Carboxylic Acids

1) The combination of a carbonyl group and a hydroxyl group on the same carbon atom is called
a __________ group.
A) carbamate
B) carbonate
C) urethane
D) carboxyl
E) carboxylate
Anser! D
Diff! 1

") The common name for pentanedioic acid is!
A) pimelic acid
B) oxalic acid
C) glutaric acid
D) succinic acid
E) adipic acid
Anser! C
Diff! "

#) $ro%ide the structure of #&#'dimethylheptanoic acid.
Anser! C(
#
C(
"
C(
"
C(
"
C)C(
#
)
"
C(
"
C*
"
(
Diff! 1

+) $ro%ide the structure of glutaric acid.
Anser!
Diff! "

,) $ro%ide the name of the compound shon belo.
Anser! "&,'dimethyl'+'hexenoic acid or "&,'dimethylhex'+'enoic acid
Diff! "

1
-) $ro%ide the ./$AC name for (*
"
CC(
"
C)C(
#
)
"
C(
"
C(
"
C*
"
(.
Anser! &#'dimethylhexanedioic acid
Diff! 1

0) $ro%ide the ./$AC name for the compound shon belo.
Anser! o'hydroxyben1oic acid or "'hydroxyben1oic acid
Diff! 1

2) $ro%ide the ./$AC name for the compound shon belo.
Anser! E'"&,'dimethyloct','enoic acid
Diff! 1

3) $ro%ide the ./$AC name for the compound shon belo.
Anser! 'hydroxyhexanoic acid
Diff! 1

14) $ro%ide the structure of trans'1&#'cyclohexanedicarboxylic acid.
Anser!
Diff! 1

11) $ro%ide the structure of pent'#'ynoic acid.
Anser! C(
#
C5CC(
"
C*
"
(
Diff! 1

"
1") $ro%ide the structure of #'nitrophthalic acid.
Anser!
Diff! 1

1#) $ro%ide the structure of succinic acid.
Anser! (*
"
C C(
"
C(
"
C*
"
(
Diff! "

1+) Carboxylic acids boil at considerably higher temperatures than do alcohols& 6etones& or
aldehydes of similar molecular eights. This is because they!
A) ha%e a greater oxygen content.
B) are more acidic.
C) form stable hydrogen'bonded dimers.
D) are hydrophobic.
E) none of the abo%e.
Anser! C
Diff! 1

1,) Are carboxylic acids of more than 14 carbons more soluble in polar or nonpolar sol%ents7
Anser! nonpolar sol%ents
Diff! 1

1-) Dra an acetic acid dimer. Be sure to indicate the hydrogen bonds present.
Anser!
Diff! "

#
10) 8hy are the *( groups of carboxylic Acids more acidic than alcohols7
A) resonance stabili1ation of the carboxylate ion
B) inducti%e electron donating by the carbonyl oxygen
C) reduced hydrogen bonding capacity
D) because they ha%e loer p9a %alues
E) none of the abo%e ' carboxylic acids are not more acidic than alcohols
Anser! A
Diff! 1

12) :ist the folloing ea6 acids in order of increasing acidity )from loest to highest.).
A) + ; # ; " ; 1 ; ,
B) + ; 1 ; # ; " ; ,
C) , ; " ; # ; 1 ; +
D) + ; 1 ; " ; , ; #
E) 1 ; " ; + ; # ; ,
Anser! B
Diff! 1

13) 8hich of the folloing is the strongest acid7
A) acetic acid
B) chloroacetic acid
C) bromoacetic acid
D) fluoroacetic acid
Anser! D
Diff! "

"4) 8hich of the folloing is the strongest acid7
A) chloroacetic acid
B) dichloroacetic acid
C) trichloroacetic acid
D) acetic acid
Anser! C
Diff! "

+
"1) The strongest dichlorobutanoic acid is!
A) "&"'dichlorobutanoic acid
B) "&#'dichlorobutanoic acid
C) #&#'dichlorobutanoic acid
D) #&+'dichlorobutanoic acid
E) +&+'dichlorobutanoic acid
Anser! A
Diff! "

"") 8hich of the folloing compounds is the strongest acid7
A) p'nitroben1oic acid
B) p'bromoben1oic acid
C) m'methylben1oic acid
D) m'methoxyben1oic acid
E) ater
Anser! A
Diff! "

"#) 8hich of the folloing is the strongest acid7
A) )C(
#)"
C(C*
"
(
B) C(
#
C(
"
C*
"
(
C) C(
#
*C(
"
C*
"
(
D) $hC(
"
C*
"
(
E) *
"
<C(
"
C*
"
(
Anser! E
Diff! "

"+) 8hich of the folloing statements is true7
A) At to p( units abo%e the p9a& the carboxylate ion concentration exceeds the concentration
of the carboxylic acid by a 144 to 1 ratio.
B) At to p( units abo%e the p9a& the carboxylate ion concentration exceeds the concentration
of the carboxylic acid by a " to 1 ratio.
C) At to p( units belo the p9a& the carboxylate ion concentration exceeds the concentration
of the carboxylic acid by a " to 1 ratio.
D) At to p( units belo the p9a& the carboxylate ion concentration exceeds the concentration
of the carboxylic acid by a 14 to 1 ratio.
E) At to p( units belo the p9a the carboxylate ion concentration is e=ual to the carboxylic
acid concentration.
Anser! A
Diff! "

,
",) At p( +.,& hich of the folloing acids ould be most dissociated7
A) p'nitroben1oic acid )p9
a
> #.+1)
B) acetic acid )ethanoic acid) )p9
a
> +.0+)
C) hexanoic acid )p9
a
> +.22)
D) octanoic acid )p9
a
> +.23)
E) ater
Anser! A
Diff! #

"-) 8hat salt results from the reaction of ben1oic acid ith potassium hydroxide7
Anser! potassium ben1oate
Diff! 1

"0) <ame the salt formed from the reaction of acetic acid ith ammonia.
Anser! ammonium acetate
Diff! 1

"2) An un6non compound is insoluble in ater but dissol%es in sodium bicarbonate ith a
release of carbon dioxide bubbles. The compound is almost certainly!
A) a carboxylic acid
B) an amine
C) an aldehyde
D) an al6yl chloride
E) an alcohol
Anser! A
Diff! 1

"3) An ether solution of $hC*
"
( )A)& $h<(
"
)B)& and $hC(
#
)C) is extracted ith a=ueous
<a*(. The ether layer ill contain hat compound)s) after the extraction7
A) A ? B
B) A ? C
C) B ? C
D) A ? B ? C
E) A only
Anser! C
Diff! 1

-
#4) After completing the synthesis of #'methylpentanoic acid& hich of the folloing treatments
ill neutrali1e the mineral acids and facilitate the distribution of the organic acid from the
organic layer to the a=ueous extraction layer7
A) Extraction ith a=ueous <aCl.
B) Extraction ith ether.
C) Extraction ith a=ueous <a(C*
#.

D) Extraction ith ater.
E) Extraction ith dilute a=ueous (Cl.
Anser! C
Diff! 1

#1) .n the propanoate ion&!
A) both the carbon'oxygen bonds are the same length.
B) the carbon'oxygen double bond is shorter.
C) the carbon'oxygen double bond is longer.
D) one of the oxygen atoms bears a '1 charge.
E) the carbon atom bears a '1 charge.
Anser! A
Diff! "

#") 8hat products result from the reaction of sodium propanoate ith hydrobromic acid7
Anser! propanoic acid and sodium bromide
Diff! 1

##) $ro%ide the structure of 1inc undecanoate& a ma@or component in se%eral athleteAs foot
medications.
Anser! BnC*
"
C)C(
"
)
3
C(
#
D
"
Diff! "

#+) $ro%ide the ma@or organic product of the reaction shon belo.
Anser!
Diff! "

0
#,) /sing acid'base extractions& ho might you purify a crude sample of ben1oic acid7
Anser!
1. Dissol%e sample in ether.
". Extract ith ater to remo%e ater'soluble impurities.
#. Extract ith sodium bicarbonate to separate ben1oate from organic impurities.
+. Acidify a=ueous layer and extract ben1oic acid into ether.
,. Dry ether layer& filter to remo%e drying agent& and e%aporate ether to gi%e purified ben1oic
acid.
Diff! "

#-) 8here ould one expect to find the
1
( <EF signal for the carboxyl groupAs hydrogen in
propanoic acid7
A) G +.1 ' ,.- ppm
B) G 14 ' 1# ppm
C) G 2 ' 3 ppm
D) G -.1 ' 0.2 ppm
E) G 3., ' 14 ppm
Anser! B
Diff! 1

#0) 8hich of the folloing statements is true7
A) The carbonyl carbon in a carboxylic acid does not gi%e a
1#
C signal in a
1#
C'<EF spectrum.
B) The carbonyl carbon in a carboxylic acid gi%es a
1#
C signal in the same region as a carbonyl
carbon from a 6etone or aldehyde ' in the range of "44 ppm.
C) The carbonyl carbon of a carboxylic acid splits a proton signal into a doublet in an ('<EF
spectrum.
D) The carbonyl carbon in a carboxylic acid gi%es a
1#
C signal in the same region as a carbonyl
carbon from an ester or amide in the range of 1,4 to 124 ppm.
E) The carbonyl carbon in a carboxylic acid cannot be distinguished from an aromatic carbon
because they both gi%e signals in the range of 114 to 1#4 ppm.
Anser! D
Diff! 1

2
#3) 8hat to features are prominent in the infrared spectrum of a carboxylic acid7
Anser! The carbonyl stretch at H1014 cm
'1
and the hydroxyl stretch beteen ",44 and
#,44 cm
'1
.
Diff! 1

+4) (o does the *'( stretch in the .F spectrum of a carboxylic acid differ from the *'( stretch
of an alcohol7
Anser! The *'( stretch of a carboxylic acid is broader and shifted to loer a%enumbers.
Diff! "

+1) Deduce a reasonable structure for the compound hich exhibits the folloing spectroscopic
data.
C
,
(
3
Cl*
"
! .F! "044'#+44 cm
'1
)broad)& 1014 cm
'1
I
1
( <EF! _ 1.+4 )-(& singlet)& #.-4 )"(&
singlet)& 14.1 )1(& singlet) ppm.
Anser! )C(
#
)
"
CClC(
"
C*
"
(
Diff! #

+") Carboxylic acids can be made from Jrignards by treating the Jrignard reagents ith!
A) carbon monoxide
B) esters
C) aldehydes
D) diborane
E) carbon dioxide
Anser! E
Diff! 1

+#) An acid hich could not be prepared by the reaction of an organic halide ith cyanide ion
folloed by acid hydrolysis of the nitrile is!
A) propanoic acid
B) phenylacetic acid
C) acetic acid
D) )C(
#)#
CC*
"
(
E) C(
#
)C(
"
)
1+
C*
"
(
Anser! D
Diff! "

3
++) An acid hich could not be prepared from an organic halide by carboxylation of the
Jrignard reagent is!
A) ben1oic acid
B) "&"'dimethylpropanoic acid
C) propanoic acid
D) +'oxocyclohexanecarboxylic acid
E) "'methylbutanoic acid
Anser! D
Diff! "

+,) 8hat compound is produced hen cyclohexene is treated ith concentrated 9En*
+
7
A) hexanoic acid
B) adipic acid
C) cyclohexanecarboxylic acid
D) ben1oic acid
E) succinic acid
Anser! B
Diff! "

+-) 8hat compound is produced hen )C(
#
)
"
C(C(
"
Br is sub@ected to the folloing se=uence
of steps! 1. Eg& Et
"
*& ". C*
"
& #. (
#
*
?
7
A) "'methylpropanoic acid
B) #'methylpropanoic acid
C) "'methylbutanoic acid
D) #'methylbutanoic acid
E) "'methylhexanoic acid
Anser! D
Diff! "

14

+2) 8hich se=uence of steps belo describes the best synthesis of ,'oxohexanoic acid starting
ith 1'methylcyclopentan'1'ol
A) 1. Conc. 9En*
+
". Dry gaseous (Br
#. mgKether
+. C*
"
B) 1. (
"
L*
+
and heat
". Conc. 9En*
+
C) 1. Conc. 9En*
+
". C(
#
EgBrK ether
#.
(
#
*
?
D) 1. (
"
L*
+
and heat
". *
#
#. )C(
#
)
"
L
+. $CC
E) 1. (
"
L*
+
and heat
". Conc. 9En*
+
#. :iAl(
+
+. (
#
*
?
Anser! B
Diff! #

11
+3) 1'(exanol reacts ith chromic acid to yield hat product7
Anser! (exanoic acid
Diff! 1

,4) $ro%ide the ma@or organic product of the folloing reaction.
Anser!
Diff! "

,1) $ro%ide the ma@or organic product of the folloing reaction.
Anser!
Diff! "

,") $ro%ide the ma@or organic product of the folloing reaction.
Anser!
Diff! "

1"
,#) $ro%ide the ma@or organic product of the folloing reaction.
Anser!
Diff! "

,+) $ro%ide the ma@or organic product of the folloing reaction se=uence.
Anser!
Diff! "

,,) $ro%ide the ma@or organic product of the folloing reaction se=uence.
Anser!
Diff! "

1#
,-) $ro%ide the ma@or organic product of the folloing reaction se=uence.
Anser!
Diff! "

,0) $ro%ide the se=uence of reagents needed to accomplish the con%ersion belo.
Anser!
1. B(
#
MT(N
". (
"
*
"
& (*
'
#. <a
"
Cr
"
*
0
Diff! "

,2) $ro%ide the ma@or organic product of the folloing reaction se=uence.
Anser!
Diff! "

1+
,3) $ro%ide the ma@or organic product of the reaction shon belo.
Anser!
Diff! "

-4) $ro%ide the ma@or organic product of the reaction shon belo.
Anser!
Diff! "

-1) $ro%ide the ma@or organic product of the reaction shon belo.
Anser!
Diff! "

1,
-") Luggest a se=uence of synthetic steps through hich p'toluic acid can be prepared from
toluene.
Anser!
1. Br
"
& NeBr
#
". Eg& ether
#. C*
"
+. (
#
*
?
Diff! #

-#) $ro%ide the ma@or organic product of the folloing reaction.
Anser!
Diff! #

-+) $ro%ide the ma@or organic product of the folloing reaction.
(C)*C(
"
C(
#
)
#

Anser! (C*
"
( ? C(
#
C(
"
*(
Diff! #

-,) "'$henylethanol yields hat acid upon treatment ith cold chromic acid7
Anser! phenylacetic acid
Diff! 1

--) 8hat to al6enes& hich contain only one double bond& yield exclusi%ely propanoic acid
upon oxidation ith hot concentrated 9En*
+
7
Anser! E' and Z-hex'#'ene
Diff! "

1-
-0) "'$henylethanol yields hat acid upon treatment ith hot chromic acid or permanganate7
Anser! ben1oic acid
Diff! "


-3) $ropose a reasonable synthetic route to prepare cyclohexylacetic acid from
methylenecyclohexane.
Anser!
1. (Br& peroxides
". Eg& ether
#. C*
"
+. (
?
& (
"
*
or
1. (Br& peroxides
". <aC<& acetone
#. (
?
& (
"
*
Diff! "

04) Luggest a se=uence of synthetic steps through hich phenylacetic acid can be prepared from
toluene %ia phenylacetonitrile.
Anser!
1. Br
"
& hO or <BL
". <aC<& acetone
#. (
?
& (
"
*
Diff! #

01) Luggest a se=uence of synthetic steps through hich phenylacetic acid can be prepared from
toluene and in hich Jrignard chemistry is employed.
Anser!
1. Br
"
& hO or <BL
". Eg& ether
#. C*
"
+. (
?
& (
"
*
Diff! #

10
0#) 8hich of the folloing conditions ill dri%e the e=uilibrium of the Nischer esterification
toards ester formation7
A) addition of ater
B) remo%al of ater as it is formed
C) addition of an inorganic acid as a catalyst
D) addition of alcohol
E) both B and D
Anser! E
Diff! #
4
0+) $ro%ide the ma@or organic product of the reaction shon belo.
Anser!
Diff! "
4
0-) The methyl ester of a carboxylic acid can be synthesi1ed directly using!
A) L*Cl
"
B) $Cl
,
C) C
"
*
"
Cl
"
D) C(
"
<
"
E) C(
#
<(
"
Anser! D
Diff! 1
1
00) 8hich of the folloing reactions in%ol%es the formation of a methyl ester from a carboxylic
acid7
A) Cope elimination
B) (ell'Polhard'Belins6y reaction
C) reaction ith C(
"
<
"
D)
(unsdiec6er reaction
E)
hydroboration ith diborane
Anser! C
Diff! 1
1
12
02) $ro%ide a detailed& stepise mechanism for the methylation of a carboxylic acid ith
dia1omethane.
Anser!
Diff! #
1
2#) :ithium aluminum hydride reduces carboxylic acids to primary alcohols %ia hat
intermediate7
A) a 6etone
B) a methyl ester
C) an aldehyde
D) a secondary alcohol
E) an acid chloride
Anser! C
Diff! #


20) $ro%ide the ma@or organic product of the reaction shon belo.
Anser!
Diff! "


23) $ropose a reasonable synthetic route to prepare butanal from butanoic acid.
Anser!
1. :iAl(
+
". $CC
or
1. L*Cl
"
". :iAl(C*C)C(
#
)
#
D
#
Diff! 1

13
34) $ro%ide the ma@or organic product for the folloing reaction.
Anser!
Diff! "

31) $ro%ide the ma@or organic product for the folloing reaction.
Anser!
Diff! "

3#) Luggest a se=uence of synthetic steps through hich "'phenylethanol can be prepared from
toluene. *ne of your intermediates must be a carboxylic acid.
Anser!
1. Br
"
& hO or <BL
". <aC<& acetone
#. (
?
& (
"
*
+. :iAl(
+
or
1. Br
"
& hO or <BL
". Eg& ether
#. C*
"
+. (
?
& (
"
*
,. :iAl(
+
Diff! #


32) Beta'6eto acids are unusually unstable and ill lose the carboxylate group under certain
conditions here both a general acid and base are in%ol%ed. During this process& C*
"
is lost and
"4
the orginal beta'6eto acid is con%erted into a 6etone. Nor the folloing reaction& sho a stepise
mechanism& ith electron pushing arros & in the formation of the products. Ea6e special note
of any resonance stabili1ed intermediates in this reaction.

Anser!
Diff! #

"1

141) Acid chlorides can be prepared from carboxylic acids by treatment ith!
A) )C*Cl)
"
B) L*Cl
"
C) 9Cl
D) both A and B
E) both B and C
Anser! D
Diff! "

14") 8hich of the folloing reagents can be used to con%ert a carboxylic acid directly into its
corresponding acid chloride deri%ati%e7
A) )C*Cl)
"
B) (Cl
C) C(
#
Cl
D) <a*Cl
E) C(
#
C*Cl
Anser! A
Diff! "

14#) $ro%ide the ma@or organic product of the folloing reaction.
Anser!
Diff! 1

140) $ro%ide the ma@or organic product of the reaction shon belo.
Anser!
""
Diff! "

142) 8hat are the products of the reaction of ben1oic acid ith thionyl chloride7
Anser! ben1oyl chloride& L*
"
)g)& and (Cl)g)
Diff! "

143) 8hat are the products of the reaction of phenylacetic acid ith oxalyl chloride7
Anser! phenylacetyl chloride& (Cl )g)& C* )g)& and C*
"
)g)
Diff! "

"#