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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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301
MediumMCQ
Which among the following is the correct $IUPAC$ name of isoamylene?
A
$1-$Pentene
B
$2-$Methyl$-2-$butene
C
$3-$Methyl$-1-$butene
D
$2-$Methyl$-1-$butene

Solution

(B) Isoamylene is a common name for $2-$methyl$-2-$butene.
Its structure is $CH_3-C(CH_3)=CH-CH_3$.
According to $IUPAC$ nomenclature rules,the longest carbon chain containing the double bond is selected,which has $5$ carbons (pentene).
The double bond is at the $2$nd position,and a methyl group is at the $2$nd position.
Therefore,the correct $IUPAC$ name is $2-$methyl$-2-$butene.
302
DifficultMCQ
The $IUPAC$ name of the given compound is:
Question diagram
A
$3-$Methylcyclobut$-2-$en$-1-$ol
B
$4-$Methylcyclobut$-2-$en$-1-$ol
C
$4-$Methylcyclobut$-1-$en$-3-$ol
D
$2-$Methylcyclobut$-3-$en$-1-$ol

Solution

(B) $1$. Identify the principal functional group: The $-OH$ group has the highest priority,so the parent chain is a cyclobutene derivative named as cyclobut$-2-$en$-1-$ol.
$2$. Numbering the ring: The carbon attached to the $-OH$ group is assigned position $1$. The numbering should proceed towards the double bond to give it the lowest possible locant.
$3$. Assigning locants: If we number clockwise starting from the $-OH$ carbon,the double bond starts at position $2$ and the methyl group is at position $4$. If we number counter-clockwise,the double bond starts at position $3$ and the methyl group is at position $2$. Following the lowest locant rule for the double bond,we choose the clockwise numbering.
$4$. Final Name: The substituent is a methyl group at position $4$. Thus,the correct $IUPAC$ name is $4-$methylcyclobut$-2-$en$-1-$ol.
303
MediumMCQ
The $IUPAC$ name of $C_6H_5CH=CHCOOH$ is:
A
cinnamic acid
B
$1-$phenyl$-2-$carboxyethane
C
$3-$phenylprop$-2-$enoic acid
D
dihydroxy$-3-$phenylpropionic acid

Solution

(C) The structure $C_6H_5CH=CHCOOH$ consists of a phenyl group attached to a three-carbon chain containing a carboxylic acid group and a double bond.
The longest carbon chain containing the carboxylic acid group has $3$ carbon atoms,making it a derivative of propanoic acid.
The double bond starts at the $2^{nd}$ carbon atom,so it is named prop$-2-$enoic acid.
$A$ phenyl group $(-C_6H_5)$ is attached to the $3^{rd}$ carbon atom.
Combining these,the $IUPAC$ name is $3-$phenylprop$-2-$enoic acid.
Its common name is cinnamic acid.
304
MediumMCQ
The $IUPAC$ name of $CH_3-COO-CH_2-COOH$ is:
A
$1-$ acetoxy acetic acid
B
$2-$ acetoxy ethanoic acid
C
$2-$ ethanoyloxyacetic acid
D
$2-$ ethanoyloxyethanoic acid

Solution

(D) The given compound is $CH_3-COO-CH_2-COOH$.
The principal functional group is the carboxylic acid $(-COOH)$,which gets the $C-1$ position.
The parent chain is ethanoic acid ($C-1$ is the carboxyl carbon,$C-2$ is the methylene carbon).
The substituent at the $C-2$ position is the $CH_3-COO-$ group,which is named as ethanoyloxy.
Combining these,the $IUPAC$ name is $2-$ethanoyloxyethanoic acid.
305
MediumMCQ
The $IUPAC$ name of the given compound is:
Question diagram
A
$2-$methoxy$-4-$nitrobenzaldehyde
B
$4-$nitroanisaldehyde
C
$3-$methoxy$-4-$formylnitrobenzene
D
$2-$formyl$-4-$nitroanisole

Solution

(A) The principal functional group is the aldehyde group $(-CHO)$,so the parent chain is benzaldehyde.
Numbering starts from the carbon attached to the $-CHO$ group as $C-1$.
Proceeding to give the lowest possible locants to the substituents,the methoxy group $(-OCH_3)$ is at position $2$ and the nitro group $(-NO_2)$ is at position $4$.
Following alphabetical order for substituents,the name is $2-$methoxy$-4-$nitrobenzaldehyde.
306
MediumMCQ
The $IUPAC$ name of the given compound is:
Question diagram
A
$cis, cis-9, 12-$ octadecadienoic acid
B
$cis, trans-9, 12-$ octadecadienoic acid
C
$9, 10-$ octadecadienoic acid
D
$9, 14-$ octadecadienoic acid

Solution

(A) $1$. The structure is $CH_3(CH_2)_4-CH=CH-CH_2-CH=CH-(CH_2)_7COOH$.
$2$. The longest carbon chain contains $18$ carbon atoms,so the parent alkane is octadecane.
$3$. There are two double bonds at positions $9$ and $12$ (numbering from the $COOH$ group as $C-1$).
$4$. The configuration at both double bonds is $cis$ because the hydrogen atoms are on the same side of the double bond.
$5$. Therefore,the $IUPAC$ name is $cis, cis-9, 12-$ octadecadienoic acid.
307
MediumMCQ
The suffix of the principal group,the prefixes for the other groups and the name of the parent in the structure $HO-CH_2-CH(CH_3)-CH=C(Cl)-CH_2-C(=O)-C(=O)OH$ are:
A
-oic acid,chloro,hydroxy,oxo,methyl,$4$-heptene
B
-oic acid,chloro,hydroxy,methyl,oxo,$4$-heptene
C
-one,carboxy,chloro,methyl,hydroxy,$4$-heptene
D
-one,carboxy,chloro,methyl,hydroxy,$4$-heptene

Solution

(B) The principal functional group is $-COOH$ (suffix: $-oic \ acid$).
The other groups are $-OH$ (hydroxy),$-Cl$ (chloro),$-CH_3$ (methyl),and $=O$ (oxo).
Numbering starts from the $-COOH$ carbon.
The parent chain has $7$ carbons with a double bond at $C4$ ($4$-heptene).
Alphabetical order of prefixes: chloro,hydroxy,methyl,oxo.
308
DifficultMCQ
The $IUPAC$ name of the compound $CH_3OOC-CH(CH_2OH)-COOCH_3$ is:
A
$2-$hydroxymethyl methyl propanedioate
B
Methyl $2-$hydroxymethyl propanedioate
C
Dimethyl $2-$hydroxymethyl propanedioate
D
$2-$hydroxymethyl dimethyl propanedioate

Solution

(C) The given compound is $CH_3OOC-CH(CH_2OH)-COOCH_3$.
This is an ester derivative of propanedioic acid.
The parent chain is a $3-$carbon chain with two ester groups $(-COOCH_3)$ at positions $1$ and $3$.
There is a hydroxymethyl group $(-CH_2OH)$ attached at the $2^{nd}$ position.
Thus,the $IUPAC$ name is Dimethyl $2-$hydroxymethylpropanedioate.
309
MediumMCQ
The $IUPAC$ name of $OHC-CH_2-CH_2-CH(CH_2-CHO)-CH_2-CHO$ is:
A
$4,4-$di(formylmethyl)butanal
B
$2-$(formylmethyl)butane$-1,4-$dicarbaldehyde
C
hexane$-3-$acetal$-1,6-$dial
D
$3-$(formylmethyl)hexane$-1,6-$dial

Solution

(D) $1.$ Identify the longest carbon chain containing the maximum number of $-CHO$ groups. The longest chain contains $6$ carbon atoms,including two $-CHO$ groups at the ends.
$2.$ Number the chain starting from the end that gives the substituent the lowest locant. Numbering from the right gives the substituent at position $3$.
$3.$ The substituent $-CH_2-CHO$ is named as a "formylmethyl" group.
$4.$ Combining these,the $IUPAC$ name is $3-$(formylmethyl)hexane$-1,6-$dial.
310
MediumMCQ
The $IUPAC$ name of the given compound is:
Question diagram
A
$2-$chlorocarbonyl ethylbenzoate
B
$2-$carboxyethyl benzoyl chloride
C
ethyl $2-$(chlorocarbonyl) benzoate
D
ethyl $1-$(chlorocarbonyl) benzoate

Solution

(C) $1$. Identify the principal functional group: The ester group $(-COOC_2H_5)$ has higher priority than the acid chloride group $(-COCl)$.
$2$. The parent chain is the benzoate ester,and the $-COCl$ group is treated as a substituent named 'chlorocarbonyl'.
$3$. Numbering the benzene ring: The carbon attached to the ester group is position $1$. The $-COCl$ group is at position $2$.
$4$. Therefore,the $IUPAC$ name is ethyl $2-$(chlorocarbonyl) benzoate.
311
MediumMCQ
The correct systematic name of the compound $CH_3-O-CO-CH_2-COOH$ is:
A
$2-$ acetoxy ethanoic acid
B
$2-$ methoxycarbonyl ethanoic acid
C
$3-$ methoxyformyl ethanoic acid
D
$2-$ methoxyformyl acetic acid

Solution

(B) The given compound is $CH_3-O-CO-CH_2-COOH$.
The principal functional group is the carboxylic acid $(-COOH)$.
The parent chain consists of two carbon atoms,which is ethanoic acid.
The substituent at the $2^{nd}$ position is the methoxycarbonyl group $(-COOCH_3)$.
Therefore,the $IUPAC$ name is $2-$ methoxycarbonyl ethanoic acid.
312
MediumMCQ
The $IUPAC$ name of the given compound is:
Question diagram
A
$1-$cyclohexyl$-3-$methylpent$-1-$ene
B
$3-$methyl$-5-$cyclohexylpent$-1-$ene
C
$1-$cyclohexyl$-3-$ethylbut$-1-$ene
D
$1-$cyclohexyl$-3,4-$dimethylbut$-1-$ene

Solution

(A) $1$. Identify the longest carbon chain containing the double bond. The chain has $5$ carbon atoms,so the parent alkane is pentane,and with the double bond at position $1$,it is pent-$1$-ene.
$2$. Number the chain starting from the end closer to the double bond. The double bond starts at $C-1$.
$3$. Identify the substituents: $A$ cyclohexyl group is attached at $C-1$,and a methyl group is attached at $C-3$.
$4$. Combining these,the $IUPAC$ name is $1$-cyclohexyl-$3$-methylpent-$1$-ene.
313
DifficultMCQ
The correct $IUPAC$ name of the compound $CH_3-CH_2-C(CH_3)=CH-CH(C_2H_5)-CH(CH_3)-CH_2-CH_2-CH_3$ is:
A
$5-$ethyl$-3, 6-$dimethylnon$-3-$ene
B
$5-$ethyl$-4, 7-$dimethylnon$-3-$ene
C
$4-$methyl$-5, 7-$diethyloct$-2-$ene
D
$2,4-$ethyl$-5-$methyl oct$-2-$ene

Solution

(A) $1.$ Select the longest carbon chain containing the double bond. The longest chain has $9$ carbons,so the parent alkane is nonane,and the alkene is nonene.
$2.$ Number the chain starting from the left to give the double bond the lowest possible locant,which is $C3$.
$3.$ Identify the substituents: an ethyl group at $C5$ and methyl groups at $C3$ and $C6$.
$4.$ Arrange substituents alphabetically: $5-$ethyl comes before $3, 6-$dimethyl.
$5.$ Combining these,the correct $IUPAC$ name is $5-$ethyl$-3, 6-$dimethylnon$-3-$ene.
314
MediumMCQ
Which of the following groups is divalent?
A
Benzoyl
B
Benzyl
C
Benzal
D
$p-$Tolyl

Solution

(C) monovalent group is formed by removing one hydrogen atom from an alkane or arene,while a divalent group is formed by removing two hydrogen atoms from the same carbon atom.
$1$. Benzoyl group $(C_6H_5CO-)$ is monovalent.
$2$. Benzyl group $(C_6H_5CH_2-)$ is monovalent.
$3$. Benzal group $(C_6H_5CH=)$ is divalent,as it is derived by removing two hydrogen atoms from the methyl group of toluene $(C_6H_5CH_3)$.
$4$. $p-$Tolyl group $(CH_3-C_6H_4-)$ is monovalent.
315
MediumMCQ
Select the correct match of $IUPAC$ name with structure.
A
$CH_3-COOCH_3 \to$ Methyl methanoate
B
$NH_2-CONH_2 \to$ Diamino ketone
C
$CH_3-CH(C_2H_5)-CH_2-CH(CH_3)_2 \to 2-$ Ethyl $-4-$ methylpentane
D
$CH_2=CH-CH(C_2H_5)-CHO \to 2-$ Ethylbut $-3-$ enal

Solution

(D) In option $(d)$,the structure $CH_2=CH-CH(C_2H_5)-CHO$ is correctly named as $2-$ ethylbut $-3-$ enal.
$(a)$ $CH_3-COOCH_3$ is methyl ethanoate.
$(b)$ $NH_2-CONH_2$ is urea or diaminomethanone.
$(c)$ $CH_3-CH(C_2H_5)-CH_2-CH(CH_3)_2$ is $2,4-$ dimethylhexane.
316
DifficultMCQ
What is the correct $IUPAC$ name of the given compound?
Question diagram
A
$1-$Ethenyl$-2-$ethynylcyclopropanoic acid
B
$2-$Ethenyl$-3-$ethynylcyclopropane carboxylic acid
C
$2-$Ethynyl$-3-$ethenylcyclopropane carboxylic acid
D
$2-$Ethenyl$-3-$ethynylcyclopropane$-1-$oic acid

Solution

(B) $1$. The principal functional group is the carboxylic acid $(-COOH)$ attached to the cyclopropane ring. The carbon atom of the ring attached to the $-COOH$ group is assigned position $1$.
$2$. The substituents are an ethenyl group $(-CH=CH_2)$ and an ethynyl group $(-C\equiv CH)$.
$3$. Numbering the ring to give the lowest locants to the substituents: if we number clockwise or counter-clockwise,the substituents are at positions $2$ and $3$.
$4$. According to $IUPAC$ rules,substituents are listed in alphabetical order: 'ethenyl' comes before 'ethynyl'.
$5$. Therefore,the ethenyl group is at position $2$ and the ethynyl group is at position $3$.
$6$. The correct name is $2-$ethenyl$-3-$ethynylcyclopropane carboxylic acid.
317
MediumMCQ
The $IUPAC$ name of $CH_3-CH(CH_3)-C(=O)-C(=O)-NHBr$ is
A
$N-Bromo-2-oxo-3-methylbutanamide$
B
$N-Bromo-2-oxo-4-methylbutanamide$
C
$N-Bromo-1,2-dioxo-3-methylbutanamide$
D
$N-Bromo-1-oxo-2-methylpropane$

Solution

(A) $1.$ The principal functional group is the amide $(-CONHBr)$.
$2.$ The longest carbon chain containing the amide group has $4$ carbons,so the parent name is butanamide.
$3.$ Numbering starts from the amide carbon: $C1$ is the amide carbon,$C2$ has a keto group $(=O)$,and $C3$ has a methyl group $(-CH_3)$.
$4.$ The bromine atom is attached to the nitrogen,denoted as $N-bromo$.
$5.$ Therefore,the $IUPAC$ name is $N-Bromo-2-oxo-3-methylbutanamide$.
318
MediumMCQ
The $IUPAC$ name of the given compound is:
Question diagram
A
$5-$Methylheptan$-3-$ol
B
$3-$Methylhept$-3-$en$-5-$ol
C
$5-$Methylhept$-4-$en$-3-$ol
D
$5-$Methylhept$-3-$en$-4-$ol

Solution

(C) $1$. Identify the longest carbon chain containing the principal functional group $(-OH)$ and the double bond. 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 right to left gives the $-OH$ group at position $3$.
$3$. The double bond starts at carbon $4$ (between $C4$ and $C5$),so it is a hept$-4-$en$-3-$ol derivative.
$4$. There is a methyl group at position $5$.
$5$. Combining these,the name is $5-$methylhept$-4-$en$-3-$ol.
319
DifficultMCQ
Write the $IUPAC$ name of the following structure $(E)$:
Question diagram
A
$2-$Ethyl$-3-$ethoxycarbonylpropanoic acid
B
$2-$Ethyl$-2-$ethoxycarbonylethanoic acid
C
$2-$Methoxycarbonylbutanoic acid
D
$2-$Ethoxycarbonylbutanoic acid

Solution

(D) The given structure is $CH_3CH_2-CH(COOCH_2CH_3)-COOH$.
$1$. Identify the principal functional group: The carboxylic acid group $(-COOH)$ has higher priority than the ester group $(-COOR)$. Thus,the parent chain is a butanoic acid derivative.
$2$. Numbering the chain: The carbon of the $-COOH$ group is assigned position $1$. The carbon attached to the ester group is at position $2$.
$3$. Substituent identification: At position $2$,there is an ethoxycarbonyl group $(-COOCH_2CH_3)$.
$4$. Combining the parts: The parent chain is a $4$-carbon chain (butanoic acid). At position $2$,we have an ethoxycarbonyl substituent. Therefore,the name is $2-$ethoxycarbonylbutanoic acid.
320
MediumMCQ
What is the prefix of an ester group?
A
Oate
B
Haloformyl
C
Carbalkoxy
D
Formyl

Solution

(C) In the $IUPAC$ nomenclature of organic compounds,the ester functional group $(-COOR)$ is named as an 'oate' suffix when it is the principal functional group. However,when it is treated as a substituent or when the carbon of the ester group is not included in the parent chain,it is named using the prefix 'alkoxycarbonyl' or 'carbalkoxy'.
321
MediumMCQ
Arrange the following functional groups in order of priority according to the $IUPAC$ system: $-CHO, -COOH, -SO_3H, -CONH_2$.
A
$-COOH > -CHO > -SO_3H > -CONH_2$
B
$-COOH > -SO_3H > -CONH_2 > -CHO$
C
$-SO_3H > -COOH > -CONH_2 > -CHO$
D
$-COOH > -CONH_2 > -CHO > -SO_3H$

Solution

(B) According to the $IUPAC$ priority rules for functional groups,the decreasing order of priority is:
$1. -COOH$ (Carboxylic acid)
$2. -SO_3H$ (Sulphonic acid)
$3. -CONH_2$ (Amide)
$4. -CHO$ (Aldehyde)
Therefore,the correct order is $-COOH > -SO_3H > -CONH_2 > -CHO$.
Thus,option $B$ is correct.
322
DifficultMCQ
What is the correct $IUPAC$ name of the following radical?
$-CH_2-CH(OH)-CH_3$
A
$2-$Hydroxypropyl
B
$1-$Hydroxypropan$-2-$yl
C
$2-$Propanol
D
$2-$Methylethanol

Solution

(A) The given radical is $-CH_2-CH(OH)-CH_3$.
To name this radical,we identify the longest carbon chain attached to the main group.
The carbon atom attached to the main chain is assigned position $1$.
Thus,the chain is a propyl group ($3$ carbons).
At position $2$,there is a hydroxyl $(-OH)$ group.
Therefore,the correct $IUPAC$ name for this radical is $2-$hydroxypropyl.
323
MediumMCQ
Which of the following is $2$-carboxyethyl?
A
$-CH_2-COOH$
B
$-CH_2-CH_2-CHO$
C
$-CH_2-CHO$
D
$-CH_2-CH_2-COOH$

Solution

(D) The ethyl group is $-CH_2-CH_2-$.
When a carboxy group $(-COOH)$ is attached to the second carbon atom of the ethyl chain,it is named as $2$-carboxyethyl.
The structure is $-CH_2-CH_2-COOH$.
324
MediumMCQ
The correct $IUPAC$ name of the following compound is:
Question diagram
A
But-$3$-en-$2$-ol
B
Butan-$2$-ol
C
But-$2$-en-$2$-ol
D
But-$1$-en-$3$-ol

Solution

(A) The given structure is $CH_2=CH-CH(OH)-CH_3$.
$1$. Identify the longest carbon chain containing the principal functional group $(-OH)$ and the double bond. The chain has $4$ carbon atoms,so the parent alkane is butane.
$2$. Number the chain from the end that gives the lowest possible locant to the principal functional group $(-OH)$.
$3$. Numbering from right to left: $C_1$ is $CH_3$,$C_2$ is $CH(OH)$,$C_3$ is $CH$,$C_4$ is $CH_2$. The $-OH$ group is at position $2$ and the double bond is at position $3$.
$4$. The name is constructed as: (alkene part) + (alcohol part) = But-$3$-en-$2$-ol.
325
DifficultMCQ
The $IUPAC$ name of the following compound is :-
Question diagram
A
$1-$Ethyl-$2, 2-$dimethyl-$6-$cyclohexene
B
$2-$Ethyl-$1, 1-$dimethyl-$2-$cyclohexene
C
$1-$Ethyl-$6, 6-$dimethyl-$1-$cyclohexene
D
$2-$Ethyl-$3, 3-$dimethyl-$1-$cyclohexene

Solution

(B) $1$. Identify the principal functional group: The compound is a cyclic alkene. The double bond gets priority in numbering.
$2$. Number the ring: Start numbering from the double bond carbons such that the substituents get the lowest possible locants. Assign $C-1$ and $C-2$ to the double bond carbons.
$3$. If we assign $C-1$ to the carbon with the ethyl group and $C-2$ to the carbon with the two methyl groups,the locants are $1-$ethyl and $2, 2-$dimethyl.
$4$. If we assign $C-1$ to the carbon with the two methyl groups and $C-2$ to the carbon with the ethyl group,the locants are $1, 1-$dimethyl and $2-$ethyl.
$5$. According to the $IUPAC$ rule of lowest locant set,$(1, 1, 2)$ is preferred over $(1, 2, 2)$.
$6$. Therefore,the correct numbering gives the name $2-$Ethyl-$1, 1-$dimethylcyclohex-$2-$ene (or $2-$Ethyl-$1, 1-$dimethyl-$2-$cyclohexene).
326
DifficultMCQ
The $IUPAC$ name for the compound shown below is:
Question diagram
A
Propylene oxide
B
$1, 2-$Oxopropane
C
$1, 2-$Epoxypropane
D
$1, 2-$Propoxide

Solution

(C) The given compound is a cyclic ether containing a three-membered ring with one oxygen atom,known as an epoxide.
According to $IUPAC$ nomenclature rules for cyclic ethers,the prefix 'epoxy' is used followed by the name of the corresponding alkane.
The oxygen atom is bonded to the $1^{st}$ and $2^{nd}$ carbon atoms of the three-carbon chain.
Therefore,the correct $IUPAC$ name is $1, 2-$Epoxypropane.
327
DifficultMCQ
The $IUPAC$ name of the given compound is:
Question diagram
A
$1$-methoxy-$4$-aminobenzene
B
Aminophenyl methyl ether
C
$4$-Methoxyaniline
D
None of the above

Solution

(C) The structure consists of a benzene ring substituted with an amino group $(-NH_2)$ and a methoxy group $(-OCH_3)$ at the para $(1,4)$ positions.
According to $IUPAC$ nomenclature rules,the parent compound is aniline (benzeneamine) because the amino group takes priority over the ether group.
The carbon atom attached to the $-NH_2$ group is assigned position $1$.
Consequently,the methoxy group $(-OCH_3)$ at the para position is assigned position $4$.
Therefore,the correct $IUPAC$ name is $4$-methoxyaniline.
328
MediumMCQ
The $IUPAC$ name of neopentane is :-
A
$2-$Methyl propane
B
$2, 2-$Dimethyl butane
C
$2-$Methyl butane
D
$2, 2-$Dimethyl propane

Solution

(D) The structure of neopentane is $CH_3-C(CH_3)_2-CH_3$.
To determine the $IUPAC$ name:
$1$. Identify the longest carbon chain,which contains $3$ carbon atoms (propane).
$2$. Identify the substituents attached to the chain. There are two methyl groups attached to the second carbon atom.
$3$. Combining these,the $IUPAC$ name is $2, 2-$dimethylpropane.
Hence,the correct option is $D$.
329
DifficultMCQ
The correct $IUPAC$ name for the given structure is:-
Question diagram
A
Trans-$1,2$-chlorobromocyclopropane
B
Trans-$1$-bromo-$2$-chloropropane
C
Trans-$1$-bromo-$2$-chlorocyclopropane
D
cis-$1$-bromo-$2$-chlorocyclopropane

Solution

(C) $1$. Identify the parent chain: The structure is a cyclopropane ring.
$2$. Numbering: Number the ring starting from the substituent that comes first alphabetically. Here,$bromo$ $(Br)$ comes before $chloro$ $(Cl)$. So,assign $C-1$ to the carbon with $Br$ and $C-2$ to the carbon with $Cl$.
$3$. Stereochemistry: The $Br$ and $Cl$ atoms are on opposite sides of the ring plane,which indicates a $trans$ configuration.
$4$. Combining the parts: The name is $trans-1-bromo-2-chlorocyclopropane$.
330
DifficultMCQ
What will be the $IUPAC$ name of the compound formed when an allyl group and a neopentyl group are joined together?
A
$4,4-$dimethylpent$-1-$ene
B
$5,5-$dimethylhex$-1-$ene
C
$6-$methylhept$-1-$ene
D
$5-$methylhex$-1-$ene

Solution

(B) The allyl group is $CH_2=CH-CH_2-$.
The neopentyl group is $(CH_3)_3C-CH_2-$.
When these two groups are joined,the structure becomes $CH_2=CH-CH_2-CH_2-C(CH_3)_3$.
The longest carbon chain containing the double bond has $6$ carbons.
Numbering starts from the double bond: $CH_2(1)=CH(2)-CH_2(3)-CH_2(4)-C(CH_3)_2(5)-CH_3(6)$.
There are two methyl groups at the $5$th position.
Thus,the $IUPAC$ name is $5,5-$dimethylhex$-1-$ene.
331
MediumMCQ
The $IUPAC$ name of the compound shown in the image is:
Question diagram
A
$5-$Hydroxy benzene carboxylate
B
$3-$Hydroxy benzene carboxylate
C
$3-$Methoxy carbonyl benzene $-1-$ol
D
Methyl $3-$hydroxy benzoate

Solution

(D) $1$. Identify the principal functional group: The ester group $(-COOCH_3)$ has higher priority than the hydroxyl group $(-OH)$. Therefore,the parent compound is an ester of benzoic acid,which is named as a benzoate.
$2$. Numbering the ring: The carbon atom of the benzene ring attached to the ester group is assigned position $1$. The hydroxyl group is at the meta position relative to the ester group,which corresponds to position $3$.
$3$. Naming the substituents: The substituent on the oxygen of the ester is a methyl group,and the hydroxyl group is at position $3$.
$4$. Combine the parts: The name is methyl $3-$hydroxybenzoate.
332
DifficultMCQ
The correct structure of $6-$amino$-4-$hydroxycyclohex$-2-$ene$-1-$sulphonic acid is
A
Option A
B
Option B
C
Option C
D
Option D

Solution

(C) To determine the correct structure of $6-$amino$-4-$hydroxycyclohex$-2-$ene$-1-$sulphonic acid,we follow the $IUPAC$ nomenclature rules:
$1$. The principal functional group is the sulphonic acid group $(-SO_3H)$,which gets the lowest possible number,$1$.
$2$. The ring is a cyclohexene ring. The double bond starts at position $2$ (between $C_2$ and $C_3$).
$3$. The amino group $(-NH_2)$ is at position $6$.
$4$. The hydroxy group $(-OH)$ is at position $4$.
$5$. Looking at the options,structure $C$ correctly places the $-SO_3H$ at $C_1$,the double bond between $C_2$ and $C_3$,the $-NH_2$ at $C_6$,and the $-OH$ at $C_4$.
333
MediumMCQ
Which is incorrect numbering in the following compounds as per $IUPAC$ rules?
A
Hex$-1-$en$-5-$yne
B
Hex$-5-$en$-1-$yne
C
Hepta$-1,4-$dien$-6-$yne
D
Hepta$-1,4-$dien$-6-$yne

Solution

(D) According to $IUPAC$ nomenclature rules for unsaturated hydrocarbons containing both double and triple bonds:
$1$. The principal chain is selected such that it contains both the double and triple bonds,if possible.
$2$. Numbering is done such that the set of locants for the multiple bonds is as low as possible.
$3$. If there is a tie in the locant set (e.g.,$1, 5$ vs $1, 5$),the double bond is given preference over the triple bond for the lower number.
Analyzing the options:
- Option $A$: $CH_2=CH-CH_2-CH_2-C\equiv CH$. Numbering from left gives locants $1$ (ene) and $5$ (yne). This is correct.
- Option $B$: $CH\equiv C-CH_2-CH=CH-CH_3$. Numbering from right gives locants $1$ (yne) and $5$ (ene). This is correct.
- Option $C$: $CH_2=CH-CH_2-CH=CH-C\equiv CH$. Numbering from left gives locants $1, 4$ (enes) and $6$ (yne). This is correct.
- Option $D$: $CH_2=CH-CH_2-CH=CH-C\equiv CH$. The numbering shown in the image is $1, 2, 3, 4, 5, 6, 7$. The double bonds are at $1$ and $4$,and the triple bond is at $6$. However,the structure shown in the image for $D$ labels the triple bond at $6$ but the numbering sequence is inconsistent with the chain length or connectivity compared to standard $IUPAC$ rules for this specific structure. Specifically,the numbering in $D$ is $1, 2, 3, 4, 5, 6, 7$ where the double bond is at $4$ and $5$ in the image,which is incorrect as the double bond should be at $4$ and $5$ but the numbering $4-5$ is written as $4$ and $5$ on the same bond,which is invalid.
334
DifficultMCQ
The correct $IUPAC$ name of the compound is
Question diagram
A
$1-$Ethenylcyclohexa$-2,4-$diene
B
$5-$Ethenylcyclohexa$-1,3-$diene
C
$6-$Ethenylcyclohexa$-1,3-$diene
D
Cyclohexa$-2,4-$dienylethene

Solution

(B) $1$. Identify the principal functional group or the parent chain. Here,the cyclic ring (cyclohexadiene) is the parent chain.
$2$. Number the ring starting from the carbon attached to the ethenyl group as $1$,or such that the double bonds get the lowest possible locants.
$3$. If we start numbering from the carbon attached to the ethenyl group as $1$,the double bonds are at positions $2$ and $4$. This gives the name $1-$ethenylcyclohexa$-2,4-$diene.
$4$. However,according to $IUPAC$ rules for numbering,we should give the lowest locants to the double bonds. If we number the ring such that the double bonds are at $1$ and $3$,the ethenyl group will be at position $5$. This gives the name $5-$ethenylcyclohexa$-1,3-$diene.
$5$. Comparing the locant sets: $(1, 2, 4)$ vs $(1, 3, 5)$. The set $(1, 3, 5)$ is preferred as it provides lower locants for the double bonds.
$6$. Therefore,the correct $IUPAC$ name is $5-$ethenylcyclohexa$-1,3-$diene.
335
MediumMCQ
The given structure has the $IUPAC$ name:
Question diagram
A
$1-$Ethyl$-3,3-$dimethylcyclohexane
B
$3-$Ethyl$-1,3-$dimethylcyclohexane
C
$3-$Ethyl$-1,1-$dimethylcyclohexane
D
$3,3-$Dimethyl$-1-$ethylcyclohexane

Solution

(C) $1$. Identify the parent chain: The parent chain is a cyclohexane ring.
$2$. Identify substituents: There is an ethyl group $(-CH_2CH_3)$ and two methyl groups $(-CH_3)$ attached to the ring.
$3$. Numbering the ring: According to $IUPAC$ rules,we number the ring to give the lowest possible locants to the substituents. If we start numbering from the carbon with the two methyl groups as $1$,the substituents are at positions $1, 1,$ and $3$. If we start from the carbon with the ethyl group as $1$,the substituents are at $1, 3,$ and $3$.
$4$. Alphabetical order: Ethyl comes before methyl. Comparing the sets of locants $(1, 1, 3)$ vs $(1, 3, 3)$,the set $(1, 1, 3)$ is lower. However,we must also consider alphabetical priority when the locant sets are different. Assigning $1$ to the carbon with the ethyl group gives the name $1-$ethyl$-3,3-$dimethylcyclohexane. Assigning $1$ to the carbon with the two methyl groups gives $3-$ethyl$-1,1-$dimethylcyclohexane. Comparing the locants,$1, 1, 3$ is preferred over $1, 3, 3$. Therefore,the correct name is $3-$ethyl$-1,1-$dimethylcyclohexane.
336
DifficultMCQ
The $IUPAC$ name for the compound is
Question diagram
A
Cyclohexanoyl chloride
B
Cyclohexanecarbonyl chloride
C
$1$-Chlorocyclohexanal
D
Chlorocyclohexyl methanal

Solution

(B) The given structure is a cyclohexane ring attached to a carbonyl chloride group $(-COCl)$.
According to $IUPAC$ nomenclature rules,when a functional group like $-COCl$ is attached directly to an alicyclic ring,the carbon atom of the functional group is not included in the parent ring name.
Instead,the suffix $carbonyl \ chloride$ is used for the $-COCl$ group attached to the ring.
Therefore,the correct $IUPAC$ name is $Cyclohexanecarbonyl \ chloride$.
337
DifficultMCQ
The $IUPAC$ name of the given compound is:
Question diagram
A
$2, 6-$ Dimethylhepta$-2, 5-$dienoic acid
B
$3, 7-$ Dimethylhepta$-2, 5-$dienoic acid
C
$1-$ Hydroxy$-2, 6-$dimethylhepta$-2, 5-$dienone
D
None of these

Solution

(A) $1$. Identify the longest carbon chain containing the principal functional group (carboxylic acid). The chain has $7$ carbons,so the parent alkane is heptane.
$2$. Number the chain starting from the carboxylic acid carbon as $C-1$.
$3$. The double bonds are at positions $2$ and $5$. The suffix for the acid is $-oic$ acid,and for two double bonds,it is $-dienoic$ acid.
$4$. There are methyl groups at positions $2$ and $6$.
$5$. Combining these,the name is $2, 6-$ dimethylhepta$-2, 5-$dienoic acid.
338
DifficultMCQ
Select the structure with the correct numbering for the $IUPAC$ name of the compound.
A
Option A
B
Option B
C
Option C
D
Option D

Solution

(C) According to $IUPAC$ nomenclature rules for cyclic compounds containing multiple functional groups:
$1$. The principal functional group is given the lowest possible locant.
$2$. Between $-OH$ (alcohol) and $-SH$ (thiol),the $-OH$ group has higher priority.
$3$. Therefore,the carbon atom attached to the $-OH$ group should be numbered $1$.
$4$. The numbering should then proceed in a direction that gives the lowest possible locants to the other substituents and the double bond.
$5$. In structure $C$,the $-OH$ group is at position $1$,the double bond starts at position $2$,and the $-SH$ group is at position $4$. This follows the lowest locant rule for the double bond and substituents $(1, 2, 4)$.
$6$. Thus,structure $C$ represents the correct numbering.
339
DifficultMCQ
The structure of $3,4-$dimethylpent$-1-$en$-3-$ol is:
A
Option A
B
Option B
C
Option C
D
Option D

Solution

(A) To determine the structure of $3,4-$dimethylpent$-1-$en$-3-$ol,we follow these steps:
$1$. The parent chain is 'pent',which means it has $5$ carbon atoms.
$2$. The suffix '$-1-$en' indicates a double bond at the $1^{st}$ position.
$3$. The suffix '$-3-$ol' indicates a hydroxyl group $(-OH)$ at the $3^{rd}$ position.
$4$. The prefix '$3,4-$dimethyl' indicates two methyl groups $(-CH_3)$ attached at the $3^{rd}$ and $4^{th}$ positions.
$5$. Combining these,the structure is $CH_2=CH-C(OH)(CH_3)-CH(CH_3)-CH_3$.
$6$. Looking at the options,the structure in image $814-a898$ correctly represents this molecule: a $5-$carbon chain with a double bond at $C1$,an $-OH$ group at $C3$,and methyl groups at $C3$ and $C4$.
340
MediumMCQ
Which of the following $IUPAC$ name is correct for $OHC-CH_2-CH(CHO)-CH_2-CHO$?
A
$2-$Formylpentane$-1,3-$dial
B
$1,2,3-$Triformylpropane
C
$2-$Formylmethylbutane$-1,4-$dial
D
Propane$-1,2,3-$tricarbaldehyde

Solution

(D) According to $IUPAC$ rules,when three or more identical carbon-containing functional groups are directly attached to an unbranched carbon chain,the carbon atoms of these groups are not included in the parent chain.
For three $-CHO$ groups attached to a propane backbone,the suffix "tricarbaldehyde" is used.
The parent chain is propane ($3$ carbons).
Therefore,the correct $IUPAC$ name is Propane$-1,2,3-$tricarbaldehyde.
341
MediumMCQ
Which is the correct $IUPAC$ name for: $CH_3-CH(CH_2-CH_3)-CH_2-Br$?
A
$1$-bromo-$2$-ethylpropane
B
$1$-bromo-$2$-ethyl-$2$-methylethane
C
$1$-bromo-$2$-methylbutane
D
$2$-methyl-$1$-bromobutane

Solution

(C) The given structure is $CH_3-CH(CH_2-CH_3)-CH_2-Br$.
Expanding the ethyl group,we get $CH_3-CH_2-CH(CH_3)-CH_2-Br$.
The longest carbon chain containing the bromine atom has $4$ carbon atoms,so the parent alkane is butane.
Numbering the chain from the end closer to the bromine atom,we get $Br$ at $C1$ and a methyl group at $C2$.
According to $IUPAC$ rules,substituents are listed in alphabetical order (bromo before methyl).
Therefore,the $IUPAC$ name is $1$-bromo-$2$-methylbutane.
Solution diagram
342
DifficultMCQ
The $IUPAC$ name of the following compound is:
Question diagram
A
$6-$Bromo$-2-$chlorocyclohexene
B
$3-$Bromo$-1-$chlorocyclohexene
C
$1-$Bromo$-3-$chlorocyclohexene
D
$2-$Bromo$-6-$chlorocyclohexene

Solution

(B) $1$. In cyclic alkenes,the double bond is given priority in numbering,starting from the carbons of the double bond such that substituents get the lowest possible locants.
$2$. Assign position $1$ to the carbon attached to the chlorine atom and position $2$ to the other carbon of the double bond.
$3$. Following this,the bromine atom is at position $3$.
$4$. Thus,the correct $IUPAC$ name is $3-$bromo$-1-$chlorocyclohexene.
343
DifficultMCQ
The $IUPAC$ name of the given compound is:
Question diagram
A
$2-$Bromo$-1-$methylcyclohexene
B
$6-$Bromo$-1-$methylcyclohexene
C
$1-$Bromo$-2-$methylcyclohexene
D
$1-$Bromo$-2-$methylcyclohex$-2-$ene

Solution

(B) $1$. In the given cyclic compound,the double bond is present between $C1$ and $C2$. According to $IUPAC$ rules,the double bond should be given priority and numbered such that it gets the lowest possible locants ($1$ and $2$).
$2$. We start numbering from the carbon atom of the double bond that allows the substituent to have the lowest possible number.
$3$. If we number the double bond carbons as $1$ and $2$,the methyl group is at position $1$ and the bromine atom is at position $6$.
$4$. Thus,the correct numbering gives the $6-$bromo and $1-$methyl substituents.
$5$. Combining these,the name is $6-$Bromo$-1-$methylcyclohexene.
344
MediumMCQ
The $IUPAC$ name of the compound is:
Question diagram
A
$4-$Methylcyclopent$-1-$en$-2-$ol
B
$5-$Methylcyclopent$-2-$en$-1-$ol
C
$2-$Methylcyclopent$-4-$en$-1-$ol
D
$3-$Methylcyclopent$-1-$en$-2-$ol

Solution

(B) $1$. Identify the principal functional group: The $-OH$ group has higher priority than the double bond,so it gets the lowest possible locant,$1$.
$2$. Number the ring: Start numbering from the carbon attached to the $-OH$ group as $1$. To give the double bond the lowest locant,proceed towards the double bond.
$3$. Numbering path: If we number clockwise,the double bond starts at $C-2$. If we number counter-clockwise,the double bond starts at $C-4$. Thus,clockwise is correct.
$4$. Assign locants: The $-OH$ is at $C-1$,the double bond starts at $C-2$,and the methyl group is at $C-5$.
$5$. Construct the name: The parent chain is cyclopentene. Combining these,we get $5-$methylcyclopent$-2-$en$-1-$ol.
345
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

(C) 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 position $3$ and a triple bond at position $5$.
$3$. Substituents are an ethyl group at position $3$,a hydroxy group at position $2$,and a methyl group at position $4$.
$4$. Constructing the chain: $C1(COOH)-C2(OH)-C3(Et)=C4(Me)-C5\#C6$.
$5$. Comparing this with the given options,the structure corresponds to the one shown in the solution image.
346
DifficultMCQ
The correct $IUPAC$ name of the given compound is:
Question diagram
A
$2-$Ethyl$-3-$methylbut$-2-$ene$-1,4-$dioic anhydride
B
$3-$Ethyl$-2-$methylbut$-2-$enedioic anhydride
C
$2-$Ethyl$-3-$methyl$-1,4-$diketobut$-2-$enoic anhydride
D
$2-$Ethyl$-3-$methylcyclopentanoxy$-1,4-$dione

Solution

(A) The given compound is a cyclic anhydride derived from a dicarboxylic acid.
$1$. The parent chain is a four-carbon chain containing a double bond,which is $but-2-ene$.
$2$. The anhydride functional group is formed from the $1,4-$dicarboxylic acid positions.
$3$. Numbering starts from one of the carbonyl carbons. Following alphabetical order for substituents,the ethyl group at position $2$ and the methyl group at position $3$ gives the name $2-$Ethyl$-3-$methylbut$-2-$ene$-1,4-$dioic anhydride.
347
MediumMCQ
The $IUPAC$ name of succinic acid is:
A
$Butane-1,4-dioic$ $acid$
B
$Propane-1,3-dioic$ $acid$
C
$Ethane-1,2-dioic$ $acid$
D
$Pentane-1,5-dioic$ $acid$

Solution

(A) Succinic acid has the structural formula $HOOC-CH_2-CH_2-COOH$.
The longest carbon chain containing both carboxyl groups consists of $4$ carbon atoms.
Therefore,the $IUPAC$ name is $Butane-1,4-dioic$ $acid$.
348
MediumMCQ
The $IUPAC$ name of the compound $CH_2=CH-CH(CH_3)_2$ is
A
$1,1-$dimethyl$-2-$propene
B
$2-$vinylpropene
C
$3-$methylbut$-1-$ene
D
$1-$isopropylethene

Solution

(C) The structure of the compound is $CH_2=CH-CH(CH_3)_2$.
To name this compound according to $IUPAC$ rules:
$1$. Select the longest carbon chain containing the double bond. The longest chain has $4$ carbon atoms,so the parent alkane is butane.
$2$. Number the chain from the end that gives the lowest locant to the double bond. Starting from the left,the double bond starts at carbon $1$.
$3$. Identify the substituent. There is a methyl group at position $3$.
$4$. Combining these,the name is $3-$methylbut$-1-$ene.
Hence,the correct option is $(C)$.
349
DifficultMCQ
The correct $IUPAC$ name of the given compound is:
Question diagram
A
$3-$Ethanoyloxycyclopent$-4-$ene carboxylic acid
B
$4-$Ethanoyloxycyclopent$-2-$ene carboxylic acid
C
$4-$Ethanoyloxycyclopent$-3-$ene carboxylic acid
D
$4-$Ethanoyloxycyclopent$-1-$ene$-5-$carboxylic acid

Solution

(B) $1$. Identify the principal functional group: The carboxylic acid group $(-COOH)$ has higher priority than the ester group $(-O-CO-CH_3)$. Thus,the parent chain is a cyclopentene carboxylic acid.
$2$. Numbering the ring: Start numbering from the carbon attached to the $-COOH$ group as $C-1$. To give the double bond the lowest possible locant,proceed towards the double bond. Thus,the double bond starts at $C-2$.
$3$. Identify substituents: The $-O-CO-CH_3$ group is an ethanoyloxy group (or acetoxy group) located at the $C-4$ position.
$4$. Combine the parts: The name is $4-$ethanoyloxycyclopent$-2-$ene$-1-$carboxylic acid,which is commonly written as $4-$ethanoyloxycyclopent$-2-$ene carboxylic acid.
350
AdvancedMCQ
Which of the following $IUPAC$ names is incorrect?
A
Option A
B
Option B
C
Option C
D
Option D

Solution

(A) Let us analyze each option based on $IUPAC$ nomenclature rules:
$A$. For $1,5$-dimethylcyclopentene,the double bond gets priority. Numbering starts from the double bond such that substituents get the lowest possible locants. The correct name is $1,2$-dimethylcyclopentene.
$B$. For $3,4$-dimethylpent-$1$-en-$3$-ol,the principal functional group is alcohol $(-OH)$,which gets the lowest locant. The chain is numbered starting from the end closer to the $-OH$ group. The name is correct.
$C$. For $6$-bromo-$3,3$-dimethylcyclohexene,the double bond is between $C1$ and $C2$. Numbering starts from the double bond towards the substituent. The name is correct.
$D$. For $5$-hydroxycyclopent-$2$-en-$1$-ol,the principal functional group is $-OH$. The double bond is between $C1$ and $C2$ (or $C2$ and $C3$ depending on numbering). The correct $IUPAC$ name is cyclopent-$2$-ene-$1,4$-diol.
Comparing the options,the name in option $A$ is incorrect as it should be $1,2$-dimethylcyclopentene.

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