Introduction to Bioorganic Chemistry and Chemical Biology 1

Answers to Chapter 1
(in-text & asterisked problems)
Answer 1.1
No. This question is designed to assess whether you can locate simple information,
make reasonable assumptions, and then apply it to a problem. We did not specify the
productivity of the monkeys in question. We did not specify whether their productivity
would decline as they aged. We did not even specify which work of Shakespeare. The
important point is that even if you make the most optimistic assumptions, the answer
to the question is no.
A thousand monkeys, each typing at the fastest recorded human speed of 1080 characters
per minute for a thousand years, would type over a hundred trillion characters.
Arguably, the shortest possible work of William Shakespeare would be his abbreviated
name (for example W. Shakespeare), a mere 14 English letters, a space, and a period.
However, there are over 1.8 10
20
ways to combine 26 English letters, a space, and a
perioda vast number that creates insurmountable odds for the poor monkeys. If we
scanned each monkeys string of characters from beginning to end, the entire set could
contain no more than 5.7 10
14
14-character combinations, so that, even with our
optimistic assumptions, the odds are a million to one against the monkeys.
Answer 1.2
A 26
10
=1.41167096 10
14
B 4
1000
=1.60693804 10
600
C 4
100
=1.60693804 10
60
D 20
100
=1.26765060 10
130
Answer 1.3
A DNA strand with 27 subunits has a potential diversity of 4
27
= 1.8 10
16
.
Answer 1.4
Introduction to Bioorganic Chemistry and Chemical Biology | A1045
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monkey
1000 years 1000 monkeys
= 5.7 10
14
characters

1 year
365 days

day
24 hours
hour
60 minutes

minute
1080 characters

Introduction to Bioorganic Chemistry and Chemical Biology | A1046
Van Vranken & Weiss | 978-0-8153-4214-4
www.garlandscience.com design by www.blink.biz
O O - O
N
O
+
- O O -
N
O
+
O - - O
N
O - O O
N
cross-conjugated cross-conjugated
note:
10 e
-
= aromatic
2 Introduction to Bioorganic Chemistry and Chemical Biology: ANSWERS TO CHAPTER 1
*Answer 1.6
A Two (outer membrane plus inner membrane).
B Three (plasma membrane plus outer nuclear membrane plus inner nuclear mem-
brane).
C Three (plasma membrane plus outer mitochondrial membrane plus inner mito-
chondrial membrane).
*Answer 1.8
Introduction to Bioorganic Chemistry and Chemical Biology | A1047
Van Vranken & Weiss | 978-0-8153-4214-4
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ester
Li
O
Ph
OLi
Ph
EtCOCl
O
Ph
Et
O
2
x
4 3
x
=
24
aldehydes alkyllithiums acid chlorides esters