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Nomenclature of organic compounds Questions in English

Class 11 Chemistry · 8-1.Organic Chemistry : Classification and Nomenclature of Organic compounds · Nomenclature of organic compounds

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201
MediumMCQ
In the $IUPAC$ nomenclature system,what is the correct decreasing order of priority for the following functional groups?
A
$COOH > SO_3H > CONH_2 > CHO$
B
$SO_3H > COOH > CONH_2 > CHO$
C
$CHO > COOH > SO_3H > CONH_2$
D
$CONH_2 > CHO > SO_3H > COOH$

Solution

(A) According to the $IUPAC$ priority rules for functional groups,the order of priority is:
$COOH > SO_3H > CONH_2 > CHO > CN > ...$
Therefore,the correct decreasing order is $COOH > SO_3H > CONH_2 > CHO$.
202
MediumMCQ
Which statement is correct for the given compound?
Question diagram
A
Root word is $but-$.
B
Secondary suffix is $cyclo-$.
C
Primary suffix is $-ol$.
D
Primary prefix is $cyclo-$.

Solution

(D) The $IUPAC$ name of the given compound is $2-(3-methylbutyl)cyclopentan-1-ol$.
$1$. The parent chain is a $5$-membered ring,so the root word is $pent-$.
$2$. The ring is cyclic,so the primary prefix is $cyclo-$.
$3$. The functional group is $-OH$,so the secondary suffix is $-ol$.
$4$. The primary suffix is $-an-$ (for saturated ring).
Therefore,the statement 'Primary prefix is $cyclo-$' is correct.
203
EasyMCQ
Give the $IUPAC$ name of the compound: $CH_3CH=CHCOOC_2H_5$
A
Ethyl but-$2$-enoate
B
Ethyl but-$2$-oate
C
Ethyl prop-$2$-enoate
D
None of these

Solution

(A) The given compound is an ester: $CH_3CH=CHCOOC_2H_5$.
$1$. Identify the alkyl group attached to the oxygen atom of the ester functional group,which is an ethyl group $(-C_2H_5)$.
$2$. Identify the parent carboxylic acid chain containing the double bond. The chain has $4$ carbon atoms,so the root is 'but'.
$3$. The double bond is at the $2^{nd}$ position,so it is 'but-$2$-ene'.
$4$. The suffix for an ester is '-oate'.
$5$. Combining these,the name is 'Ethyl but-$2$-enoate'.
204
EasyMCQ
Provide the $IUPAC$ name for the given compound.
Question diagram
A
$3-$methylhexane
B
$3-$ethylhexane
C
$2-$ethylpentane
D
$3-$methylheptane

Solution

(A) $1$. Identify the longest carbon chain. The longest chain in the given structure has $6$ carbon atoms,so the parent alkane is hexane.
$2$. Number the chain from the end that gives the substituent the lowest possible number. Numbering from left to right,the substituent (methyl group) is at position $3$.
$3$. The substituent is a methyl group $(-CH_3)$ attached to the $3^{rd}$ carbon.
$4$. Therefore,the $IUPAC$ name is $3-$methylhexane.
205
AdvancedMCQ
What is the $IUPAC$ name of the given compound?
Question diagram
A
Bicyclo $[1, 2, 1]-$octane$-2, 6-$dione
B
Bicyclo $[1, 2, 2]-$octane$-2, 6-$dione
C
Bicyclo $[2, 2, 2]-$octane$-2, 6-$dione
D
Bicyclo $[1, 1, 1]-$octane$-2, 6-$dione

Solution

(C) The given structure is a bicyclic compound.
To name it,we identify the bridgehead carbons.
There are two bridgehead carbons connected by three bridges.
Counting the number of carbon atoms in each bridge:
- The bridge between the bridgehead carbons contains $2$ carbons.
- The other two bridges also contain $2$ carbons each.
Thus,the bicyclo system is $[2, 2, 2]$.
The total number of carbon atoms is $8$,so the parent alkane is octane.
The ketone groups are at positions $2$ and $6$.
Therefore,the $IUPAC$ name is Bicyclo $[2, 2, 2]-$octane$-2, 6-$dione.
206
MediumMCQ
Give the $IUPAC$ name of the following compound.
Question diagram
A
$3,4-$Dihydroxybenzoic acid
B
$2,3-$Dihydroxybenzoic acid
C
$4-$Carboxy$-2-$hydroxy phenol
D
$4-$Carboxybenzene$-1,2-$diol

Solution

(A) $1$. Identify the principal functional group: The $-COOH$ group has higher priority than the $-OH$ group,so the parent chain is a benzoic acid derivative.
$2$. Number the ring: Assign the carbon attached to the $-COOH$ group as position $1$. The $-OH$ groups are then at positions $3$ and $4$.
$3$. Name the substituents: There are two hydroxy groups at positions $3$ and $4$,so it is $3,4-$dihydroxy.
$4$. Combine: The full name is $3,4-$dihydroxybenzoic acid.
207
EasyMCQ
Provide the $IUPAC$ name of the compound: $CH_3-CH(OH)-CH_2-CH_2-CH_2-C(Br)_2-CH_3$
A
$6,6-$dibromoheptan$-2-$ol
B
$2,2-$dibromoheptan$-2-$ol
C
$6,6-$bromoheptan$-2-$ol
D
None of these

Solution

(A) $1$. Identify the longest carbon chain containing the principal functional group $(-OH)$. The chain has $7$ carbons,so the parent alkane is heptane.
$2$. Number the chain from the end that gives the lowest locant to the principal functional group $(-OH)$. Numbering from left to right,the $-OH$ group is at position $2$.
$3$. Identify substituents: Two bromine atoms are at position $6$. Thus,it is $6,6-$dibromo.
$4$. Combine: $6,6-$dibromoheptan$-2-$ol.
208
DifficultMCQ
Give the $IUPAC$ name of the compound shown in the image.
Question diagram
A
Bicyclo $[2.1.0]$ pentane
B
$1,2-$cyclopropylcyclobutane
C
Cyclopentane $(4.3)$ annulene
D
$1,2-$methylenecyclobutane

Solution

(A) The given structure is a bicyclic compound consisting of a cyclobutane ring fused with a cyclopropane ring sharing a common bond.
According to $IUPAC$ nomenclature for bicyclic compounds,the bridgehead carbons are numbered first,followed by the longest bridge,then the shorter bridge,and finally the shortest bridge (the shared bond).
Here,the two bridgehead carbons are connected by a path of $2$ carbons,a path of $1$ carbon,and a path of $0$ carbons.
Thus,the name is bicyclo $[2.1.0]$ pentane.
209
DifficultMCQ
Identify the correct $IUPAC$ name for the given compound:
$CH_3-CH_2-C(CH_3)(N(CH_3)_2)-CH_2-CH_3$
A
$N,N-$dimethyl-$1-$methyl-$1-$ethylpropane
B
$3-$methyl-$3-(N,N-$dimethylamino$)$pentane
C
$N,N-$dimethylamino-$3-$methylpentane
D
$N,N,3-$trimethylpentan-$3-$amine

Solution

(D) $1$. Identify the longest carbon chain containing the functional group. The longest chain is a pentane chain ($5$ carbons).
$2$. The amino group $(-N(CH_3)_2)$ is attached to the $3^{rd}$ carbon.
$3$. The substituent on the nitrogen atom is two methyl groups ($N,N-$dimethyl).
$4$. There is also a methyl group at the $3^{rd}$ carbon position.
$5$. Combining these,the parent chain is pentan-$3-$amine. The substituents are two methyl groups on the nitrogen and one methyl group on the $3^{rd}$ carbon.
$6$. The correct $IUPAC$ name is $N,N,3-$trimethylpentan-$3-$amine.
210
MediumMCQ
Give the $IUPAC$ name of the following compound.
Question diagram
A
$2-$hydroxycyclopentene
B
cyclopent$-2-$en$-1-$ol
C
hydroxycyclopentene
D
cyclopent$-1-$ol

Solution

(B) $1$. Identify the principal functional group: The $-OH$ group is the principal functional group,so the suffix is $-ol$.
$2$. Number the ring: Start numbering from the carbon atom attached to the $-OH$ group as $C-1$. Then,number in the direction that gives the double bond the lowest possible locant.
$3$. Following this rule,the double bond starts at $C-2$.
$4$. The parent chain is a cyclopentene ring.
$5$. Combining these,the name is cyclopent$-2-$en$-1-$ol.
211
MediumMCQ
What is the correct $IUPAC$ name of the given compound?
$HOOC-CH_2-C(OH)(COOH)-CH_2-COOH$
A
$3-$carboxy$-3-$hydroxybutanedioic acid
B
$2-$hydroxypropane$-1,2,3-$tricarboxylic acid
C
$3-$hydroxybutanedioic acid
D
$2-$bis(carboxymethyl)$-2-$hydroxyethanoic acid

Solution

(B) The given structure is $HOOC-CH_2-C(OH)(COOH)-CH_2-COOH$.
To name this compound,we identify the longest carbon chain containing the maximum number of carboxylic acid groups.
The main chain is a propane chain with three carboxylic acid groups attached at positions $1, 2,$ and $3$.
There is a hydroxyl group $(-OH)$ attached at the $2^{nd}$ carbon.
Thus,the parent chain is propane and the functional groups are $1, 2, 3-$tricarboxylic acid.
Combining these,the $IUPAC$ name is $2-$hydroxypropane$-1, 2, 3-$tricarboxylic acid.
212
MediumMCQ
Provide the $IUPAC$ name of the given compound.
Question diagram
A
$1-$methyl$-5-$ethylcyclohex$-1-$ene
B
$5-$ethyl$-1-$methylcyclohex$-1-$ene
C
$4-$ethyl$-6-$methylcyclohex$-1-$ene
D
$1-$ethyl$-5-$methylcyclohex$-3-$ene

Solution

(B) $1$. Identify the principal functional group: The compound is a cyclic alkene. The double bond gets priority in numbering.
$2$. Numbering the ring: Start numbering from the double bond such that the substituents get the lowest possible locants. If we start at the carbon with the double bond and move towards the ethyl group,we get $1-$ethyl$-5-$methylcyclohex$-1-$ene. However,alphabetical order is followed for naming substituents.
$3$. Alphabetical order: Ethyl $(E)$ comes before Methyl $(M)$.
$4$. Correct numbering: To give the lowest locants to substituents while prioritizing the double bond,we number the double bond carbons as $1$ and $2$. If we assign $1$ to the carbon with the ethyl group and $2$ to the adjacent double bond carbon,the methyl group is at position $5$. This gives $1-$ethyl$-5-$methylcyclohex$-1-$ene.
$5$. Comparing with options: The correct name is $1-$ethyl$-5-$methylcyclohex$-1-$ene. Since this specific option is not listed,we re-evaluate the structure. The structure shows the double bond between two carbons. If we number the double bond as $1$ and $2$,and the ethyl group is at $1$ and methyl at $5$,the name is $1-$ethyl$-5-$methylcyclohex$-1-$ene. Looking at the provided options,option $B$ is $5-$ethyl$-1-$methylcyclohex$-1-$ene,which is the same structure if numbered differently. However,based on standard $IUPAC$ rules,$1-$ethyl$-5-$methylcyclohex$-1-$ene is preferred.
213
EasyMCQ
What is the $IUPAC$ name of $CH_3-CH_2-CH=C(CH_3)CH_2OH$?
A
$2-$methylpentyl alcohol
B
$4-$methyl$-3-$penten$-1-$ol
C
$2-$methylpent$-2-$en$-1-$ol
D
$4-$methylpentyl alcohol

Solution

(C) $1$. Identify the longest carbon chain containing the functional group $(-OH)$ and the double bond $(C=C)$.
$2$. The chain has $6$ carbons,but the longest chain containing the double bond and the $-OH$ group is a $5$-carbon chain (pentene).
$3$. Numbering starts from the carbon attached to the $-OH$ group to give it the lowest possible locant: $C1$ is the carbon attached to $-OH$,$C2$ is the carbon with the methyl group,$C3$ is the double bond start,$C4$ is $CH$,and $C5$ is $CH_3$.
$4$. The structure is $CH_3-CH_2-CH=C(CH_3)CH_2OH$. The parent chain is pent$-2-$en$-1-$ol.
$5$. There is a methyl group at position $2$.
$6$. Therefore,the $IUPAC$ name is $2-$methylpent$-2-$en$-1-$ol.
214
EasyMCQ
What is the $IUPAC$ name of the compound $CH_3-CH(C_2H_5)-CH(C_2H_5)-CH_3$?
A
$3, 4-$Dimethylhexane
B
$2, 3-$Dimethylbutane
C
$2-$sec-butylbutane
D
$2, 3-$Diethylbutane

Solution

(A) $1$. Identify the longest carbon chain. The structure is $CH_3-CH(CH_2CH_3)-CH(CH_2CH_3)-CH_3$.
$2$. The longest chain contains $6$ carbon atoms,so the parent alkane is hexane.
$3$. Number the chain from either end to give the lowest locants to the substituents. Numbering from left to right gives substituents at positions $3$ and $4$.
$4$. The substituents are two methyl groups at positions $3$ and $4$.
$5$. Therefore,the $IUPAC$ name is $3, 4-$dimethylhexane.
215
MediumMCQ
What is the common name of $2, 3$-dihydroxybutanedioic acid?
A
Maleic acid
B
Tartaric acid
C
Citric acid
D
Lactic acid

Solution

(B) The $IUPAC$ name $2, 3$-dihydroxybutanedioic acid corresponds to the structure $HOOC-CH(OH)-CH(OH)-COOH$.
This compound is commonly known as Tartaric acid.
216
EasyMCQ
What is the $IUPAC$ name of neopentane?
A
$2-$methylpropane
B
$2,2-$dimethylbutane
C
$2-$methylbutane
D
$2,2-$dimethylpropane

Solution

(D) Neopentane has the chemical structure $CH_3-C(CH_3)_2-CH_3$.
To determine the $IUPAC$ name,we identify the longest carbon chain,which contains $3$ carbon atoms (propane).
There are two methyl groups attached to the second carbon atom.
Therefore,the $IUPAC$ name is $2,2-$dimethylpropane.
217
MediumMCQ
Write the $IUPAC$ name of the given compound.
Question diagram
A
$2,4,6-$Heptatriene
B
$2,4,5-$Triheptene
C
$2,4,6-$Triheptene
D
Hepta$-1,3,5-$diene

Solution

(A) The given structure is a hydrocarbon chain with $7$ carbon atoms $(hept-)$ and $3$ double bonds $(triene)$.
Numbering the chain from the left to give the lowest possible locants to the double bonds,we get the positions $2, 4,$ and $6$.
Thus,the $IUPAC$ name is $2,4,6-$heptatriene.
218
MediumMCQ
What is the $IUPAC$ name of the given compound?
Question diagram
A
$trans-2-chloro-3-iodo-2-pentene$
B
$cis-2-chloro-3-iodo-2-pentene$
C
$trans-3-iodo-4-chloro-3-pentene$
D
$cis-3-iodo-4-chloro-3-pentene$

Solution

(B) $1$. Identify the longest carbon chain containing the double bond. The chain has $5$ carbons,so it is a $pentene$ derivative.
$2$. Number the chain to give the double bond the lowest possible position. Numbering from left to right gives the double bond at position $2$.
$3$. Substituents are $chloro$ at position $2$ and $iodo$ at position $3$. Thus,the base name is $2-chloro-3-iodo-2-pentene$.
$4$. Determine the configuration ($cis$ or $trans$). On the left carbon $(C2)$,the higher priority group is $Cl$ $(Z=17)$ vs $CH_3$ $(Z=6)$. On the right carbon $(C3)$,the higher priority group is $I$ $(Z=53)$ vs $CH_2CH_3$ $(Z=6)$.
$5$. Since the higher priority groups ($Cl$ and $I$) are on the same side of the double bond,the configuration is $cis$ (or $Z$).
$6$. Therefore,the correct name is $cis-2-chloro-3-iodo-2-pentene$.
219
MediumMCQ
What is the $IUPAC$ name of the given compound?
Question diagram
A
$2-$hydroxycyclopentanal
B
$2-$formyl$-1-$hydroxycyclopentane
C
$2-$hydroxycyclopentanecarbaldehyde
D
cyclopentane$-2-$ol$-1-$al

Solution

(C) In the given compound,the $-CHO$ group is directly attached to the cyclopentane ring. According to $IUPAC$ nomenclature rules,when a functional group like $-CHO$,$-COOH$,etc.,is directly attached to a ring,the carbon atom of the functional group is not included in the ring numbering. Instead,a special suffix is used. For the aldehyde group $(-CHO)$ attached to a ring,the suffix 'carbaldehyde' is used instead of 'al'. The hydroxyl group $(-OH)$ is treated as a substituent and is given the prefix 'hydroxy'. Numbering starts from the carbon attached to the $-CHO$ group,giving the $-OH$ group the position $2$. Thus,the name is $2-$hydroxycyclopentanecarbaldehyde.
220
MediumMCQ
Which of the following compounds is $2,2,3-$trimethylhexane?
A
$CH_3C(CH_3)_2CH_2CH_2CH(CH_3)_2$
B
$CH_3C(CH_3)_2CH(CH_3)CH_2CH_2CH_3$
C
$CH_3CH_2CH(CH_3)C(CH_3)_2CH_2CH_3$
D
$CH_3C(CH_3)_2CH(CH_3)CH_2CH_2CH_3$

Solution

(D) To identify $2,2,3-$trimethylhexane,we look for a hexane chain ($6$ carbons) with methyl groups at positions $2, 2,$ and $3$.
$1$. The parent chain is hexane $(C_6)$.
$2$. At position $2$,there are two methyl groups: $CH_3-C(CH_3)_2-$.
$3$. At position $3$,there is one methyl group: $-CH(CH_3)-$.
$4$. The remaining chain is $-CH_2-CH_2-CH_3$.
Combining these,the structure is $CH_3-C(CH_3)_2-CH(CH_3)-CH_2-CH_2-CH_3$.
This corresponds to option $D$.
221
DifficultMCQ
Write the $IUPAC$ name of the given compound.
Question diagram
A
$3, 3'-$Dichloro$-1, 1'-$bicyclobutane
B
$1, 6-$Dichloro cyclo(dibutane)
C
Bis$(3-$chlorocyclobutane$)$
D
$1-$Chloro$-3-(3'-$chloro$)$ cyclobutane

Solution

(A) The given structure consists of two cyclobutane rings connected by a single bond between the $1$ and $1'$ positions.
Each ring has a chlorine atom attached at the $3$ and $3'$ positions respectively.
According to $IUPAC$ nomenclature for bicyclic systems where two identical rings are joined by a single bond,the name is derived by using the prefix 'bis' or by numbering the rings as $1, 1'$.
Thus,the correct name is $3, 3'-$dichloro$-1, 1'-$bicyclobutane.
222
MediumMCQ
What is the $IUPAC$ name of the compound $CH_3-C(C_2H_5)=CHCH_3$?
A
$2-$ethylbut$-2-$ene
B
$2-$ethylbut$-2-$ene
C
$3-$methylpent$-2-$ene
D
$3-$ethylbut$-2-$ene

Solution

(C) $1$. Identify the longest carbon chain containing the double bond. The structure is $CH_3-C(CH_2CH_3)=CHCH_3$.
$2$. The longest chain has $5$ carbon atoms,so the parent alkane is pentane.
$3$. Number the chain from the end closer to the double bond: $C_1H_3-C_2(C_2H_5)=C_3H-C_4H_2-C_5H_3$ is incorrect; the correct numbering is $CH_3(1)-C(2)(C_2H_5)=CH(3)-CH_2(4)-CH_3(5)$ is not right.
$4$. Let's re-examine: $CH_3-C(CH_2CH_3)=CH-CH_3$. The longest chain is $5$ carbons long. Numbering from right to left: $CH_3(1)-CH(2)=C(3)(CH_2CH_3)-CH_3(4)$ is wrong.
$5$. Correct numbering: $CH_3(1)-CH(2)=C(3)(CH_2CH_3)-CH_3$ is not it. The structure is $CH_3-C(CH_2CH_3)=CH-CH_3$. The longest chain is $CH_3-C(=CH-CH_3)-CH_2-CH_3$. This is a $5$-carbon chain.
$6$. Numbering: $CH_3(1)-CH(2)=C(3)(CH_3)-CH_2(4)-CH_3(5)$ is wrong. The structure is $CH_3-C(C_2H_5)=CH-CH_3$. The longest chain is $CH_3-CH_2-C(CH_3)=CH-CH_3$. This is $3-$methylpent$-2-$ene.
223
MediumMCQ
What is the $IUPAC$ name of the compound $H_2N-CH(COOH)-CH(COOH)-CHO$?
A
$3-$amino$-2-$formylbutane$-1,4-$dioic acid
B
$2-$amino$-2,3-$dicarboxypropanal
C
$2-$amino$-3-$formylbutane$-1,4-$dioic acid
D
$1-$amino$-2-$formylsuccinic acid

Solution

(C) $1$. Identify the principal functional group. The carboxylic acid $(-COOH)$ group has higher priority than the aldehyde $(-CHO)$ and amine $(-NH_2)$ groups.
$2$. Select the longest carbon chain containing the principal functional groups. The chain consists of $4$ carbons,making it a butane derivative.
$3$. Number the chain starting from the end that gives the lowest locants to the substituents. Numbering from the left gives the $-COOH$ at $C-1$ and $C-4$,the $-NH_2$ at $C-2$,and the $-CHO$ at $C-3$.
$4$. The name is constructed as $2-$amino$-3-$formylbutane$-1,4-$dioic acid.
224
MediumMCQ
What is the $IUPAC$ name of $CH_3 - C \equiv C - C(CH_3)_3$?
A
$2,2$-dimethylpent-$3$-yne
B
$t$-butylpropyne
C
$4,4$-dimethylpent-$2$-yne
D
$1,3,3,3$-tetramethylethyne

Solution

(C) To determine the $IUPAC$ name of the given compound $CH_3 - C \equiv C - C(CH_3)_3$:
$1$. Identify the longest carbon chain containing the triple bond.
$2$. Number the chain starting from the end that gives the triple bond the lowest possible locant.
$3$. The structure is $CH_3 - C \equiv C - C(CH_3)_3$,which can be expanded as $CH_3 - C \equiv C - C(CH_3)_2 - CH_3$.
$4$. The longest chain has $5$ carbons (pentane derivative).
$5$. The triple bond starts at position $2$ when numbered from left to right.
$6$. There are two methyl groups at position $4$.
$7$. Thus,the name is $4,4$-dimethylpent-$2$-yne.
225
MediumMCQ
Give the $IUPAC$ name of the following compound.
Question diagram
A
$trans-2-chloro-3-iodo-2-pentene$
B
$cis-2-chloro-3-iodo-2-pentene$
C
$trans-3-iodo-4-chloro-3-pentene$
D
$cis-3-iodo-4-chloro-3-pentene$

Solution

(A) $1$. Identify the longest carbon chain containing the double bond,which is a $pentene$ chain.
$2$. Number the chain to give the double bond the lowest possible position. The double bond starts at carbon $2$,so it is a $pent-2-ene$ derivative.
$3$. Identify substituents: $chloro$ at position $2$ and $iodo$ at position $3$.
$4$. Determine the configuration ($E/Z$ or $cis/trans$): On carbon $2$,the priority group is $Cl$ $(Z=17)$ over $CH_3$ $(Z=6)$. On carbon $3$,the priority group is $I$ $(Z=53)$ over $CH_2CH_3$ $(Z=6)$.
$5$. Since the higher priority groups ($Cl$ and $I$) are on opposite sides of the double bond,the configuration is $trans$ (or $E$).
$6$. Combining these,the name is $trans-2-chloro-3-iodo-2-pentene$.
226
MediumMCQ
Provide the $IUPAC$ name for the compound: $CH_3-CH(COOH)-CH_2-CH(COOH)-CH(CH_3)-COOH$.
A
$2,4,5-$hexanetricarboxylic acid
B
$2,3,5-$hexanetricarboxylic acid
C
$2-(1-$carboxyethyl$)-4-4-$methylpentanedioic acid
D
$3,5-$dicarboxy$-2-$methylhexanoic acid

Solution

(B) $1$. Identify the longest carbon chain containing the maximum number of principal functional groups (carboxylic acid groups). The longest chain containing all three $-COOH$ groups is a $6-$carbon chain (hexane).
$2$. Number the chain starting from the end that gives the lowest locants to the substituents and functional groups.
$3$. Numbering from the right: $C1$ $(-COOH)$,$C2$ $(-CH(CH_3)-)$,$C3$ $(-CH(COOH)-)$,$C4$ $(-CH_2-)$,$C5$ $(-CH(COOH)-)$,$C6$ $(-CH_3)$.
$4$. The substituents are at positions $2, 3,$ and $5$.
$5$. The correct $IUPAC$ name is $2,3,5-$hexanetricarboxylic acid.
227
EasyMCQ
What is the $IUPAC$ name of the compound $CH_2=CH-CH_2-Cl$?
A
Allyl chloride
B
$1$-Chloro-$3$-propene
C
$3$-Chloro-$1$-propene
D
Vinyl chloride

Solution

(C) The given compound is $CH_2=CH-CH_2-Cl$.
To name it according to $IUPAC$ rules,we identify the longest carbon chain containing the double bond.
The chain has $3$ carbon atoms,so the parent alkane is propane.
Numbering starts from the end closer to the double bond,giving the double bond position $1$.
Thus,the suffix is $-1$-propene.
The chlorine atom is attached to the $3^{rd}$ carbon atom.
Therefore,the $IUPAC$ name is $3$-chloro-$1$-propene.
228
MediumMCQ
Provide the $IUPAC$ name of the given compound.
Question diagram
A
$3, 3-$diethyl$-2, 2-$dimethylpentane
B
$4, 4-$dimethyl$-5, 5-$diethylpentane
C
$5, 5-$dimethyl$-4, 4-$dimethylpentane
D
$3-$ethyl$-4, 4-$dimethylheptane

Solution

(D) $1$. Identify the longest carbon chain. The longest chain contains $7$ carbon atoms,so the parent alkane is heptane.
$2$. Number the chain from the end that gives the substituents the lowest possible locants. Numbering from left to right gives substituents at positions $3, 4, 4$. Numbering from right to left gives substituents at positions $4, 4, 5$.
$3$. The substituents are an ethyl group at position $3$ and two methyl groups at position $4$.
$4$. Combining these,the $IUPAC$ name is $3-$ethyl$-4, 4-$dimethylheptane.
229
MediumMCQ
What is the $IUPAC$ name of the given compound?
Question diagram
A
Propylene oxide
B
$1, 2-$Epoxypropane
C
$1, 2-$Ethoxypropane
D
$1, 2-$Propoxide

Solution

(B) The given structure is a three-membered cyclic ether,which is known as an epoxide or oxirane.
In $IUPAC$ nomenclature,such compounds are named as epoxy derivatives of the corresponding alkane.
The parent chain consists of $3$ carbon atoms,so it is a propane derivative.
The oxygen atom is bonded to carbon atoms $1$ and $2$.
Therefore,the $IUPAC$ name is $1, 2-$epoxypropane.
230
MediumMCQ
What is the $IUPAC$ name of the compound $CH_3-CO-CH_2-CH(OH)-CHO$?
A
$5-hydroxy-4-oxopentanal$
B
$4-hydroxy-2-oxopentanal$
C
$2-hydroxy-4-oxopentanal$
D
$4-hydroxy-5-oxopentanal$

Solution

(C) $1$. Identify the principal functional group: The compound contains an aldehyde $(-CHO)$ and a ketone $(-CO-)$ group. According to $IUPAC$ priority rules,the aldehyde group has higher priority than the ketone group. Therefore,the parent chain is named as an $alkanal$.
$2$. Number the carbon chain: Start numbering from the aldehyde carbon as $C-1$. The chain is $C_1(CHO)-C_2(CHOH)-C_3(CH_2)-C_4(CO)-C_5(CH_3)$.
$3$. Identify substituents: There is a hydroxyl group $(-OH)$ at position $2$ and a ketone group $(-CO-)$ at position $4$. In $IUPAC$ nomenclature,the ketone group is treated as a substituent named '$oxo$' when an aldehyde is the principal functional group.
$4$. Combine the parts: The name is $2-hydroxy-4-oxopentanal$.
231
MediumMCQ
Which of the following $IUPAC$ names is incorrect?
A
$CH_3-C(=O)-CH(CH_3)_2$: $2$-methylbutan-$3$-one
B
$CH_3-CH(CH_3)-CH(CH_3)-CH_2-CH_3$: $2,3$-dimethylpentane
C
$CH_3-C \equiv C-CH(CH_3)_2$: $4$-methylpent-$2$-yne
D
$CH_3-CH(Cl)-CH(Br)-CH_3$: $2$-bromo-$3$-chlorobutane

Solution

(A) Let us analyze each option:
$A$. The structure $CH_3-C(=O)-CH(CH_3)_2$ is $3$-methylbutan-$2$-one,not $2$-methylbutan-$3$-one. The numbering should start from the end closer to the ketone group.
$B$. The structure $CH_3-CH(CH_3)-CH(CH_3)-CH_2-CH_3$ is correctly named $2,3$-dimethylpentane.
$C$. The structure $CH_3-C \equiv C-CH(CH_3)_2$ is correctly named $4$-methylpent-$2$-yne.
$D$. The structure $CH_3-CH(Cl)-CH(Br)-CH_3$ is named alphabetically as $3$-bromo-$2$-chlorobutane,not $2$-bromo-$3$-chlorobutane. However,in many contexts,option $A$ is the most fundamentally incorrect due to the numbering priority of the functional group.
232
MediumMCQ
Give the $IUPAC$ name of the given compound.
Question diagram
A
$1, 1-$dimethyl$-3-$cyclohexanol
B
$1, 1-$dimethyl$-3-$hydroxycyclohexane
C
$3, 3-$dimethyl$-1-$cyclohexanol
D
$3, 3-$dimethyl$-1-$hydroxycyclohexane

Solution

(C) $1$. Identify the principal functional group: The $-OH$ group is the principal functional group,so the suffix is $-ol$.
$2$. Number the ring: The carbon atom attached to the $-OH$ group is assigned position $1$. To give the substituents (methyl groups) the lowest possible locants,we number the ring in the direction that assigns them position $3$. Thus,the methyl groups are at position $3$.
$3$. Assemble the name: The parent chain is cyclohexane. With the $-OH$ group at position $1$ and two methyl groups at position $3$,the name is $3, 3-$dimethylcyclohexan$-1-$ol,which is commonly written as $3, 3-$dimethylcyclohexanol.
233
DifficultMCQ
Write the $IUPAC$ name of the given compound.
Question diagram
A
Methyl $2,2$-acetyl ethanoate
B
$2,2$-Diacetyl-$1$-methoxy ethanone
C
Methyl $2$-acetyl-$3$-oxobutanoate
D
None of these

Solution

(C) The structure is $CH_3-CO-CH(COCH_3)-COOCH_3$.
$1$. Identify the principal functional group: The ester group $(-COOCH_3)$ has higher priority than the ketone group $(-CO-)$. Thus,the parent chain is a butanoate.
$2$. Number the chain starting from the ester carbon as $C-1$.
$3$. The chain is $C_1(O)-C_2(H)(COCH_3)-C_3(=O)-C_4(H_3)$.
$4$. At $C-2$,there is an acetyl group $(-COCH_3)$.
$5$. At $C-3$,there is a ketone group $(-=O)$.
$6$. The $IUPAC$ name is Methyl $2$-acetyl-$3$-oxobutanoate.
234
MediumMCQ
Which of the following is an incorrect $IUPAC$ name?
A
$CH_3CH_2CH_2COOCH_2CH_3$ (Ethyl butanoate)
B
$CH_3CH(CH_3)CH_2CHO$ ($3$-Methylbutanal)
C
$CH_3CH(OH)CH(CH_3)CH_3$ ($2$-Methyl$-3-$butanol)
D
$CH_3CH(CH_3)COCH_2CH_3$ ($2$-Methyl$-3-$pentanone)

Solution

(C) Let us analyze each option:
$A$: $CH_3CH_2CH_2COOCH_2CH_3$ is an ester. The alkyl group attached to oxygen is ethyl,and the acid part is butanoate. The name $Ethyl \ \text{butanoate}$ is correct.
$B$: $CH_3CH(CH_3)CH_2CHO$. The longest chain has $4$ carbons. The methyl group is at position $3$. The name $3-\text{Methylbutanal}$ is correct.
$C$: $CH_3CH(OH)CH(CH_3)CH_3$. Numbering should start from the end closer to the functional group $(-OH)$. Numbering from left: $CH_3(1)-CH(OH)(2)-CH(CH_3)(3)-CH_3(4)$. The correct name is $3-\text{Methylbutan-2-ol}$. The given name $2-\text{Methyl-3-butanol}$ is incorrect.
$D$: $CH_3CH(CH_3)COCH_2CH_3$. Numbering from left: $CH_3(1)-CH(CH_3)(2)-CO(3)-CH_2(4)-CH_3(5)$. The correct name is $2-\text{Methylpentan-3-one}$. The given name $2-\text{Methyl-3-pentanone}$ is correct.
235
MediumMCQ
Provide the $IUPAC$ name of the given compound.
Question diagram
A
$3-(2-\text{methylpropyl})-1-\text{hepten}-4-\text{yne}$
B
$\text{oct}-1-\text{en}-4-\text{yne}$
C
$4-\text{methyl}-2-\text{pentyne}$
D
$3, 3, 4-\text{trimethyl}-1-\text{hexyne}$

Solution

(B) $1$. Identify the longest carbon chain containing both the double and triple bonds. The chain has $8$ carbon atoms,so the parent alkane is octane.
$2$. Number the chain from the end that gives the lowest locants to the multiple bonds. Numbering from left to right gives the double bond at position $1$ and the triple bond at position $4$.
$3$. The name is constructed as $\text{oct}-1-\text{en}-4-\text{yne}$.
$4$. Thus,the correct $IUPAC$ name is $\text{oct}-1-\text{en}-4-\text{yne}$.
236
MediumMCQ
Give the correct $IUPAC$ name of the compound shown in the image.
Question diagram
A
$1,2-$dicyanoethene
B
but$-2-$ene$-1,4-$dinitrile
C
di but$-2-$ene$-1,4-$nitrile
D
none of these

Solution

(B) The given structure is $NC-CH=CH-CN$.
$1$. Identify the longest carbon chain containing the principal functional groups. The longest chain has $4$ carbon atoms.
$2$. The principal functional group is the nitrile group $(-CN)$. Since there are two nitrile groups at the ends,the chain is numbered starting from one of the nitrile carbons as $1$ and $4$.
$3$. The double bond is located between carbon $2$ and $3$.
$4$. The parent chain is a butane derivative with a double bond,so it is a but$-2-$ene derivative.
$5$. The nitrile groups are at positions $1$ and $4$,so the suffix is $1,4-$dinitrile.
$6$. Combining these,the correct $IUPAC$ name is but$-2-$ene$-1,4-$dinitrile.
237
EasyMCQ
Pyrogallol is a ...... trihydroxybenzene.
A
$1, 2, 4$
B
$1, 2, 3$
C
$1, 3, 5$
D
None of these.

Solution

(B) Pyrogallol is the common name for $1, 2, 3$-trihydroxybenzene.
It consists of a benzene ring with three hydroxyl $(-OH)$ groups attached at the $1, 2,$ and $3$ positions.
238
MediumMCQ
What is vinyl carbinol among the following?
A
$CH_2=CH-CH_2OH$
B
$CH_3C(OH)=CH_2$
C
$CH_3-CH=CH-OH$
D
$CH_3-C(CH_2OH)=CH_2$

Solution

(A) The term $Carbinol$ is used for methanol $(CH_3OH)$.
When one hydrogen atom of the methyl group in methanol is replaced by a vinyl group $(CH_2=CH-)$,it is called vinyl carbinol.
The structure of vinyl carbinol is $CH_2=CH-CH_2OH$ (also known as allyl alcohol,but in the context of carbinol nomenclature,it is vinyl carbinol).
Therefore,the correct structure is $CH_2=CH-CH_2OH$.
239
MediumMCQ
What is the $IUPAC$ name of $CH_3COCH(CH_3)_2$?
A
$4-$Methyl iso-propyl ketone
B
$3-$Methyl$-2-$butanone
C
Iso-propyl methyl ketone
D
$2-$Methyl$-3-$butanone

Solution

(B) The structure of the given compound is $CH_3-CO-CH(CH_3)_2$.
To name it according to $IUPAC$ rules,we identify the longest carbon chain containing the ketone group.
The chain has $4$ carbon atoms,so the parent alkane is butane.
The ketone group is at position $2$,and there is a methyl group at position $3$.
Thus,the name is $3-$methyl$-2-$butanone.
240
MediumMCQ
What is the $IUPAC$ name of the following compound?
$HOOC-CH_2-CH(COOH)-CH_2-CH_2-COOH$
A
$2-(\text{carboxymethyl})\text{pentane}-1,5-\text{dioic acid}$
B
$3-\text{carboxyhexane}-1,6-\text{dioic acid}$
C
$\text{Propane}-1,2,3-\text{tricarboxylic acid}$
D
$4-\text{carboxyhexane}-1,6-\text{dioic acid}$

Solution

(C) The structure is $HOOC-CH_2-CH(COOH)-CH_2-CH_2-COOH$.
To name this compound according to $IUPAC$ rules,we select the longest carbon chain containing the maximum number of principal functional groups.
Here,the longest chain containing the three carboxylic acid groups is a $5$-carbon chain (pentane).
The carboxylic acid groups are at positions $1, 2,$ and $5$.
Thus,the name is $\text{Propane}-1,2,3-\text{tricarboxylic acid}$ is incorrect based on the chain length; the correct name is $\text{Pentane}-1,2,5-\text{tricarboxylic acid}$ or more commonly named as $\text{Propane}-1,2,3-\text{tricarboxylic acid}$ derivative. However,looking at the options provided,the structure corresponds to $\text{Propane}-1,2,3-\text{tricarboxylic acid}$ if we consider the backbone correctly. Given the options,the intended answer is $C$.
241
MediumMCQ
What is the $IUPAC$ name of the compound: $CH_3-CH_2-CH(CH_3)-CH_2-COCl$?
A
$3-$Methylpentanoyl chloride
B
$3-$Methylbutanoyl chloride
C
$1-$Chloro$-3-$ethylbutanol
D
$1-$Chloro$-3-$methylpentanone

Solution

(A) The structure is $CH_3-CH_2-CH(CH_3)-CH_2-COCl$.
To name this compound according to $IUPAC$ rules:
$1$. Identify the principal functional group,which is the acyl chloride $(-COCl)$. The carbon of the $-COCl$ group is assigned position $1$.
$2$. Select the longest carbon chain containing the functional group. The chain has $5$ carbons,so the parent alkane is pentane.
$3$. The suffix for acyl chloride is 'oyl chloride'. Thus,the parent name is pentanoyl chloride.
$4$. Identify the substituent: there is a methyl group $(-CH_3)$ at position $3$.
$5$. Combining these,the name is $3-$methylpentanoyl chloride.
242
DifficultMCQ
$IUPAC$ name for the compound
Question diagram
A
trans $3$-iodo,$4$-chloro,$pent-3$-ene
B
cis $3$-chloro,$3$-iodo,$pent-2$-ene
C
trans $2$-chloro,$3$-iodo,$pent-2$-ene
D
cis $3$-iodo,$4$-chloro,$pent-3$-ene

Solution

(C) $1$. Identify the longest carbon chain containing the double bond. The chain has $5$ carbons,so the parent alkane is $pentane$,and the alkene is $pent-2$-ene.
$2$. Number the chain to give the double bond the lowest possible locant. Numbering from left to right gives the double bond at position $2$.
$3$. Substituents are $chloro$ at position $2$ and $iodo$ at position $3$.
$4$. Determine the configuration: The high-priority groups ($Cl$ on $C-2$ and $CH_2CH_3$ on $C-3$) are on opposite sides of the double bond,which corresponds to the $trans$ configuration.
$5$. Combining these,the name is $trans-2-chloro-3-iodopent-2-ene$.
243
EasyMCQ
The $IUPAC$ name of the following structure is $CH_3-C(=O)-CH_2-COOH$.
A
$3$-oxobutanoic acid
B
$2$-oxobutanoic acid
C
$4$-oxobutanoic acid
D
$3$-oxopropanoic acid

Solution

(A) The structure is $CH_3-C(=O)-CH_2-COOH$.
$1$. Identify the principal functional group: The carboxylic acid group $(-COOH)$ has higher priority than the ketone group $(=O)$.
$2$. Number the carbon chain starting from the carboxylic acid carbon as $C-1$: $C^{(1)}OOH - C^{(2)}H_2 - C^{(3)}(=O) - C^{(4)}H_3$.
$3$. Identify substituents: There is an oxo group at position $3$.
$4$. Combine the parts: The parent chain has $4$ carbons (butanoic acid) with an oxo group at position $3$,resulting in $3$-oxobutanoic acid.
244
MediumMCQ
The $IUPAC$ name of the compound $CH_3-CH_2-CH(O)-CH_2$ is:
A
$1, 2-$epoxybutane
B
Ethyl methyl ether
C
Keto pentanone
D
None of these

Solution

(A) The given compound $CH_3-CH_2-CH(O)-CH_2$ contains a three-membered ring with two carbon atoms and one oxygen atom,which is known as an epoxide or oxirane ring.
In $IUPAC$ nomenclature,such compounds are named as epoxyalkanes.
The numbering starts from the carbon attached to the oxygen to give the lowest possible locants.
Thus,the $IUPAC$ name is $1, 2-$epoxybutane.
245
MediumMCQ
The $IUPAC$ name of $CH_3-CH_2-C(CH_2CH_3)_2-CH(CH_3)-CH_2-CH_2-CH_2-CH_3$ is
A
$2, 2-$ diethyl-$5-$ methyldecane
B
$3, 3-$ diethyl-$5-$ methyldecane
C
$3, 3-$ diethyl-$5-$ methylhexane
D
$3, 3-$ diethyl-$4-$ methyloctane

Solution

(D) The longest carbon chain in the given structure $CH_3-CH_2-C(CH_2CH_3)_2-CH(CH_3)-CH_2-CH_2-CH_2-CH_3$ contains $8$ carbon atoms,so the parent alkane is octane.
Numbering the chain from the left side gives the substituents (two ethyl groups at position $3$ and one methyl group at position $4$) the lowest possible locants.
According to alphabetical order,ethyl comes before methyl.
Therefore,the $IUPAC$ name is $3,3-diethyl-4-methyloctane$.
246
MediumMCQ
The $IUPAC$ name for $CH_3CH(OH)CH_2-C(CH_3)_2OH$ is
A
$1,1-$dimethyl$-1,3-$butanediol
B
$2-$methyl$-2,4-$pentanediol
C
$4-$methyl$-2,4-$pentanediol
D
$1,3,3-$trimethyl$-1,3-$propanediol

Solution

(B) The given structure is $CH_3-CH(OH)-CH_2-C(CH_3)_2OH$.
To determine the $IUPAC$ name,we select the longest carbon chain containing the functional groups (hydroxyl groups).
The chain has $5$ carbons,so the parent alkane is pentane.
Numbering the chain from the end that gives the lowest locants to the substituents and functional groups:
Starting from the right,the hydroxyl groups are at positions $2$ and $4$,and the methyl group is at position $2$.
Thus,the name is $2-$methyl$-2,4-$pentanediol.
247
MediumMCQ
Choose the correct $IUPAC$ name of the compound $CH_3-CH(CH_3)-CH(CH_3)-C\equiv C-CH_3$.
A
$2,3-$dimethyl-$4-$hexyne
B
$4,5-$dimethyl-$2-$hexyne
C
$5-$propyl-$2-$pentyne
D
$2-$propyl-$3-$pentyne

Solution

(B) To name the compound $CH_3-CH(CH_3)-CH(CH_3)-C\equiv C-CH_3$ according to $IUPAC$ rules:
$1$. Identify the longest carbon chain containing the triple bond. The chain has $6$ carbons,so the parent alkane is $hexane$.
$2$. Number the chain from the end that gives the triple bond the lowest possible locant. Numbering from right to left,the triple bond starts at carbon $2$.
$3$. Identify the substituents: there are two methyl groups at positions $4$ and $5$.
$4$. Combining these,the name is $4,5-$dimethyl-$2-$hexyne.
248
DifficultMCQ
The $IUPAC$ name of the compound is . . . . . . .
Question diagram
A
$5-$formylhex$-2-$en$-3-$one
B
$5-$methyl$-4-$oxohex$-2-$en$-5-$al
C
$3-$keto$-2-$methylhex$-5-$enal
D
$2-$methyl$-3-$oxohex$-4-$enal

Solution

(D) $1$. Identify the principal functional group: The aldehyde $(-CHO)$ group has higher priority than the ketone $(>C=O)$ group. Thus,the parent chain must include the aldehyde carbon as $C-1$.
$2$. Number the chain: Start numbering from the aldehyde carbon $(C-1)$. The chain is $6$ carbons long $(hex)$.
$3$. Identify substituents and unsaturation: There is a methyl group at $C-2$,a ketone group at $C-3$,and a double bond starting at $C-4$.
$4$. Combine the parts: The name is $2-$methyl$-3-$oxohex$-4-$enal.
249
EasyMCQ
The structure of the isobutyl group in an organic compound is:
A
$CH_3-CH_2-CH_2-CH_2-$
B
$CH_3-C(CH_3)_2-$
C
$CH_3-CH(CH_3)-CH_2-$
D
$CH_3-CH_2-CH(CH_3)-$

Solution

(C) The isobutyl group is a four-carbon alkyl group with a methyl branch at the second carbon from the end of the chain.
Its structure is $CH_3-CH(CH_3)-CH_2-$.
250
DifficultMCQ
The structure of the compound whose $IUPAC$ name is $3-$ethyl$-2-$hydroxy$-4-$methylhex$-3-$en$-5-$ynoic acid is:
A
Option A
B
Option B
C
Option C
D
Option D

Solution

(D) To determine the structure of $3-$ethyl$-2-$hydroxy$-4-$methylhex$-3-$en$-5-$ynoic acid,we follow these steps:
$1$. The parent chain is a hexenoic acid,meaning it has $6$ carbon atoms with a carboxylic acid group at $C-1$.
$2$. The suffix $-3-$en$-5-$ynoic acid indicates a double bond at $C-3$ and a triple bond at $C-5$.
$3$. The substituents are an ethyl group at $C-3$,a hydroxy group at $C-2$,and a methyl group at $C-4$.
$4$. Constructing the chain: $CH_3-C\equiv C-C(CH_3)=C(C_2H_5)-CH(OH)-COOH$.
$5$. Comparing this with the given options,the structure corresponding to this $IUPAC$ name is represented in option $D$.

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