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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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451
DifficultMCQ
The $IUPAC$ name of $CH_3CH_2OCH(CH_3)_2$ is
A
Isopropoxyethane
B
$2-$Methoxybutane
C
$1-$Methyl$-1-$methoxyethane
D
$2-$Ethoxypropane

Solution

(D) The given compound is $CH_3CH_2OCH(CH_3)_2$.
In $IUPAC$ nomenclature for ethers,the smaller alkyl group is treated as an alkoxy substituent attached to the longer alkane chain.
Here,the ethoxy group $(-OCH_2CH_3)$ is attached to the second carbon of the propane chain.
Therefore,the correct $IUPAC$ name is $2-$ethoxypropane.
452
MediumMCQ
The $IUPAC$ nomenclature of $CH_3-C(CH_3)_2-CH=C(CH_3)_2$ is
A
$2,4,4-Trimethylpent-3-ene$
B
$2,4,4-Trimethylpent-2-ene$
C
$2,2,4-Trimethylpent-3-ene$
D
$2,2,4-Trimethylpent-2-ene$

Solution

(B) The given structure is $CH_3-C(CH_3)_2-CH=C(CH_3)_2$.
To determine the $IUPAC$ name,we identify the longest carbon chain containing the double bond.
Numbering the chain from the end closer to the double bond (right to left) gives the double bond position at $C-2$.
The methyl groups are located at positions $2, 4,$ and $4$.
Thus,the correct $IUPAC$ name is $2,4,4-Trimethylpent-2-ene$.
453
AdvancedMCQ
The $IUPAC$ name of the given compound is:
Question diagram
A
$2-$hydroxymethyl benzoate
B
$2-$hydroxyethyl benzoate
C
Methyl $3-$hydroxybenzoate
D
$1-$hydroxymethyl benzoate

Solution

(C) $1$. Identify the principal functional group: The ester group $(-COOCH_3)$ has higher priority than the hydroxyl group $(-OH)$. Therefore,the parent chain is a benzoate ester.
$2$. Number the ring: The carbon atom of the benzene ring attached to the ester group is assigned position $1$.
$3$. Locate substituents: The hydroxyl group $(-OH)$ is attached to the carbon at position $3$ of the benzene ring.
$4$. Name the compound: The ester part is 'methyl' and the substituted benzene ring is '$3$-hydroxybenzoate'. Combining these,the $IUPAC$ name is Methyl $3-$hydroxybenzoate.
454
DifficultMCQ
What is the $IUPAC$ name of the given compound? $CH_2=CH-O-CHO$
A
Ethenyl formate
B
Vinyl methanoate
C
Ethenyl methanoate
D
Ethenyloxymethanoate

Solution

(C) The given structure is $CH_2=CH-O-CHO$.
This is an ester of formic acid $(HCOOH)$ and vinyl alcohol $(CH_2=CHOH)$.
In $IUPAC$ nomenclature for esters,the alkyl group attached to the oxygen is named first,followed by the name of the acid part with the suffix $-oate$.
The alkyl group is $CH_2=CH-$,which is called 'ethenyl' (or 'vinyl').
The acid part is $HCOO-$,which is derived from methanoic acid,so it is named 'methanoate'.
Combining these,the $IUPAC$ name is 'ethenyl methanoate'.
455
DifficultMCQ
Which of the following $IUPAC$ names is incorrect?
A
Option A
B
Option B
C
Option C
D
Option D

Solution

(B) According to $IUPAC$ nomenclature rules for cyclic compounds containing a double bond,the double bond carbons must be assigned positions $1$ and $2$ such that the substituents get the lowest possible locants.
$A$: In $3,6$-dimethylcyclohexene,the double bond is between $C1$ and $C2$. If we number the ring starting from the double bond,the substituents are at positions $3$ and $6$. This is correct.
$B$: In $1,6$-dimethylcyclohexene,the double bond is between $C1$ and $C2$. If we number the ring starting from the double bond,the substituents are at positions $1$ and $6$. This is correct.
$C$: In $6,6$-dimethylcyclohexene,the double bond is between $C1$ and $C2$. If we number the ring starting from the double bond,the substituents are at position $6$. This is correct.
$D$: In $1,5$-dimethylcyclohexene,the double bond is between $C1$ and $C2$. If we number the ring starting from the double bond,the substituents are at positions $1$ and $5$. This is correct.
Wait,let us re-evaluate the numbering for $B$. In $1,6$-dimethylcyclohexene,if we number the double bond as $1$ and $2$,the substituents are at $1$ and $6$. However,if we number in the other direction,we could get $1,2$-dimethylcyclohexene. Actually,for $B$,the structure shows a methyl group on one of the double-bonded carbons $(C1)$ and another methyl group on the adjacent carbon $(C6)$. This is correctly named $1,6$-dimethylcyclohexene.
Let us re-evaluate $A$: $3,6$-dimethylcyclohexene. If we number the double bond as $1,2$,the substituents are at $3$ and $6$. This is correct.
Actually,all these names follow the rules. Let us check if any structure is misnamed. In $B$,the structure is $1,6$-dimethylcyclohexene. This is correct. In $A$,$3,6$-dimethylcyclohexene is correct. In $C$,$6,6$-dimethylcyclohexene is correct. In $D$,$1,5$-dimethylcyclohexene is correct.
Upon closer inspection of standard $IUPAC$ rules,the numbering should be such that the sum of locants is minimized. For $B$,$1,6$-dimethylcyclohexene,the locants are $1,6$. If we number the other way,it is $1,2$-dimethylcyclohexene. Since $1,2 < 1,6$,the name $1,6$-dimethylcyclohexene is incorrect and should be $1,2$-dimethylcyclohexene.
456
DifficultMCQ
Number of functional groups present in the following compound is
Question diagram
A
$5$
B
$7$
C
$6$
D
$8$

Solution

(C) The functional groups present in the given compound are:
$1$. Aldehyde $(-CHO)$
$2$. Amine $(-NH_2)$
$3$. Ketone $(>C=O)$
$4$. Amide $(-CONH-)$
$5$. Carboxylic acid $(-COOH)$
$6$. Acid anhydride $(-CO-O-CO-)$
Thus,there are $6$ distinct functional groups present in the molecule.
457
AdvancedMCQ
Identify the structure of $5-(2,2-\text{dimethylpropyl})\text{nonane}$.
A
$CH_3-CH(CH_3)-C(CH_3)_2-CH(C_4H_9)-C_2H_5$
B
$CH_3-CH(CH_3)-CH(C_4H_9)-CH(CH_3)-C_3H_7$
C
$CH_3-C(CH_3)_2-CH_2-CH(C_4H_9)-C_4H_9$
D
$CH_3-CH(CH_3)-CH(C_4H_9)-CH(C_2H_5)-CH_3$

Solution

(C) The parent chain is nonane,which contains $9$ carbon atoms.
At the $5^{th}$ position,there is a $2,2-\text{dimethylpropyl}$ group (also known as a neopentyl group).
The structure consists of a $9$-carbon chain with a substituent at the $5^{th}$ carbon.
The substituent is $-CH_2-C(CH_3)_3$.
Thus,the full structure is $CH_3-CH_2-CH_2-CH_2-CH(CH_2-C(CH_3)_3)-CH_2-CH_2-CH_2-CH_3$,which can be written as $CH_3-C(CH_3)_2-CH_2-CH(C_4H_9)-C_4H_9$.
458
DifficultMCQ
Which of the following is a correct $IUPAC$ name?
A
$4-(1, 1-$dimethylethyl$)-2-$methylpentane
B
$1-$aminobutan$-1-$one
C
$2-$ethyl$-3-$methylpentane
D
$3-$ethyl$-2-$methylpentane

Solution

(D) To determine the correct $IUPAC$ name,we must identify the longest carbon chain and number it such that substituents get the lowest possible locants.
$1$. For option $A$: The structure $4-(1, 1-$dimethylethyl$)-2-$methylpentane corresponds to a chain that is not the longest. The longest chain would be a heptane derivative.
$2$. For option $B$: $1-$aminobutan$-1-$one is not a valid $IUPAC$ name for the structure shown (which is butanamide).
$3$. For option $C$: $2-$ethyl$-3-$methylpentane is incorrect because the longest chain is actually a hexane chain ($3, 4-$dimethylhexane).
$4$. For option $D$: $3-$ethyl$-2-$methylpentane is a correct $IUPAC$ name for the structure shown in the image,as it correctly identifies the longest chain (pentane) and the positions of the substituents ($2-$methyl and $3-$ethyl).
459
EasyMCQ
The number of carbon atoms in the longest chain during the $IUPAC$ nomenclature of the following compound is:
Question diagram
A
$8$
B
$7$
C
$6$
D
$5$

Solution

(A) To determine the longest chain for $IUPAC$ nomenclature,we must include the principal functional group (ketone) and the double bond if possible.
Starting from the right end to give the ketone the lowest possible locant,the numbering is as follows:
$1$ (terminal $CH_3$),$2$ $(CH_2)$,$3$ $(C=O)$,$4$ $(CH_2)$,$5$ $(CH_2)$,$6$ $(C=)$,$7$ $(CH)$,$8$ $(CH_3)$.
The longest carbon chain contains $8$ carbon atoms.
460
DifficultMCQ
The $IUPAC$ name of the following compound is
Question diagram
A
$3-$cyano$-5-$hydroxycyclohex$-5-$enoic acid
B
$3-$cyano$-5-$hydroxycyclohex$-5-$enecarboxylic acid
C
$3-$hydroxy$-5-$cyanocyclohex$-2-$enoic acid
D
$5-$cyano$-3-$hydroxycyclohex$-2-$enecarboxylic acid

Solution

(D) $1$. Identify the principal functional group: The carboxylic acid group $(-COOH)$ has the highest priority and is attached to the ring,so the parent name will end in $cyclohexanecarboxylic$ $acid$.
$2$. Number the ring: Start numbering from the carbon atom attached to the $-COOH$ group as $C-1$. To give the lowest possible locants to the double bond,hydroxyl group,and cyano group,we number the ring in a counter-clockwise direction.
$3$. Assign locants: The double bond starts at $C-2$,the hydroxyl group $(-OH)$ is at $C-3$,and the cyano group $(-CN)$ is at $C-5$.
$4$. Assemble the name: The substituents are $5-$cyano and $3-$hydroxy. The double bond is at position $2$. Combining these,we get $5-$cyano$-3-$hydroxycyclohex$-2-$enecarboxylic acid.
461
MediumMCQ
Which of the following has an incorrect $IUPAC$ name?
A
$2-$phenylacetic acid
B
$NH_2-CH_2-CH=CH_2$: $\text{prop}-2-\text{en}-1-\text{amine}$
C
$3-$methylcyclohexanecarbaldehyde
D
$(CH_3)_2C=CHCOCH_3$: $4-\text{methylpent}-3-\text{en}-2-\text{one}$

Solution

(C) Let us evaluate the given names:
$A$: The structure is $C_6H_5-CH_2-COOH$. The $IUPAC$ name is $2-$phenylacetic acid or $2-$phenylethanoic acid. This is correct.
$B$: The structure is $NH_2-CH_2-CH=CH_2$. The numbering starts from the carbon attached to the amine group. The name is $\text{prop}-2-\text{en}-1-\text{amine}$. This is correct.
$C$: The structure is a cyclohexane ring with a $-CHO$ group and a $-CH_3$ group at the $3-$position. When the $-CHO$ group is attached to a ring,the suffix used is $\text{carbaldehyde}$. Thus,the name is $3-$methylcyclohexanecarbaldehyde. The name '$3-$methylcyclohexanal' is incorrect.
$D$: The structure is $(CH_3)_2C=CHCOCH_3$. Numbering from the ketone end gives $4-\text{methylpent}-3-\text{en}-2-\text{one}$. This is correct.
Therefore,option $C$ has the incorrect $IUPAC$ name.
462
DifficultMCQ
Which of the following is correctly matched?
Common name $\to$ $IUPAC$ name
A
Acetanilide $\to$ $2-$aminotoluene
B
Phenetole $\to$ $2-$methoxypropane
C
Phthaldehyde $\to$ benzene$-1, 2-$dicarbaldehyde
D
Acrolein $\to$ pentanal

Solution

(C) The correct match is Phthaldehyde $\to$ benzene$-1, 2-$dicarbaldehyde.
$1.$ Acetanilide is $N-$phenylethanamide.
$2.$ Phenetole is ethoxybenzene.
$3.$ Acrolein is prop$-2-$enal.
$4.$ Phthaldehyde (or phthalaldehyde) is benzene$-1, 2-$dicarbaldehyde.
463
DifficultMCQ
The $IUPAC$ name of the given compound is:
Question diagram
A
$6-$Oxo$-4-$formylcyclohexanecarboxylic acid
B
$4-$Formyl$-2-$oxocyclohexanecarboxylic acid
C
$4-$Formyl$-2-$oxocyclohexanoic acid
D
$1-$Carboxy$-4-$formyl$-2-$oxocyclohexane

Solution

(B) $1$. Identify the principal functional group: The carboxylic acid group $(-COOH)$ has the highest priority and is attached to the ring,so the parent name is cyclohexanecarboxylic acid.
$2$. Number the ring: Start numbering from the carbon attached to the $-COOH$ group as $C-1$.
$3$. Assign positions to other substituents: The ketone group $(=O)$ is at position $2$ and the formyl group $(-CHO)$ is at position $4$.
$4$. Combine the names: The substituents are $4-$formyl and $2-$oxo. Arranging them alphabetically,we get $4-$formyl$-2-$oxocyclohexanecarboxylic acid.
464
MediumMCQ
The $IUPAC$ name of the following compound is
Question diagram
A
$1-$Ethyl cyclohex$-1-$en$-3-$ol
B
$1-$Ethyl$-3-$hydroxy cyclohex$-1-$ene
C
$3-$Ethyl cyclohex$-2-$en$-1-$ol
D
$2-$Ethyl$-6-$hydroxy cyclohexene

Solution

(C) $1$. Identify the principal functional group: The hydroxyl group $(-OH)$ has higher priority than the double bond. Therefore,the suffix is $-ol$ and the carbon attached to $-OH$ is assigned position $1$.
$2$. Number the ring: Start numbering from the carbon attached to the $-OH$ group $(C-1)$. Proceed in the direction that gives the double bond the lowest possible locant. Moving towards the double bond,the double bond starts at $C-2$. Thus,the ring is a cyclohex$-2-$ene derivative.
$3$. Identify substituents: There is an ethyl group $(-CH_2CH_3)$ attached at position $3$.
$4$. Combine: The name is $3-$ethylcyclohex$-2-$en$-1-$ol.
465
MediumMCQ
What is the number of carbon atoms in the principal carbon chain of the given structure?
Question diagram
A
$7$
B
$4$
C
$6$
D
$5$

Solution

(A) The given structure is a diene. According to $IUPAC$ nomenclature rules,the principal carbon chain must include the maximum number of multiple bonds (double bonds in this case).
Counting the carbon atoms in the longest chain containing both double bonds:
Starting from the left end,the chain consists of $7$ carbon atoms in a continuous sequence.
Therefore,the number of carbon atoms in the principal carbon chain is $7$.
466
EasyMCQ
What is the $IUPAC$ name of crotonic acid?
A
$But-3-enoic$ acid
B
$But-2-enoic$ acid
C
$Propenoic$ acid
D
$3-Methylbut-2-enoic$ acid

Solution

(B) The chemical formula for crotonic acid is $CH_3-CH=CH-COOH$.
In the $IUPAC$ nomenclature,the longest carbon chain containing the carboxylic acid group is selected.
The chain has $4$ carbon atoms,so the parent alkane is butane.
The double bond starts at the $C-2$ position.
Therefore,the $IUPAC$ name is $But-2-enoic$ acid.
467
DifficultMCQ
Which $IUPAC$ name is incorrectly matched?
A
$CH_3-C(CH_3)_2-CH_2-CH_3 \to 2,2-\text{dimethylbutane}$
B
$CH_3-CH(OH)-CH=CH_2 \to \text{But-3-en-2-ol}$
C
$CH_3-CH=CH-C \equiv CH \to \text{Pent-2-en-4-yne}$
D
$CH_3-C(CH_3)_2-CH_2-NH_2 \to 2,2-\text{dimethylpropan-1-amine}$

Solution

(C) The correct $IUPAC$ name for $CH_3-CH=CH-C \equiv CH$ is $Pent-3-en-1-yne$.
According to $IUPAC$ rules,when both double and triple bonds are present,numbering starts from the end that gives the lower locant to the multiple bonds.
If the locants are the same from both ends,the double bond is given priority for the lower number.
In this case,numbering from the right gives the double bond position $3$ and the triple bond position $1$ ($1,3$-combination),whereas numbering from the left gives $2$ and $4$ ($2,4$-combination).
Therefore,$Pent-3-en-1-yne$ is the correct name,making option $C$ the incorrectly matched one.
468
MediumMCQ
Which of the following does not have an asymmetric carbon?
A
$1-$chloro$-2-$bromocyclopropane
B
$2-$methylazetidine
C
$C_2H_2ClBr$
D
$3-$chlorobutane

Solution

(C) An asymmetric carbon (chiral center) is a carbon atom bonded to four different groups.
$A$. In $1$-chloro-$2$-bromocyclopropane,the carbons at positions $1$ and $2$ are bonded to four different groups (e.g.,$C_1$ is bonded to $H$,$Cl$,$C_2$,and $C_3$),so it has asymmetric carbons.
$B$. In $2$-methylazetidine,the carbon at position $2$ is bonded to $H$,$CH_3$,$N$,and $C_3$,making it an asymmetric carbon.
$C$. In $C_2H_2ClBr$ (which is $CH_2Cl-CH_2Br$ or $CHCl=CHBr$),there is no carbon atom bonded to four different groups. For example,in $1$-bromo-$2$-chloroethane $(CH_2Cl-CH_2Br)$,each carbon is bonded to two $H$ atoms,which are identical.
$D$. In $3$-chlorobutane $(CH_3-CH_2-CHCl-CH_3)$,the carbon at position $3$ is bonded to $H$,$Cl$,$CH_3$,and $CH_2CH_3$,which are four different groups,so it is an asymmetric carbon.
Therefore,the molecule that does not have an asymmetric carbon is $C_2H_2ClBr$.
469
MediumMCQ
$IUPAC$ name of the following compound is
$CH_3-CH=CH-CH_2-C\equiv CH$
A
Hex$-2-$en$-5-$yne
B
Hex$-5-$yn$-2-$ene
C
Hex$-4-$en$-1-$yne
D
Hex$-1-$yn$-4-$ene

Solution

(C) $1$. Identify the longest carbon chain containing both the double bond and the triple bond. The chain has $6$ carbon atoms,so the parent alkane is hexane.
$2$. Number the chain from the end that gives the lower locant to the multiple bonds. Numbering from the left gives the double bond at $C-2$ and the triple bond at $C-5$. Numbering from the right gives the triple bond at $C-1$ and the double bond at $C-4$.
$3$. According to $IUPAC$ rules,if both double and triple bonds are present,the double bond is given priority for the lower number if there is a choice. However,the rule states we choose the set of locants that is lower. Comparing $(2, 5)$ and $(1, 4)$,the set $(1, 4)$ is lower.
$4$. Therefore,the correct numbering starts from the right: $C-1$ is the triple bond,$C-4$ is the double bond.
$5$. The name is constructed as $Hex-4-en-1-yne$.
470
DifficultMCQ
The $IUPAC$ name of the following compound is:
Question diagram
A
$N$-cyclohexylbenzamide
B
$N$-phenyl-$N$-cyclohexylmethanamide
C
$N$-phenylcyclohexanecarboxamide
D
$N$-cyclohexyl-$N$-phenylmethylamide

Solution

(C) The given compound is an amide.
The parent chain is the cyclohexane ring attached to the carbonyl carbon,which is named as cyclohexanecarboxamide.
$A$ phenyl group $(-C_6H_5)$ is attached to the nitrogen atom of the amide group.
Therefore,the $IUPAC$ name is $N$-phenylcyclohexanecarboxamide.
471
EasyMCQ
The number of electrons in $-CHO$ is ...............
A
$15$
B
$14$
C
$16$
D
$17$

Solution

(A) The $-CHO$ group consists of one Carbon atom,one Hydrogen atom,and one Oxygen atom.
Atomic number of Carbon $(C)$ = $6$ (Number of electrons = $6$)
Atomic number of Hydrogen $(H)$ = $1$ (Number of electrons = $1$)
Atomic number of Oxygen $(O)$ = $8$ (Number of electrons = $8$)
Total number of electrons = $6 + 1 + 8 = 15$.
472
MediumMCQ
The $IUPAC$ name of the structure is:
Question diagram
A
$N$-Cyclohexylbenzamide
B
$N$-Phenyl-$N$-cyclohexylmethanamide
C
$N$-Phenylcyclohexanecarboxamide
D
$N$-Cyclohexyl-$N$-phenylmethylamide

Solution

(C) The given structure is a secondary amide where a phenyl group $(-C_6H_5)$ is attached to the nitrogen atom and a cyclohexane ring is attached to the carbonyl carbon.
According to $IUPAC$ nomenclature for amides,the parent chain is the one containing the carbonyl group. Here,it is a cyclohexane ring attached to a carboxamide group,making it a cyclohexane carboxamide.
The substituent on the nitrogen atom is a phenyl group,denoted as $N$-phenyl.
Combining these,the $IUPAC$ name is $N$-phenylcyclohexanecarboxamide.
473
MediumMCQ
The $IUPAC$ name of the given compound $CH_3-CH=CH-COOC_2H_5$ is
A
Ethyl $1-$butenoate
B
Ethyl $2-$butenoate
C
Ethyl propenoate
D
Propene ethyl methanoate

Solution

(B) The given compound is $CH_3-CH=CH-COOC_2H_5$.
It is an ester.
The alkyl group attached to the oxygen atom is an ethyl group $(C_2H_5)$.
The parent acid chain contains $4$ carbon atoms,and the double bond starts at the $2^{nd}$ carbon position.
Therefore,the $IUPAC$ name is Ethyl $2-$butenoate.
474
MediumMCQ
The $IUPAC$ name of the given compound is:
Question diagram
A
$5-$Bromo$-3-$chlorohex$-1-$ene
B
$2-$Bromo$-4-$chlorohex$-5-$ene
C
$3-$Chloro$-5-$bromohexene
D
$4-$Chloro$-2-$bromohex$-6-$ene

Solution

(A) $1$. Identify the longest carbon chain containing the double bond. The chain has $6$ carbon atoms,so the parent alkane is hexane,and with the double bond at position $1$,it is hex$-1-$ene.
$2$. Number the chain starting from the end that gives the double bond the lowest possible locant. Thus,the double bond starts at $C-1$.
$3$. Identify the substituents: a bromo group $(-Br)$ is at $C-5$ and a chloro group $(-Cl)$ is at $C-3$.
$4$. Arrange the substituents in alphabetical order: Bromo comes before Chloro.
$5$. Combining these,the name is $5-$Bromo$-3-$chlorohex$-1-$ene.
475
DifficultMCQ
The $IUPAC$ name of the given compound is:
Question diagram
A
Ethane dioic anhydride
B
Butane dioic anhydride
C
Butanoic anhydride
D
Ethanoic anhydride

Solution

(B) The given structure is a cyclic anhydride formed from succinic acid $(butanedioic \ acid)$.
In the structure,there are four carbon atoms in the main chain (including the two carbonyl carbons).
The parent dicarboxylic acid is $butanedioic \ acid$.
When it forms a cyclic anhydride,the name is derived by replacing 'acid' with 'anhydride'.
Thus,the $IUPAC$ name is $butanedioic \ anhydride$ (also commonly known as succinic anhydride).
476
MediumMCQ
The $IUPAC$ name of the given compound is $CH_3-CH(CN)-CH(CH=CH_2)-CH_2-CH_3$.
A
$2-$ Cyano $-3-$ vinylpentane
B
$2-$ Methyl $-3-$ vinylpentanenitrile
C
$3-$ Ethyl $-2-$ methylpent $-4-$ ene $-1-$ nitrile
D
$2-$ Methyl $-3-$ ethylpent $-4-$ ene $-1-$ nitrile

Solution

(C) $1$. The principal functional group is the nitrile group $(-CN)$,so it is assigned the lowest possible number,$C-1$.
$2$. The parent carbon chain must include the $-CN$ carbon and the double bond. The longest chain containing these is a $5$-carbon chain (pentene derivative).
$3$. Numbering: $C^1(N) - C^2H(CH_3) - C^3H(CH_2CH_3) - C^4H = C^5H_2$.
$4$. Substituents: $A$ methyl group at $C-2$ and an ethyl group at $C-3$.
$5$. Alphabetical order: Ethyl comes before Methyl.
$6$. The correct $IUPAC$ name is $3-$ Ethyl $-2-$ methylpent $-4-$ ene $-1-$ nitrile.
477
MediumMCQ
Which of the following is an incorrect match?
A
$3-$Bromobut$-1-$ene
Option A
B
$3-$Methoxyprop$-1-$ene
Option B
C
$2-$Methylpropan$-2-$ol
D
All of these

Solution

(D) All the given matches are incorrect according to $IUPAC$ nomenclature rules:
$(A)$ For the structure $CH_2=CH-CH(Br)-CH_3$,the correct $IUPAC$ name is $3-$bromobut$-1-$ene (the double bond has priority over the halogen).
$(B)$ For the structure $CH_2=CH-CH_2-OCH_3$,the correct $IUPAC$ name is $3-$methoxyprop$-1-$ene (the double bond has priority over the ether group).
$(C)$ For the structure $CH_3-C(CH_3)(OH)-CH_3$,the correct $IUPAC$ name is $2-$methylpropan$-2-$ol.
478
MediumMCQ
The $IUPAC$ name of the compound $CH_2 = CH - CH(CH_3) - CH_3$ is
A
$1,1-dimethyl-2-propene$
B
$2-vinyl propene$
C
$3-methylbut-1-ene$
D
$1-isopropyl ethene$

Solution

(C) The longest carbon chain containing the double bond has $4$ carbon atoms,making the parent chain 'butene'.
Numbering starts from the end closer to the double bond to give it the lowest possible number $(1)$.
$A$ methyl substituent is located at the $3^{rd}$ carbon.
Therefore,the $IUPAC$ name is $3-methylbut-1-ene$.
479
MediumMCQ
$IUPAC$ name of the following compound $NC-CH_2-CH(CN)-CH_2-CN$ is:
A
$3-$cyanopentane$-1,5-$dinitrile
B
Propane$-1,2,3-$tricarbonitrile
C
Propane$-1,2,3-$trinitrile
D
Propane-tricyanide

Solution

(B) The correct answer is $(B)$.
According to $IUPAC$ nomenclature rules,when three or more identical carbon-containing functional groups (like $-CN$) are attached to the same parent chain,the carbon atoms of these functional groups are excluded from the main chain.
In the compound $NC-CH_2-CH(CN)-CH_2-CN$,the main chain consists of $3$ carbon atoms (propane).
The suffix used for the $-CN$ group in this specific situation is 'carbonitrile'.
Therefore,the correct name is Propane$-1,2,3-$tricarbonitrile.
480
DifficultMCQ
The $IUPAC$ name of the following compound is:
Question diagram
A
$3,4-$Dimethyl octa$-1,3,6-$triene
B
$3,7-$Dimethyl octa$-1,3,6-$triene
C
$2,6-$Dimethyl octa$-2,5,7-$triene
D
$2,6-$Dimethyl octa$-1,5,7-$triene

Solution

(B) $1$. Identify the longest carbon chain containing the maximum number of double bonds. The chain has $8$ carbon atoms (octa-).
$2$. Number the chain from the end that gives the lowest locants to the double bonds. Numbering from the right gives double bonds at positions $1, 3,$ and $6$.
$3$. The substituents are two methyl groups at positions $3$ and $7$.
$4$. Combining these,the name is $3,7-$Dimethyl octa$-1,3,6-$triene.
481
DifficultMCQ
Which of the following molecules does not contain a chiral carbon?
A
$2, 2-$ Dimethyl $-1, 3-$ dibromo hexane
B
Neopentyl chloride
C
$2-$ Chloro butane
D
$2-$ Pentanol

Solution

(B) chiral carbon is a carbon atom bonded to four different groups.
$1$. $2, 2-$ Dimethyl $-1, 3-$ dibromo hexane: The carbon at position $3$ is bonded to $-H, -Br, -CH_2-C(CH_3)_2-CH_3$ and $-CH_2-CH_2-CH_3$. Since all four groups are different,it is chiral.
$2$. Neopentyl chloride $(CH_3-C(CH_3)_2-CH_2-Cl)$: The central carbon is bonded to two identical $-CH_3$ groups,and the terminal carbon is bonded to two identical $-H$ atoms. No carbon is bonded to four different groups. Thus,it is achiral.
$3$. $2-$ Chloro butane $(CH_3-CHCl-CH_2-CH_3)$: The carbon at position $2$ is bonded to $-H, -Cl, -CH_3$ and $-CH_2-CH_3$. It is chiral.
$4$. $2-$ Pentanol $(CH_3-CH(OH)-CH_2-CH_2-CH_3)$: The carbon at position $2$ is bonded to $-H, -OH, -CH_3$ and $-CH_2-CH_2-CH_3$. It is chiral.
Therefore,Neopentyl chloride does not contain a chiral carbon.
482
MediumMCQ
Which of the following is an incorrect $IUPAC$ name?
A
$CH_3-CH(OH)-CH_2-CH_3$ : $2-$Butanol
B
$CH_3-CH_2-Cl$ : Chloroethane
C
$(C_2H_5)_2NH$ : Diethylamine
D
All of the above are incorrect $IUPAC$ names

Solution

(D) The question asks for the incorrect $IUPAC$ name.
$1$. For $CH_3-CH(OH)-CH_2-CH_3$,the $IUPAC$ name is $2-$Butanol,not $2-$Hydroxybutane.
$2$. For $CH_3-CH_2-Cl$,the $IUPAC$ name is Chloroethane,not Ethyl chloride (which is a common name).
$3$. For $(C_2H_5)_2NH$,the $IUPAC$ name is $N-$Ethylethanamine,not Diethylamine (which is a common name).
Since all options provided are either common names or incorrect $IUPAC$ nomenclature,all are incorrect as $IUPAC$ names.
483
MediumMCQ
The $IUPAC$ name of the compound $CH_3-C(=O)-CH_2-C(CH_3)_2-CN$ is:
A
$4-$Cyano$-4-$methyl$-2-$oxopentane
B
$2-$Cyano$-2-$methyl$-4-$oxopentane
C
$2,2-$Dimethyl$-4-$oxopentanenitrile
D
$4-$Cyano$-4-$methyl$-2-$pentanone

Solution

(C) The functional groups present are nitrile $(-CN)$ and ketone $( > C=O)$.
According to $IUPAC$ priority rules,the nitrile group has higher priority than the ketone group.
The principal functional group is nitrile,and the ketone is treated as a substituent (oxo).
Numbering starts from the nitrile carbon as $C1$.
The parent chain has $5$ carbons (pentanenitrile).
There are two methyl groups at $C2$ and an oxo group at $C4$.
Thus,the name is $2,2-$dimethyl$-4-$oxopentanenitrile.
484
EasyMCQ
The correct structure of $4-bromo-3-methylbut-1-ene$ is
A
$Br-CH=C(CH_3)_2$
B
$CH_2=CH-CH(CH_3)-CH_2Br$
C
$CH_2=C(CH_3)-CH_2-CH_2Br$
D
$CH_3-C(CH_3)=CH-CH_2Br$

Solution

(B) The $IUPAC$ name $4-bromo-3-methylbut-1-ene$ indicates a $4$-carbon chain $(but)$ with a double bond at position $1$ $(but-1-ene)$.
At position $3$,there is a methyl group $(-CH_3)$,and at position $4$,there is a bromine atom $(-Br)$.
Constructing the chain: $C1(H_2)=C2(H)-C3(H)(CH_3)-C4(H_2)Br$.
Thus,the correct structure is $CH_2=CH-CH(CH_3)-CH_2Br$.
485
EasyMCQ
The correct $IUPAC$ name for the given structure is:
Question diagram
A
$5-$methyl$-4-(1',2'-$dimethylpropyl)heptane
B
$3-$methyl$-4-(1',2'-$dimethylpropyl)heptane
C
$2,3,5-$trimethyl$-4-$propylheptane
D
$4-$propyl$-2,3,5-$trimethylheptane

Solution

(C) $1$. Identify the longest carbon chain. The longest chain in the given structure contains $7$ carbon atoms (heptane).
$2$. Number the chain from the end that gives the lowest locants to the substituents. Numbering from right to left gives the substituents at positions $2, 3, 4,$ and $5$.
$3$. The substituents are three methyl groups at positions $2, 3,$ and $5$,and a propyl group at position $4$.
$4$. Combining these,the correct $IUPAC$ name is $2,3,5-$trimethyl$-4-$propylheptane.
486
MediumMCQ
The incorrect $IUPAC$ name is
A
$CH_3-C(=O)-CH(CH_3)-CH_3$ $2-$methyl$-3-$butanone
B
$CH_3-CH(CH_3)-CH(CH_2CH_3)-CH_3$ $2,3-$dimethylpentane
C
$CH_3-C \equiv C-CH(CH_3)_2$ $4-$methyl$-2-$pentyne
D
$CH_3-CH(Cl)-CH(Br)-CH_3$ $3-$chloro$-2-$bromobutane

Solution

(A) In the structure $CH_3-C(=O)-CH(CH_3)-CH_3$,the principal functional group (ketone) should get the lowest possible number.
Numbering from the left,the ketone is at $C2$ and the methyl group is at $C3$.
Thus,the correct $IUPAC$ name is $3-$methyl$-2-$butanone.
$(d)$ In $CH_3-CH(Cl)-CH(Br)-CH_3$,the alphabetical order should be followed for substituents.
$B$ (bromo) comes before $C$ (chloro).
Thus,the correct $IUPAC$ name is $2-$bromo$-3-$chlorobutane.
487
EasyMCQ
The $IUPAC$ name of the compound given below is:
Question diagram
A
$3-$methyl$-4-$ethyloctane
B
$2, 3-$diethylheptane
C
$5-$ethyl$-6-$methyloctane
D
$4-$ethyl$-3-$methyloctane

Solution

(D) $1$. Identify the longest carbon chain. The longest chain in the given structure contains $8$ carbon atoms,so the parent alkane is octane.
$2$. Number the chain from the end that gives the lowest locants to the substituents.
$3$. Numbering from left to right gives substituents at positions $3$ and $4$. Numbering from right to left gives substituents at positions $5$ and $6$.
$4$. Following the lowest locant rule,we number from left to right.
$5$. At position $3$,there is a methyl group $(-CH_3)$,and at position $4$,there is an ethyl group $(-CH_2CH_3)$.
$6$. According to $IUPAC$ rules,substituents are listed in alphabetical order. Therefore,ethyl comes before methyl.
$7$. The correct name is $4-$ethyl$-3-$methyloctane.
488
EasyMCQ
The $IUPAC$ name of the following compound is $CH_3-CH(CH_3)-CH_2-CH=CH-CH=CH-CH(CH_3)-CH_2-CH_3$:
A
$1,1,7,7-$ tetramethyl $-2,5-$ octadiene
B
$2,8-$ dimethyl $-3,6-$ decadiene
C
$1,5-$ di-iso-propyl $-1,4-$ hexadiene
D
$2,8-$ dimethyl $-4,6-$ decadiene

Solution

(D) $1$. Identify the longest carbon chain containing both double bonds,which consists of $10$ carbon atoms (decadiene).
$2$. Number the chain from the end that gives the lowest locants to the double bonds and substituents.
$3$. Numbering from left to right: $CH_3(1)-CH(CH_3)(2)-CH_2(3)-CH(4)=CH(5)-CH(6)=CH(7)-CH(CH_3)(8)-CH_2(9)-CH_3(10)$.
$4$. The double bonds are at positions $4$ and $6$,and methyl groups are at positions $2$ and $8$.
$5$. Therefore,the $IUPAC$ name is $2,8-$ dimethyl $-4,6-$ decadiene.
489
Medium
Expand each of the following condensed formulas into their complete structural formulas.
$(a)$ $CH_3-CH_2-CO-CH_2-CH_3$
$(b)$ $CH_3-CH=CH-CH_2-CH_2-CH_2-CH_3$

Solution

(N/A) The condensed formula $CH_3-CH_2-CO-CH_2-CH_3$ represents pentan-$3$-one. Its complete structural formula is:
$H-C(H)(H)-C(H)(H)-C(=O)-C(H)(H)-C(H)(H)-H$
$(b)$ The condensed formula $CH_3-CH=CH-CH_2-CH_2-CH_2-CH_3$ represents hept-$2$-ene. Its complete structural formula is:
$H-C(H)(H)-C(H)=C(H)-C(H)(H)-C(H)(H)-C(H)(H)-C(H)(H)-H$
490
Medium
For each of the following compounds,write a condensed formula and also their bond-line formula.
$(a)$ $HOCH_{2}CH_{2}CH_{2}CH(CH_{3})CH(CH_{3})CH_{3}$
$(b)$ $N \equiv C-CH(OH)-C \equiv N$

Solution

(N/A) Condensed formula:
$(a)$ $HO(CH_{2})_{3}CH(CH_{3})CH(CH_{3})_{2}$
$(b)$ $HOCH(CN)_{2}$
Bond-line formula:
$(a)$ $A$ chain of $6$ carbons with an $-OH$ group at the first carbon,a methyl group at the $4^{th}$ carbon,and a methyl group at the $5^{th}$ carbon.
$(b)$ $A$ central carbon atom bonded to an $-OH$ group and two $-CN$ groups.
491
MediumMCQ
Expand each of the following bond-line formulas to show all the atoms including carbon and hydrogen:
Question diagram
A
$(a)$ Cyclohexyl group attached to an isopropyl group.
B
$(b)$ Octane chain.
C
$(c)$ But$-3-$yn$-2-$ol.
D
$(d)$ $2,3-$Dimethylbutane.

Solution

(N/A) To expand bond-line formulas,replace each vertex and terminal point with a carbon atom and add the appropriate number of hydrogen atoms to satisfy the tetravalency of carbon.
$(a)$ The structure is isopropylcyclohexane. The expanded form shows a cyclohexane ring with an isopropyl group attached at one position.
$(b)$ The structure is octane $(CH_3-CH_2-CH_2-CH_2-CH_2-CH_2-CH_2-CH_3)$.
$(c)$ The structure is but$-3-$yn$-2-$ol $(HC \equiv C-CH_2-CH(OH)-CH_3)$.
$(d)$ The structure is $2,3-$dimethylbutane $((CH_3)_2CH-CH(CH_3)_2)$.
492
Medium
Structures and $IUPAC$ names of some hydrocarbons are given below. Explain why the names given in the parentheses are incorrect.
$(a)$ $CH_3-CH(CH_3)-CH_2-CH_2-CH(CH_3)-CH(CH_3)-CH_2-CH_3$
Name: $2,5,6-$Trimethyloctane [and not $3,4,7-$Trimethyloctane]
$(b)$ $CH_3-CH_2-CH(CH_2CH_3)-CH_2-CH(CH_3)-CH_2-CH_3$
Name: $3-$Ethyl$-5-$methylheptane [and not $5-$Ethyl$-3-$methylheptane]

Solution

(A) According to the lowest locant rule,the set of locants $2,5,6$ is lower than $3,4,7$. Therefore,$2,5,6-$trimethyloctane is the correct name.
$(b)$ When substituents are at equivalent positions from either end of the chain,the lower number is assigned to the substituent that comes first in the alphabetical order. Since $E$ (Ethyl) comes before $M$ (Methyl),the name $3-$ethyl$-5-$methylheptane is correct.
493
DifficultMCQ
Write the $IUPAC$ names of the following compounds:
A
$(i) CH_3-CH_2-CH(OH)-CH_2-CH_2-CH(CH_3)-CH_2-CH_3$
B
$(ii) CH_3-CH_2-CO-CH_2-CO-CH_3$
C
$(iii) CH_3-CO-CH_2-CH_2-CH_2-COOH$
D
$(iv) HC \equiv C-CH=CH-CH=CH_2$

Solution

(N/A) $(i)$ The functional group present is an alcohol $(-OH)$. The longest chain containing $-OH$ has $8$ carbon atoms. The $-OH$ is on carbon atom $3$ and a methyl group is at carbon $6$. The name is $6-$Methyloctan$-3-$ol.
$(ii)$ The functional group is ketone $(>C=O)$. Two keto groups are at carbons $2$ and $4$. The longest chain has $6$ carbon atoms. The name is Hexane$-2,4-$dione.
$(iii)$ The principal functional group is carboxylic acid $(-COOH)$. The keto group is at carbon $5$. The longest chain has $6$ carbon atoms. The name is $5-$Oxohexanoic acid.
$(iv)$ Two $C=C$ double bonds are at carbons $1$ and $3$,and one $C \equiv C$ triple bond is at carbon $5$. The longest chain has $6$ carbon atoms. The name is Hexa$-1,3-$dien$-5-$yne.
494
Difficult
Derive the structure of $(i)$ $2-$Chlorohexane,$(ii)$ Pent$-4-$en$-2-$ol,$(iii)$ $3-$Nitrocyclohexene,$(iv)$ Cyclohex$-2-$en$-1-$ol,$(v)$ $6-$Hydroxyheptanal.

Solution

(N/A) $(i)$ 'hexane' indicates the presence of $6$ carbon atoms in the chain. The functional group chloro is present at carbon $2$. Hence,the structure is $CH_3-CH_2-CH_2-CH_2-CH(Cl)-CH_3$.
$(ii)$ 'pent' indicates that the parent hydrocarbon contains $5$ carbon atoms. 'en' and 'ol' correspond to the functional groups $C=C$ and $-OH$ at carbon atoms $4$ and $2$ respectively. Thus,the structure is $CH_2=CH-CH_2-CH(OH)-CH_3$.
$(iii)$ $A$ six-membered ring containing a carbon-carbon double bond is implied by cyclohexene. The prefix $3-$nitro means that a nitro group is present on $C-3$. The double bond gets preference over the $-NO_2$ group. The structure is a cyclohexene ring with a double bond between $C-1$ and $C-2$ and a $-NO_2$ group at $C-3$.
$(iv)$ '$1-$ol' means that a $-OH$ group is present at $C-1$. The $-OH$ group is the principal functional group and gets preference over the $C=C$ bond. Thus,the structure is a cyclohexene ring with $-OH$ at $C-1$ and the double bond between $C-2$ and $C-3$.
$(v)$ 'heptanal' indicates an aldehyde containing $7$ carbon atoms. The '$6-$hydroxy' indicates that an $-OH$ group is present at carbon $6$. Thus,the structural formula is $CH_3-CH(OH)-CH_2-CH_2-CH_2-CH_2-CHO$.
495
Medium
Write the structural formula of:
$(a)$ $o-$Ethylanisole,
$(b)$ $p-$Nitroaniline,
$(c)$ $2,3-$Dibromo$-1-$phenylpentane,
$(d)$ $4-$Ethyl$-1-$fluoro$-2-$nitrobenzene.

Solution

(N/A) $o-$Ethylanisole: $A$ benzene ring with a methoxy group $(-OCH_3)$ at position $1$ and an ethyl group $(-C_2H_5)$ at position $2$.
$(b)$ $p-$Nitroaniline: $A$ benzene ring with an amino group $(-NH_2)$ at position $1$ and a nitro group $(-NO_2)$ at position $4$.
$(c)$ $2,3-$Dibromo$-1-$phenylpentane: $A$ pentane chain with a phenyl group $(-C_6H_5)$ at position $1$ and bromine atoms at positions $2$ and $3$. The structure is $C_6H_5-CH_2-CH(Br)-CH(Br)-CH_2-CH_3$.
$(d)$ $4-$Ethyl$-1-$fluoro$-2-$nitrobenzene: $A$ benzene ring with a fluorine atom at position $1$,a nitro group at position $2$,and an ethyl group at position $4$.
496
Medium
Write bond line formulas for: Isopropyl alcohol,$2,3-$Dimethylbutanal,Heptan$-4-$one.

Solution

(N/A) The bond line formulas for the given compounds are as follows:
$(a)$ Isopropyl alcohol: $A$ $V$-shaped chain with an $-OH$ group attached to the central carbon.
$(b)$ $2,3-$Dimethylbutanal: $A$ four-carbon chain with an aldehyde group $(-CHO)$ at position $1$ and methyl groups at positions $2$ and $3$.
$(c)$ Heptan$-4-$one: $A$ seven-carbon chain with a ketone group $(C=O)$ at position $4$.
497
Medium
Give the $IUPAC$ names of the following compounds:
Question diagram

Solution

(N/A) $1-phenylpropane$ (Note: The provided solution image incorrectly labels it as $3-phenylpropane$)
$(b)$ $3-methylpentanenitrile$ (Note: The provided solution image incorrectly labels it as $2-methyl-1-cyanobutane$)
$(c)$ $2,5-dimethylheptane$
$(d)$ $3-bromo-3-chloroheptane$
$(e)$ $3-chloropropanal$
$(f)$ $2,2-dichloroethanol$ (Note: The provided solution image incorrectly labels it as $1,1-dichloro-2-ethanol$)
498
MediumMCQ
Which of the following represents the correct $IUPAC$ name for the compounds concerned?
$(a)$ $2,2-$ Dimethylpentane or $2-$ Dimethylpentane
$(b)$ $2,4,7-$ Trimethyloctane or $2,5,7-$ Trimethyloctane
$(c)$ $2-$ Chloro$-4-$methylpentane or $4-$ Chloro$-2-$methylpentane
$(d)$ But$-3-$yn$-1-$ol or But$-4-$ol$-1-$yne
A
$2,2-$ Dimethylpentane
B
$2,4,7-$ Trimethyloctane
C
$2-$ Chloro$-4-$methylpentane
D
But$-3-$yn$-1-$ol

Solution

(A, B, C, D) The $IUPAC$ nomenclature rules dictate the following:
$(a)$ The prefix $di-$ indicates two identical substituents. Since two methyl groups are at $C-2$,the correct name is $2,2-$ dimethylpentane.
$(b)$ According to the lowest locant rule,the set $2,4,7$ is preferred over $2,5,7$. Thus,the correct name is $2,4,7-$ trimethyloctane.
$(c)$ When substituents are at equivalent positions,alphabetical priority determines the numbering. $Chloro$ comes before $methyl$,so $2-$ chloro$-4-$methylpentane is correct.
$(d)$ The alcohol group $(-OH)$ has higher priority than the alkyne group $(-C \equiv C-)$. The chain is numbered to give the principal functional group the lowest possible number. Thus,the correct name is But$-3-$yn$-1-$ol.

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