Problem Set _ 3

Problem Set _ 3 - Chemistry
2311
...

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Unformatted text preview: Chemistry
2311
 Homework
Problems‐
Chapter
3
 Section
I:


 (a) Which
of
the
following
represents
(1)
an
elimination
reaction,
(2)
a
substitution
 reaction,
(3)
an
addition
reaction,
and
(4)
a
rearrangement?
 
 
 
 
 
 ( b ) T h e 
 p K a
 f o r 
 t h e 
 i o n i z a t i o n 
 o f 
 a c e t i c 
 a c i d 
 i n 
 w a t e r 
 i s 
 4 . 7 5 . 
 
 W h i c h 
 o f 
 t h e 
 f o l l o w i n g 
 v a l u e s 
 i s 
 t h e 
 c o r r e s p o n d i n g 
 K a? 
 ( 1 ) 4 . 6 3 
 x 
 1 0 ‐5 
 
 
 
 
 
 
 
 
 
 ( 2 ) 
 4 . 6 3 
 x 
 1 0 ‐4 
 
 
 
 
 
 
 
 
 
 ( 3 ) 
 1 . 7 6 
 x 
 1 0 ‐5 
 
 
 
 
 
 
 
 
 
 ( 4 ) 
 1 . 7 6 
 x 
 1 0 ‐4 
 
 (c) For
which
of
the
following
reactions
would
you
expect
a
positive
(+)
entropy
of
 reaction?
 
 
 
 
 
 
 
 
 
 ( d ) W h i c h 
 o f 
 t h e 
 f o l l o w i n g 
 m o l e c u l e s 
 h a s 
 t h e 
 l a r g e s t 
 p K a? 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 















 
 S e c t io n 
II:

In d ic a t e 
T r u e 
( T ) 
o r 
F a ls e 
( F ) 
f o r 
e a c h 
o f 
t h e 
f o llo w in g 
s t a t e m e n t s :
 ( a ) A c c o r d in g 
t o 
B r o n s t e d ‐ L o w r y ,
a n 
a c id 
is 
a 
s u b s t a n c e 
t h a t 
c a n 
d o n a t e 
a 
p r o t o n 
a n d 
a 
b a s e 
is 
a 
 s u b s t a n c e 
t h a t 
c a n 
a c c e p t 
a 
p r o t o n .
 ( b ) A c c o r d in g 
t o 
L e w is ,
a n 
a c id 
is 
a n 
e le c t r o n 
p a ir 
d o n o r 
a n d 
a 
b a s e 
is 
a n 
e le c t r o n 
p a ir 
a c c e p t o r .
 ( c ) C a r b o c a t io n s 
a r e 
L e w is 
a c id s .
 ( d ) C a r b a n io n s 
a r e 
e le c t r o n 
d e f ic ie n t 
e le c t r o p h ilic 
s p e c ie s .
 ( e ) T h e 
la r g e r 
t h e 
v a lu e 
o f 
t h e 
p K a ,
t h e 
w e a k e r 
t h e 
a c id .
 ( f ) T h e 
w e a k e r 
t h e 
a c id ,
t h e 
s t r o n g e r 
t h e 
c o n ju g a t e 
b a s e .
 ( g ) H I
is 
a 
s t r o n g e r 
a c id 
t h a n 
H C l.
 ( h ) W a t e r 
is 
a 
s t r o n g e r 
a c id 
t h a n 
a m m o n ia .
 ( i ) A 
 h y d r o g e n 
 a t t a c h e d 
 t o 
 a n 
 s p 
 c a r b o n 
 i s 
 m o r e 
 a c i d i c 
 t h a n 
 a 
 h y d r o g e n 
 a t t a c h e d 
 t o 
 a n 
 s p 2
 c a r b o n . 
 ( j) A 
c h lo r o 
s u b s t it u e n t 
a t t a c h e d 
t o 
c a r b o n 
e x h ib it s 
a n 
e le c t r o n 
w it h d r a w in g 
in d u c t iv e 
e f f e c t .
 ( k ) E x o t h e r m ic 
r e a c t io n s 
h a v e 
a 
p o s it iv e 
( + ) 
e n t h a lp y 
o f 
r e a c t io n .
 ( l ) A 
 n e g a t i v e 
 v a l u e 
 o f 
 Δ G o
 i s 
 a s s o c i a t e d 
 w i t h 
 r e a c t i o n s 
 t h a t 
 f a v o r 
 t h e 
 f o r m a t i o n 
 o f 
 p r o d u c t s 
 w h e n 
 e q u ilib r iu m 
is 
r e a c h e d .
 ( m ) A 
p o s it iv e 
e n t r o p y 
c h a n g e 
m a k e s 
a 
n e g a t iv e 
c o n t r ib u t io n 
t o 
t h e 
c h a n g e 
in 
f r e e 
e n e r g y 
a n d 
is 
 e n e r g e t ic a lly 
f a v o r a b le 
f o r 
t h e 
f o r m a t io n 
o f 
p r o d u c t s .
 ( n ) A 
p r o t ic 
s o lv e n t 
is 
o n e 
t h a t 
h a s 
a 
h y d r o g e n 
a t o m 
a t t a c h e d 
t o 
a 
s t r o n g ly 
e le c t r o p o s it iv e 
e le m e n t 
 s u c h 
a s 
o x y g e n 
a n d 
n it r o g e n .
 S e c t io n 
III:
 ( a ) C o m p le t e 
e a c h 
o f 
t h e 
f o llo w in g 
r e a c t io n s .
 
 
 
 
 
 
 
 
 
 
 ( b ) D e s ig n a t e 
t h e 
L e w is 
a c id 
a n d 
L e w is 
b a s e 
in 
e a c h 
o f 
t h e 
f o llo w in g 
r e a c t io n s .
 
 
 
 
 
 ( c ) R e w r it e 
t h e 
f o llo w in g 
r e a c t io n 
u s in g 
c u r v e d 
a r r o w s 
a n d 
s h o w 
a ll
n o n b o n d in g 
e le c t r o n 
p a ir s .
 
 
 ...
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