CHM 201 Organic Chemistry 1 Practice Problems KEY

Chapter 03 Introdction to Organic !eaction and Mechanism "#cid$%ase&

1. Which of the following is not a conjugate acid - conjugate base pair (in that order)?
a) H3PO! H"PO

b) H#$! #$

c) %H3%H"OH! %H3%H"O


d) H3O
&
! H"O
e& HPO'

( H2PO'

". What is'are the product(s) of the following acid-base (echanis(?

H
BrMg
a)
+ BrMg H
b&
MgBr
+ CH
3
CH
3
c)
H
d)
MgBr
+ CH
3
CH
3

e) )one of these choices.
3. Which of the following is not a *ewis base?
a) )H3 b) H

c& %)3 d) H"O e) H3%

1
. Which of these is not a *ewis acid?
a) +l#r3 b) #%l3 c& Ph3P

d) ,
&
e) +ll these choices are *ewis acids
-. .n the following reaction which che(ical species is acting li/e a nucleophile?



a) b) c&


d) two of these choices e) there is no nucleophile in this reaction
0. Which of the following organic co(pounds is the strongest acid?
a) %0H1" p1a 2 -" b) %H3%H3 p1a 2 -3 c) %H3%H"OH p1a 2 14

d) %H3%O"H p1a 2 - e& C)3CO2H pKa * 0
5. Which of the following correctl6 lists the co(pounds in order of decreasing acidit6?
a& H2O + HC CH + ,H3 + CH3CH3
b) H%%H 7 H"O 7 )H3 7 %H3%H3
c) %H3%H3 7 H%%H 7 )H3 7 H"O
d) %H3%H3 7 H%%H 7 H"O 7 )H3
e) H"O 7 )H3 7 H%%H 7 %H3%H3
"
4. 8an/ the bold$-aced h6drogens for the following co(pounds fro( (ost acidic to least acidic.


. .. ...
.9 9
H
H
OH
O
H
O
HO
CH
3
H

a) ... 7 .9 7 . 7 9 7 ..
b) .. 7 ... 7 9 7 .9 7 .
c) .. 7 9 7 ... 7 .9 7 .
d) 9 7 ... 7 .. 7 .9 7 .
e& III + I + I. + . + II
:. ;he basic species are arranged in decreasing order of basicit6 in the se<uence=
a) $

7 O%H3

7 )H"

7 %H3%H"

b) O%H3

7 %H3%H"

7 )H"

7 $

c& CH3CH2

+ ,H2

+ OCH3

+ )

d) )H"

7 %H3%H"

7 $

7 O%H3

e) )H"

7

O%H3

7 %H3%H"

7 $

13. Which one of the following is a true state(ent?

a) ;he stronger the acid! the larger is its p1a.
b) ;he conjugate base of a strong acid is a strong base.
c) +cid-base reactions alwa6s fa>or the for(ation of the stronger acid and the stronger base.
d& /trong acids can ha0e negati0e pKa 0ales1
e) H6drogen need not be present in the (olecular for(ula of a #ronsted-*owr6 acid.
11. Which is the strongest acid?
a) %H"%l%H"%H"%H"%H"%O"H
b) %H3%H#r%H"%H"%H"%O"H
c) %H3%H"%H"%#r"%H"%O"H
d) %H3%H"%H"%H$%H"%O"H
3
e& CH3CH2CH2C)2CH2CO2H
1". .n the reaction! )a
&
)H"

& %H3OH %H3O

)a
&
& )H3! the stronger base is=
a& ,a,H2 b) %H3OH c) %H3O)a
d) )H3 e) ;his is not an acid-base reaction.
13. Which of these bases is the strongest one which can be used (and retains its basic character)
in a<ueous solution?
a) O%H3

b) $

c& OH

d) %"H3O"

e) H?O

1. + product of the reaction! %H3%H"*i & ,"O is

a) %H3%H"O,
b) %H3%H"%H"%H3
c) %H"2%H"
d& CH3CH22
e) %H3%H"O%H"%H3
1-. ;he (olecule or ion that is for(ed when an acid loses its proton is called the @@@@@@@@@@@@.
+nswer= conjugate base
10. + substance that can donate a lone pair of electrons is a @@@@@@ according to @@@@@@@ theor6.
+nswer= baseA *ewis
15. Write an e<uation to show the reaction between ethanol! %"H-OH and (eth6llithiu(! %H3*i.
,raw all non-bonding electrons and show electron flow with cur>ed arrows.
+nswer=
O
H
%H
3
*i
&
O *i
&
%H

&
1 1
1 1
3
&
1 1
1 1
3

14. Which of the following will be stronger base (less stabiliBed)? Wh6?

NH NH
2
NH
2
Con4gate bases3
N
-
NH
-
NH
-
1 2 3
#ll componds ha0e the charge on the same electronegati0e atom1
Compond 1 has the charge on an sp
2
hybridi5ed nitrogen( this , is more
electronegati0e it 6ill stabili5e the charge better1 Most acidic compond( then 6ea7er
base1
Componds 2 and 3 ha0e the charge on sp
3
hybridi5ed nitrogen1
Compond 2 has an al7yl grop on the alpha carbon that donates electron density it
destabilizes the charge ma7es the compond less acidic8
compond 3 does not ha0e this e--ect then con4gate base 3 is more stable1
9he least stabili5ed "more destabilized& base 6ill be the stronger base( so the order goes
-rom more basic to less basic "that is3 less acidic to more acidic&3

NH
NH
2
NH
2
>
>
-