I ,.

CH3
I
CH - CI - CHa - CH. J
3

COOH
(a) 2,2~Dimethylbutanoic acid
(b) 2-Carboxyl--2-methylbutane
(c) 2-Ethyl-2-methylpropanoic acid
(d) 3-Methylbutanecarboxylic acid (2020)
9s.. Write the IUPAC name of the compound :
CH3- C H -C H2-C O O H
I
OH (Delhi 2014)
99. Write the IUPAC name of the following :
0
II H
C H :rC =C -C H =C H -C -O
(Delhi 2011C)
100. Write the IUPAC name of
COOH

I
Br Cl (AI 2011C)
l
,. -
~ ~rrite strud ures of compounds A a d .
tOt. · ll · n B 1n
ead' (_'1' the to owing reaction.
CH2CH3

KM110 4 - KOH +
830
-----~>A ----~ ➔ B
(1/2, Delhi 2019)

102. How do you convert the following :

Toluene to benzoic acid? (112, 2018)

103. Do the following conversion in not more

than two steps :
Ethyl benzene to benzoic acid
(1/3, Delhi 2017)
104. Name the reagent used in the ·following
reaction:
C6H5-CH2 -CH 3 ? > c 6H
~ s-coo-K+
(112, Delhi 2015)
 efer to answer 65 ( ii) .
(ii) R
9 7. (a) 1
f 4 3 2
- ? H - C H - C O O H
•
►
9 8. CH3 2

OH
cid
3-Hyd ro x yb u ta n-1-oic a

9 ~ H ex -2- e n - 4 - y n - o ic acid
9
- 5 - c h lo r o b e n z o ic acid
100. 3-Bromo

K M n 04 - KOH
101. I >

COOK COOH

Ho+
3 >
(B)
(A )
Ben zoi( J(iJ
Pota~s iun1 be n zoate
f'fl.l" . ,,

COOlI

102,
Tolue11e Be11zoic acid

~ l,.,.- CH2CH3(i) KMnO.fOH~ ,::;;" I COOH

103, ~
('")
ll
H 0+
3
.
~

Ethylbenzene Benzoic acid

104. Alkaline potassium permanganate (KMnO4,

KOH)
0
H2S04 II
105. CH= CH + H 20 so >CH 3-C-H
Acetylene g 4 I~[O]
I

CH 3COOH
Acetic acid

\ KMn0 4 -H2S0 4 ),
COOH
106.
Heat cooH
Hexane-1,6-dioic acid
Cyclohexene l Ad inic a(id)
I I I . " ·- it4;' th e :- t ru
,.: t n r e s o t A , B, L ,
l ) an d f:, in th e
frl~t..-rwi n g rea c ti o n s
:
C fi-:::C O C l
- - >A -----------=-~
Z n - H g /c o n c .HC l
.A-n h yd . AIC1 3 i· N a O I
>B
(i ) K M n O 4
KOH, fl.
-ri) H 3o+
D+E
C
(Delhi 2 016)
 • • A

(i ii )

Be nz oi c ac id ' Br
~ B
11 I. .. . . ron1ob enzoic ac id

0
11
C H3c oc 1
1 "- C H 3 Zn-Hg
Anhyd. A IC it Conc.HCl
(A )
COOH
I < (i) K M n04 - KOH, Ii
(ii) H 3o+
(C) (B)
COONa
A Nao~ +CHI 3
(D)
(E)
In cr ea si n g o rd er o f bo il in g po in t:
112.
H O < C H 0 H < C H -C O OH
CH -C 3 2 5 3 ~ "!"''"'1:

n f electro11 withdra .
12.8 Physical Properties
VSA (1 mark)
112. Arrange the tallowing in the increasing orde1
of their boiling points.
CH3CHO, CH3COOH, CH3CH20H
(1/5, AI 2016, 2015)

12.9 Chemical Reactions

DB_o_mark) - - - -
113. Assertion (A) : Benzoic acid does not
undergo Friedal-Crafts reaction.
Reason (R) : The carboxyl group is activating
and undergo electrophilic substitution
reaction.
(a) Both Assertion (A) and Reason (R)
are correct statements, and Reason
(R) is the correct explanation of the
Assertion (A).
(b) Both Assertion (A) and Reason (R) are
correct statements, but Reason (R) is not
the correct explanation of the Assertion
(A).
(c) Assertion (A) is correct, but Reason (R)
is incorrect statement.
(d) Assertion (A) is incorrect, but Reason
(R) is correct statement. (2 020)
T
 ~ lZ) ,s correc\ s,a,cn1 cnt. \ ~ V ~ l/ }

114. Compkte- the fo llowin

g reaction :
l~l-l ~
\ · (i) Br2/Red P4
CH ,- CH - COOH (ii)H 20
➔
(1/3, Delhi 2019)
HS . Write the structure of
major product(s) in
the fallowing :
COOH

NaOH
> (1/5, A I 2019)

11 6 . Carry o ut the followin

g conversions:
Propanoic acid to acetic acid
. (1/5, A I 2019)
117 Do the following co
&

nversion in not more

than two steps :
Benzoic acid to benzaldehyde.
(1/3, Delhi 2017, 1/5 Delhi 20
15C)
118. Why carboxylic ac
id does not give reactions
of carbonyl group?
(1/5, A I 2017C, 1/5, A l 2
016)
 CH3
I (i) Br/ Red P4
114. CH --CH - COOH - -- ~
3 (ii) H20 CH
r 3
CH3 -- C- COOH
I
Br
2- Brorno- 2- methvl
propanoic ac1d
 115.
COOH - +
COONa

NaOH
➔
Q

116. CH 3CH 2COOH (i) NaOH > CH -CH

(ii) CaO/d 3 I 3
~ Br2, hu
KOH
CH3CH20H < <aql CH CH2Br
3
!KMn04
CH 3COOH
117.
COOH COCl

soc12 > 0 H2/Pd-S, BaSO4 >

Rosenmund's reduction
BenEoic acid Benzoyl chloride
CHO

I •
Benzaldehyde
 CH3 CH2 0H ~ KOH( aq)
i Bri, ht1

CH 3CH 2 Br
!KM no4
CH3 COO H
II 7.
COO H
COC l
soc12
>
Rose nmun d's redu ctio:
BenE oic acid
Benz oyl chlor ide
CHO

Benz aldeh yde

118. The carb onyl grou p in -CO OH is inert
and does not show nucl eoph ilic addi tion react ion
like carb onyl com poun d. It is due to reson ance
stab ilisa tion of carb oxyl ate ion :
R-C ==O < > R- c-o -
1 11
o- 0
_ • _J _ -- .l _, 1
 , - •Q~s 1<
I 19. L~ i, rc sin1i~Ie cl1e111ical tests to di· t·
hdw cei1 the follo wing pairs of com ps •ngu·18h
Benzoic acid and ethy l benz oate ou nds :
r (1/5, AI 2017 C, 1/3, Fore ign
2014;
120. Dist ingu ish betw een
CH3 COO H and HCO OH (112, AI )
2016
121. Pred ict the prod ucts of the follo wing reaction .
.
NaO H/Ca O
CH3 C00 Na . 11 > ? (113, Delhi 2015)
122. Nam e the reag ent used in the following
reac tion :
?
CH3-CO OH . > CH 3-CO C1
(1/2, Foreign 2015)
123. Write the main prod uct in the . following
equa tion :
PC1 5
CH 3-CO OH --- .> (1/5, Delh i 2015C)
124. Describe the follo wing givin g chemical
equa tion :
Decarboxylation reac tion )
r 1/.t;_ Delh i 201 SC, 201 2
119. Ben zt")i(" a l'h:l a11(l etl1yl b e11zoate can be
d istinguis l1t~,1 1~, . tl1eir reaction s with sodium
~

b i(:arbt~11ate solt1tion . Be11zoic acid will give

e fter v·es("en("e "'ritl1 NaHC0 3 whereas ethyl
ben ::oate does n o t react.
1 2 0 . . ;. \dd Tollen s' reagent to formic acid and
'-'-a:-m . Silver mirror is formed.
HCOOH + 2 [Ag(NH 3)i]+ + 20H- Warm>
Formic a cid
2Ag + CO 2 + 2NH 3 + 2NH 40H
Silver mirror
Ace tic acid does not give this test.
121. CH 3 C OONa NaO~Ca O > CH4 + Na2 C0 3
Methane
PCl 5
122. CH 3 - COOH ➔ CH 3 -COC1 + POC13
+ HCI
 123. Refer to answer 122.
124. Decarboxylation : Sodium or potass
.
salt of carboxy1IC .d h . 1urn
ac1 s on eatin g with soda lime
(NaOH and CaO), loses a molecule of carb
dioxide an d alkanes are o bta1ned as products. on
n

0
II
R- C-0 -N a + + NaOH Ca o >R -H + Na7 CO,
- ~'

•
125. Refer to answer 118.
126. Phenol an d benzoic acid can be disti
nguished
by their reactions with sodium bicarbonate soluti
on.
Benzoic acid will give effervescence with NaHC
O) 1
bu t phenol will no t re ac t.
I
 \ l)
~ ou nt for th e fo llo wi ng :
131 • ,f\.c c . . •
la) Arom at ic ca rb ox yh c ac id s
do no t
un de rg o Fr ie de l-C ra fts reaction. (i

(b ') -pKavalue of 4- ni tro be nz oi c acid is lower 13 9. <

th an th at of be nz oi c acid. (2018)
132. W rit e th e re ac tio ns in vo lv ed in th e following:
(i) H el l- V ol ha rd -Z el in sk .y re ac tio
n
(ii) D ec ar bo xy la tio n re ac tio n (Delh
i 2017)
133. (a) W ri te th e pr od uc t in th e fo
llo w in g
reactio n : 14
'? ' COONa cao
\ +N aO H -~➔ 1•
~ !:::,,.

(b ) Give simple chemical test to distingui

sh
be tw ee n th e following pair of co m po un ds :
Be nz oi c ac id an d ph en ol (2/5, AI 2017)
I3 l. , a) Due to presence of electron withdra·,::t?
group (-COOH) in aromatic carboxyik ir:ct
thcv do not undergo Friede]-Crafts reactiu::.
'
t, i Due to presence of strong el::~:- -
withdrawing group (-N 02), 4-ni trobenzoi~a::1d
is more acidic than benzoic acid and tb.e!"e:: ~;
pKavalue is lower.
All)V' I

i) Refer to answer 127.

(
132·
. Refer to answer 124.
111) J'
\

~ COONa
13 (a) \ + NaOH _Cao
lJ. ~ fl ➔

sodium be111.<,ate

Ben,zene

(b) Refer
•
to cuisw~r 126.
134. ti) Acetophenone to benzoic acid :
 w ill yo u co nv er t th e follow ing in not
134. H ow
n1ore th an tw o st ep s :
(i) A ce to ph en on e to benzoic acid l
an oi c ac id to 2-hy drox yeth anoic
(ii) Eth
acid (2/5, A I 2017)
wing reaction:
I
135. (a) Write the product of the follo
1
C H C O O H Clz/P >
3

Giv e si m pl e ch em ic al te st to distinguish
(b)
be tw ee n th e foil owing pair
of

co m p o u n d s:
Benzaldehyde and benzoic acid
(2/5, Delhi 201.J)
(lJ) Ref er to answer 126.
134, (i) Acetophenone to b .
0 enzo1c acid :
0

NaOCI ONa + CH'.13

➔

1~cetophenone

0
OH

Benzoic acid
(ii) Ethanoic acid to 2-hydroxyethanoic acid.
CH COOH Clz/Red P > Cl-CH2-COOH
3
Ethanoic acid HzO · 2-Chloroethanoic acid

NaOH ➔ HO- CH2-COOH

2-Hydroxyethanoic acid
f""'L IP
 2-- f 1yd
roxyethanoic acid
Cl 2/P
135. (a) CH3COOH ➔ ?H2COOH
Cl
(b) Benzaldehyde when treated with
ammoniacal silver nitrate gives silver mirror.
C6H5CHO + 2[Ag(NH3)i]+ + 30H- ➔
C6H5COO- + 2Ag + 4NH3 + 2H20
Silver mirror
Benzoic acid does not give this test.
Benzoic acid reacts with sodium bicarbonate to
liberate CO 2.
COOH COONa

Benzoic acid
I •

1 4 2. \ \Tri te th e st ru ct u res
o f co m p o u n d s A, B an d
C in ea ch o f th e fo ll o w in g
) re ac ti o n s :
M g/ dr y et he r (a) C 0 2 (g)
(i) C6 H 5Br >A ➔ B
(b) H 30 + tP C ls

(i i) CH CN (a) SnC12/H C l > A d il . N aO H > B

3 (b) H30+
t~
C
(Delhi 2017)
 t·: st{)r
142. (i)
l~ r
fl ·~ Mg/d r y ether MjJRr
(✓' - ➔ ( a) r~,)
Ug)
() (A ) (bH\ o • )
Ii 0
~ c - OH 11
u J
PC~·-➔ "
C --c1

B
(C)
·: r H - C = - N (a) SnC
(lJ ; __, 13 - (b) H6+l~/HCl C .
'" , =)
~
H3-C-H
3 (A)
idil. NaOH
0
CH 3 CH=<: H -C11 -H ◄ 6 ?H¥ ~
( (; )
CH3 -~-9-c-H
Ii H
(8)