Introduction to Bioorganic Chemistry and Chemical Biology
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.
1000 monkeys
×
1000 years
×
monkey
365 days
1 year
×
24 hours
day
×
60 minutes
1080 characters
×
hour
minute
= 5.7 × 1014 characters
Introduction to Bioorganic Chemistry and Chemical Biology | A1045
Van Vranken & Weiss | 978-0-8153-4214-4
Arguably,
the shortest possible work of William Shakespeare
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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 × 1020 ways to combine 26 English letters, a space, and a
period—a vast number that creates insurmountable odds for the poor monkeys. If we
scanned each monkey’s string of characters from beginning to end, the entire set could
contain no more than 5.7 × 1014 14-character combinations, so that, even with our
optimistic assumptions, the odds are a million to one against the monkeys.
Answer 1.2
A
2610 = 1.41167096 × 1014
B
41000 = 1.60693804 × 10600
C
4100 = 1.60693804 × 1060
D
20100 = 1.26765060 × 10130
Answer 1.3
A DNA strand with 27 subunits has a potential diversity of 427 = 1.8 × 1016.
Answer 1.4
cross-conjugated
cross-conjugated
N
-O
O
N
O
O
N
-O
O
+
O
O-
N
O-
-O
O
+
O-
Introduction to Bioorganic Chemistry and Chemical Biology | A1046
Van Vranken & Weiss | 978-0-8153-4214-4
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note:
10 e- = aromatic
1
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 membrane).
C
Three (plasma membrane plus outer mitochondrial membrane plus inner mitochondrial membrane).
*Answer 1.8
Li
O
Ph
O
OLi
EtCOCl
2
4
3
x
x
aldehydes
alkyllithiums acid chlorides
Et
O
Ph
ester
Ph
=
24
esters
Introduction to Bioorganic Chemistry and Chemical Biology | A1047
Van Vranken & Weiss | 978-0-8153-4214-4
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