following properties of XOR
operations on bit blocks. Assuming that A, B, and C are bit
arrays, we can write
[A B] C
A A
A 0

=
=
=

A [B C
0
A

More precisely, the encryption script shown below is based on

differential XORing of bit blocks. The document to be encrypted
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Lecture 2

is scanned in bit blocks of size BLOCKSIZE. Let the bit blocks be

denoted B0, B1, B2, . . .. After it is XORed with the key, the very
first bit block, B0, is XORed with an initialization vector (IV )
that is derived from a pass-phrase. The output of this operation
is XORed with the key-XORed B1, and so on.

Differential XORing destroys any repetitive patterns in the messages to be encrypted and makes it more difficult to break encryption by statistical analysis. Differential XORing needs an
Initialization Vector that, as already mentioned, is derived from
a pass phrase in the script shown below.

The implementation shown below is made fairly compact by the

use of the BitVector module. [This would be a good time to become
familiar with the BitVector module by going through its API. Youll be using
this module in several homework assignments dealing with cryptography and
hashing.]

#!/usr/bin/env python
###
###
###

EncryptForFun.py
Avi Kak (kak@purdue.edu)
January 21, 2014

###
###

Medium strength encryption/decryption for secure

message exchange for fun.

###
###

Call syntax:

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Computer and Network Security by Avi Kak

###
###
###

EncryptForFun.py

Lecture 2

message_file.txt

output.txt

The encrypted output is deposited in the file output.txt

PassPhrase = "Hopes and dreams of a million years"

import sys
from BitVector import *

#(A)

if len(sys.argv) is not 3:
sys.exit(Needs two command-line arguments, one for
the message file and the other for the
encrypted output file)

#(B)

BLOCKSIZE = 64
numbytes = BLOCKSIZE / 8

#(C)
#(D)

# Reduce the passphrase to a bit array of size BLOCKSIZE:

bv_iv = BitVector(bitlist = [0]*BLOCKSIZE)
for i in range(0,len(PassPhrase) / numbytes):
textstr = PassPhrase[i*numbytes:(i+1)*numbytes]
bv_iv ^= BitVector( textstring = textstr )

#(E)
#(F)
#(G)
#(H)

# Get key from user:

try:
key = raw_input("Enter key: ")
except EOFError: sys.exit()
if len(key) < numbytes:
key = key + 0 * (numbytes-len(key))

#(I)
#(J)
#(K)
#(L)
#(M)

# Reduce the key to a bit array of size BLOCKSIZE:

key_bv = BitVector(bitlist = [0]*BLOCKSIZE)
for i in range(0,len(key) / numbytes):
keyblock = key[i*numbytes:(i+1)*numbytes]
key_bv ^= BitVector( textstring = keyblock )

#(N)
#(O)
#(P)
#(Q)

# Create a bitvector for storing the ciphertext bit array:

msg_encrypted_bv = BitVector( size = 0 )

#(R)

# Carry out differential XORing of bit blocks and encryption:

previous_block = bv_iv
bv = BitVector( filename = sys.argv[1] )
while (bv.more_to_read):

#(S)
#(T)
#(U)

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Lecture 2

bv_read = bv.read_bits_from_file(BLOCKSIZE)
if len(bv_read) < BLOCKSIZE:
bv_read += BitVector(size = (BLOCKSIZE - len(bv_read)))
bv_read ^= key_bv
bv_read ^= previous_block
previous_block = bv_read.deep_copy()
msg_encrypted_bv += bv_read
outputhex = msg_encrypted_bv.getHexStringFromBitVector()

#(V)
#(W)
#(X)
#(Y)
#(Z)
#(a)
#(b)
#(c)

# Write ciphertext bitvector to the ouput file:

FILEOUT = open(sys.argv[2], w)
FILEOUT.write(outputhex)
FILEOUT.close()

#(d)
#(e)
#(f)

In the script shown above, if the size (in terms of the number of
bits) of the message file is not an integral multiple of BLOCKSIZE,
the script appends a sequence of null bytes (that is, bytes made
up of all zeros) at the end so that this condition is satisfied. This
is done in line (W) and (X) of the script.

The decryption script, shown below, uses the same properties of

the XOR operator as stated at the beginning of this section to
recover the original message from the encrypted output.

The reader may wish to compare the decryption logic in the loop
in lines (U) through (b) of the script shown below with the encryption logic shown in lines (S) through (b) of the script above.

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Computer and Network Security by Avi Kak

Lecture 2

#!/usr/bin/env python
###
###
###

DecryptForFun.py
Avi Kak (kak@purdue.edu)
January 21, 2014

###
###

Medium strength encryption/decryption for secure

message exchange for fun.

###
###
###
###
###

Call syntax:
DecryptForFun.py

encrypted_file.txt

recover.txt

The decrypted output is deposited in the file recover.txt

PassPhrase = "Hopes and dreams of a million years"

import sys
from BitVector import *

#(A)

if len(sys.argv) is not 3:
sys.exit(Needs two command-line arguments, one for
the encrypted file and the other for the
decrypted output file)

#(B)

BLOCKSIZE = 64
numbytes = BLOCKSIZE / 8

#(C)
#(D)

# Reduce the passphrase to a bit array of size BLOCKSIZE:

bv_iv = BitVector(bitlist = [0]*BLOCKSIZE)
for i in range(0,len(PassPhrase) / numbytes):
textstr = PassPhrase[i*numbytes:(i+1)*numbytes]
bv_iv ^= BitVector( textstring = textstr )

#(E)
#(F)
#(G)
#(H)

# Create a bitvector from the ciphertext hex string:

FILEIN = open(sys.argv[1])
encrypted_bv = BitVector( hexstring = FILEIN.read() )

#(I)
#(J)

# Get key from user:

try:
key = raw_input("Enter key: ")
except EOFError: sys.exit()
if len(key) < numbytes:
key = key + 0 * (numbytes-len(key))

#(K)
#(L)
#(M)
#(N)
#(O)

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Lecture 2

# Reduce the key to a bit array of size BLOCKSIZE:

key_bv = BitVector(bitlist = [0]*BLOCKSIZE)
for i in range(0,len(key) / numbytes):
keyblock = key[i*numbytes:(i+1)*numbytes]
key_bv ^= BitVector( textstring = keyblock )

#(P)
#(Q)
#(R)
#(S)

# Create a bitvector for storing the output plaintext bit array:

msg_decrypted_bv = BitVector( size = 0 )
#(T)
# Carry out differential XORing of bit blocks and decryption:
previous_decrypted_block = bv_iv
for i in range(0, len(encrypted_bv) / BLOCKSIZE):
bv = encrypted_bv[i*BLOCKSIZE:(i+1)*BLOCKSIZE]
temp = bv.deep_copy()
bv ^= previous_decrypted_block
previous_decrypted_block = temp
bv ^= key_bv
msg_decrypted_bv += bv

#(U)
#(V)
#(W)
#(X)
#(Y)
#(Z)
#(a)
#(b)

outputtext = msg_decrypted_bv.getTextFromBitVector()

#(c)

# Write the plaintext to the output file:

FILEOUT = open(sys.argv[2], w)
FILEOUT.write(outputtext)
FILEOUT.close()

#(d)
#(e)
#(f)

To exercise these scripts, enter some text in a file and lets call
this file message.txt. Now you can call the encrypt script by
EncryptForFun.py

message.txt

output.txt

The script will place the encrypted output, in the form of a hex
string, in the file output.txt. Subsequently, you can call
DecryptForFun.py

output.txt

recover.txt

to recover the original message from the encrypted output produced by the first script.
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Lecture 2

The security level of this script can be taken to full strength by

using 3DES or AES for encrypting the bit blocks produced by
differential XORing.

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Lecture 2

2.12: HOMEWORK PROBLEMS

1. Use the ASCII codes available at http://www.asciitable.com to manually construct a Base64 encoded version of the string hello\njello.
Your answer should be aGVsbG8KamVsbG8=. What do you think the
character = at the end of the Base64 representation is for? [If
you wish you can also use interactive Python for this. Enter the following sequence of commands import
base64 followed by base64.b64encode(hello\njello). If you are using Python 3, make sure you
prefix the argument to the b64encode() function by the character b to indicate that it is of type bytes as
opposed to of type str. Several string processing functions in Python 3 require bytes type arguments and
often return results of the same type. Educate yourself on the difference between the string str type and bytes

type in Python 3.

2. A text file named myfile.txt that you created with a run-ofthe-mill editor contains just the following word:
hello
If you examine this file with a command like
hexdump

-C

myfile.txt

you are likely to see the following bytes (in hex) in the file:
68

65

6C

6C

6F

0A
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Computer and Network Security by Avi Kak

Lecture 2

which translate into the following bit content:

01101000 01100101 01101100 01101100 01101111 00001010

Looks like there are six bytes in the file whereas the word hello
has only five characters. What do you think is going on? Do you
know why your editor might want to place that extra byte in the
file and how to prevent that from happening?
3. All classical ciphers are based on symmetric key encryption. What
does that mean?
4. What are the two building blocks of all classical ciphers?
5. True or false: The larger the size of the key space, the more secure
a cipher? Justify your answer.
6. Give an example of a cipher that has an extremely large key space
size, an extremely simple encryption algorithm, and extremely
poor security.
7. What is the difference between monoalphabetic substitution ciphers and polyalphabetic substitution ciphers?
8. What is the main security flaw in the Hill cipher?
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Computer and Network Security by Avi Kak

Lecture 2

9. What makes Vigenere cipher more secure than, say, the Playfair
cipher?

10. Programming Assignment:

Write a script called hist.pl in Perl (or hist.py in Python)
that makes a histogram of the letter frequencies in a text file.
The output should look like
A: xx
B: xx
C: xx
...
...
where xx stands for the count for that letter.

11. Programming Assignment:

Write a script called poly_cipher.pl in Perl (or poly_cipher.py
in Python) that is an implementation of the Vigenere polyalphabetic cipher for messages composed from the letters of the English
alphabet, the numerals 0 through 9, and the punctuation marks
., ,, and ?.
Your script should read from standard input and write to standard output. It should prompt the user for the encryption key.
Your hardcopy submission for this homework should include some
sample plaintext, the ciphertext, and the encryption key used.
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Computer and Network Security by Avi Kak

Lecture 2

Make your scripts as compact and as efficient as possible. Make

liberal use of builtin functions for what needs to be done. For
example, you could make a circular list with either of the following
two constructs in Perl:
unshift( @array, pop(@array) )
push( @array, shift(@array) )
See perlfaq4 for some tips on array processing in Perl.

12. Programming Assignment:

This is an exercise in you assuming the role of a cryptanalyst and
trying to break a cryptographic system that consists of the two
Python scripts you saw in Section 2.11. As youll recall, the script
EncryptForFun.py can be used for encrypting a message file and
the script DecryptForFun.py for recovering the plaintext message
from the ciphertext created by the first script. You can download
both these scripts in the code archive for Lecture 2.
With BLOCKSIZE set to 16, the script EncryptForFun.py produces
the following ciphertext output for a plaintext message that is a
quote by Mark Twain:
20352a7e36703a6930767f7276397e376528632d6b6665656f6f6424623c2d\
30272f3c2d3d2172396933742c7e233f687d2e32083c11385a03460d440c25

all in one line. (You can copy-and-paste this hex ciphertext into
your own script. However, make sure that you delete the backslash at the end of the first line. You can also see the same
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Computer and Network Security by Avi Kak

Lecture 2

output in the file named output5.txt in the code archive for Lecture 2.) Your job is to both recover the original quote and the
encryption key used by mounting a brute-force attack on the encryption/decryption algorithms. (HINT: The logic used in the
scripts implies that the effective key size is only 16 bits when the
BLOCKSIZE variable is set to 16. So your brute-force attack need
search through a keyspace of size only 216.)

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Computer and Network Security by Avi Kak

Lecture 2

CREDITS

The data presented in Figure 1 and Table 1 are from http://

jnicholl.org/Cryptanalysis/Data/EnglishData.php. That
site also shows a complete digram table for all 676 pairings of the
letters of the English alphabet.

49