Organic Nomenclature practice

Love Chemistry Organically!

By Royal Society of
chemistry
With Dr. Saif Soliman
 Practice  Problems  on  Alkane  Nomenclature  -­‐  Answers  

CH3
CH2

1   CH
2-­‐methylbutane  
CH3 CH3
 
CH3
CH2
2   4-­‐ethylheptane  
CH2 CH CH2
CH3 CH2 CH2 CH3
 
CH3

CH2 CH CH2

3   CH3 CH2 CH CH3

3-­‐ethyl-­‐4-­‐methylheptane  
CH2

CH3
 
CH2 CH2 CH2
CH3 CH CH CH3

4   CH3 CH2 5-­‐ethyl-­‐3-­‐methyloctane  

CH2

CH3
 
 

5   3-­‐ethyl-­‐2,2,5-­‐trimethylhexane  

6   5-­‐sec-­‐butyl-­‐2,7-­‐dimethylnonane  

7   4-­‐chloro-­‐5-­‐ethyloctane  
Cl

8   5-­‐tert-­‐butyl-­‐4-­‐ethyl-­‐3-­‐methyloctane  

 
 
1,3-­‐diisopropyl-­‐2,2-­‐
9  
dimethylcyclopentane  

 
  

Draw  structural  formulas  for  each  of  the  following.  

9)    4-­‐ethyloctane  

10)    2-­‐methylnonane  

11)    3,3-­‐dimethylpentane  

12)      3-­‐ethylpentane  

13)    3-­‐ethyl-­‐2-­‐methylheptane  

14)    3-­‐ethyl-­‐4-­‐(1-­‐methylpropyl)-­‐2,2-­‐dimethyloctane  

Prepared  by  José  Laboy  

 Chemistry 0871 Learning Centre

Naming Organic Compounds Practice

EXERCISES
A. Identify the class of the following compounds. For any alkanes, alkenes, alkynes,
aromatic compounds, carboxylic acids or alcohols, provide the IUPAC name of the
molecule. For the four special monosubstituted benzenes, use the common name.
1) I 8)
Br CH3

2) H2C CH3 9) H2C CH3

H3C CH CH2CH2 CH3 H3C C C CH CHCH3
H3C

3) O 10) O
H3C C CH2 CH3 H3C CH2CH2 CH2 CH

4) Cl CH3 11) O
H3C CH CH C CH2 CH2 CH2 CH3 HO C CH2CH2CH2 CH2 CH3
CH3 CH2CH3

5) CH 2CH 3 12) OH
CH 2CH 3 H3C CH CH CH CH3
CH3 H3C

6) CH3 13) H3C

H2C CH CH CH2 H3C C C C CH3
CH3 CH3 CH2CH3

7) O 14) H2C CH3

H3C CH C O CH3 H3C CH CH O CH2 CH3

CH3 CH3

Authored by Emily Simpson

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B. Draw the structural formulas for the following compounds:

1) 1-pentene 7) 4-methylhexanoic acid

2) 2-methyl-3-heptyne 8) 2,3-dichloro-4-ethyl-2-hexene

3) 3-ethyl-4,5-dimethylpentane 9) 2,4-dinitrotoluene

4) 2-ethyl-1-pentanol 10) 3-ethyl-2,3-dimethyl-2-pentanol

5) m-bromophenol 11) 5-chloro-4-methyl-3-heptanone

6) 3,3,6,6-tetraethyl-4-octyne 12) 3-phenyl-1-propyne

C. Draw all possible open-chain structures for the following molecular formulas and
name them:
1) C5H12

2) C5H10

3) C3H8O

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SOLUTIONS
A. (1) aromatic compound: iodobenzene (2) alkane: 3-methylhexane (3) ketone
(4) alkane/alkyl halide: 3-chloro-4-ethyl-2,4-dimethyloctane (5) aromatic compound:
o-diethylbenzene or ortho-diethylbenzene (6) alkene: 3-methylpentene (7) ester
(8) aromatic compound: p-bromotoluene or para-bromotoluene (9) alkyne:
4-ethyl-5-methyl-2-hexyne (10) aldehyde (11) carboxylic acid: hexanoic acid
(12) alcohol: 2,4-dimethyl-3-pentanol (13) alkene: 2,4,4-trimethyl-2-hexene
(14) ether

B. (1) H2C=CH−CH2−CH2−CH3 (2) H3C−CH−C≡C−CH2−CH2−CH3 (3) CH3

CH3 H3C−CH2−CH−CH−CH2−CH3
CH2−CH3
(4) HO−CH2−CH−CH2−CH2−CH3 (5) OH (6) H3C−CH2 CH2−CH3
CH2−CH3 H3C−CH2−C−C≡C−C−CH2−CH3
Br H3C−CH2 CH2−CH3
(7) O=C−CH2−CH2−CH−CH2−CH3 (8) Cℓ (9) CH3
OH CH3 H3C−C=C−CH−CH2−CH3 NO2
Cℓ CH2−CH3
NO2
(10) H3C CH3 (11) O (12)
H3C−C−C−CH2−CH3 H3C−CH2−C−CH−CH−CH2−CH3
HO CH2−CH3 H3C Cℓ HC≡C−CH2

C. (1) pentane 2-methylbutane 2,2-dimethylpropane

H3C−CH2−CH2−CH2−CH3 H3C−CH2−CH2−CH3 CH3
CH3 H3C−CH2−CH3
CH3

(2) 1-pentene 2-pentene 2-methyl-1-butene

H2C=CH−CH2−CH2−CH3 H3C−CH=CH−CH2−CH3 H2C=C−CH2−CH3
CH3

3-methyl-1-butene 2-methyl-2-butene
H2C=CH−CH−CH3 H3C−C=CH−CH3
CH3 CH3

(3) 1-propanol 2-propanol methoxyethane (methyl ethyl ether)

HO−CH2−CH2−CH3 H3C−CH−CH3 H3C−O−CH2−CH3
OH

This work is licensed under a Creative Commons Attribution 4.0 International License 3
Name the following compounds:

1. 12.

2.

13.

3.

14.

4.

5.
15.

6.

16. O
H–C–CH2–CH2–CH–CH3
7.
NH2

8. 17.

9.

18.

10.

11. 19.
Name the following compounds:

Answers

1) propoxypentane (pentoxypropane is OK, but it’s better to name the smaller R group first)
2) 3-bromobutanoic acid
3) butanone
4) 2-chloro-1-propanol
5) 2-pentyne
6) 3,3-dimethylpentane
7) 1-bromo-1,2-dichloropropane
8) 5-ethyl-2-methyl-3-heptyne
9) 3-hexene
10) 4-ethyl-2-methyl-nonane
11) 2,3,3-trimethylhexane
12) 2-methyl-2-propanol or just methyl-2-propanol
13) 2-butanol
14) 3-ethyl-1-hexanol
15) 4-phenyloctane
16) 4-aminopentanal
17) ethanoic acid (also known as acetic acid or vinegar)
18) 3-methylhexanoic acid
19) 2-ethoxypentane
 C h e m g u id e – q u e s t i o n s

NAMING ORGANIC COMPOUNDS: 1

Important: These questions cover all the compounds on this page. If you are doing this sensibly,
you will only be looking at one or two types of compounds at a time. I have written the questions
so that you can just answer those you are currently interested in. Later questions will, however,
assume that you are confident with things covered in earlier ones.

1. Alkanes

a) Draw the structures for the following compounds:

(i) 2-methylpropane

(ii) 2,3-dimethylpentane

(iii) 3-ethyl-2,4-dimethylhexane

b) Name the following compounds, all of which have the molecular formula C6H14:
CH3
CH3CH2CH2CH2CH2CH3 CH3CHCH2CH2CH3 CH3CHCHCH3
CH3 CH3
A B C

CH3 CH3
CH3CH2CHCH2CH3 CH3CCH2CH3
CH3
D E

2. Cycloalkanes

a) Draw the structures for the following compounds:

(i) cyclobutane

(ii) cyclopentane

(iii) 1,3-dimethylcyclohexane

b) Name these compounds: CH2

CH2 CH2

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 C h e m g u id e – q u e s t i o n s

3. Alkenes

a) Draw the structures for the following compounds:

(i) but-2-ene

(ii) 2-methylbut-2-ene

(iii) 2,3-dimethylbut-2-ene

(iv) 3-ethyl-2-methylpent-1-ene

b) Name these compounds:

(i) CH3C CH2

CH3

(ii) CH3
CH3CHCH CCH3
CH3

4. Compounds containing halogens

a) Draw the structures for the following compounds:

(i) tetrachloromethane

(ii) 1,1-dichloroethene

(iii) 1,2-dibromo-2-methylbutane

(iv) 1,2-dibromocyclohexane

b) Name these compounds:

(i) CH3CH2CH2I

(ii) Br
CH3CHCHCH3
Br

(iii) CH3CH2CH CCH2F

CH3

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 C h e m g u id e – q u e s t i o n s

5. Alcohols

a) Draw the structures for the following compounds:

(i) ethanol

(ii) 2-methylpropan-2-ol

(iii) butan-2-ol

(iv) but-2-en-1-ol

b) Name these compounds:

(i) CH3CH2CH2CH2CH2OH

(ii) CH3
CH3CH2CHCH2OH

(iii) CH3
CH3CHCH2CH2OH

(iv) CH3
CH3CCH2OH
CH3
6. Aldehydes and ketones

a) Draw the structures for the following compounds:

(i) ethanal

(ii) butanone (also known as butan-2-one, but the 2 is unnecessary and is often left out)

(iii) 2-methylpropanal

(iv) 3-methylpentan-2-one

b) Name these compounds:

O
(i)
HC
H

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C h e m g u id e – q u e s t i o n s

(ii)
CH3
CH3CCHCH2CH3
O
O
(iii) CH3C
CH2CH2CH3

(iv) CH3 O
CH3CCH2C
CH3 H

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 Chemguide – answers

NAMING ORGANIC COMPOUNDS: 1

1. Alkanes

a)
(i) CH3
CH3CHCH3

(You shouldn't really have got this one wrong. Unless you made a careless mistake (like putting too
many or too few hydrogens on the middle carbon), if you got it wrong, re-read the bit about naming
alkanes and then look at these questions again.)

(ii) CH3
CH3CHCHCH2CH3
CH3

(It doesn't matter whether you have drawn the various groups pointing up or down, or if you have
flipped the molecule end-to-end by numbering from the right-hand end of the longest chain.)

(iii) CH3 CH3

CH3CHCHCHCH2CH3
CH2CH3

(Again, it doesn't matter whether you have numbered from the right-hand end (and so flipped the
molecule end-to-end), or whether the various side-groups point up or down.)

b) A is easy. It is a 6-membered chain (hex) with no carbon-carbon double bonds (an). The
molecule is just hexane.

In B, the longest chain has 5 carbons (pent) with no carbon-carbon double bonds (an). There is a
methyl group on the number 2 carbon. The molecule is 2-methylpentane. (4-methylpentane is
wrong. You number in such away as to get the smallest numbers in the name.)

In C, the longest chain has 4 carbons (but) with no carbon-carbon double bonds (an). There are two
methyl groups on the number 2 and 3 carbons. The molecule is 2,3-dimethylbutane.

In D, the longest chain has 5 carbons (pent) with no carbon-carbon double bonds (an). There is a
methyl group on the number 3 carbon. The molecule is 3-methylpentane.

In E, the longest chain has 4 carbons (but) with no carbon-carbon double bonds (an). There are two
methyl groups both on the number 2 carbon. The molecule is 2,2-dimethylbutane. (Even if they are
on the same carbon, you must write both numbers, and include the “di”. It is 2,2- rather than 3,3-
in order to get the smallest numbers in the name.)

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 Chemguide – answers

2. Cycloalkanes

a) (i) CH2 CH2

CH2 CH2

(ii)

(There is a CH2 group at each corner. In an exam, you would, of course, write them in unless you
were asked for the skeletal formula. It is just much quicker for me to draw a pentagon than all the
individual CH2 groups.)

(iii) CH3

CH
CH2 CH2

CH2 CH
CH2 CH3

(Again it would have been quicker for me to draw a skeletal formula, but it is important that you
can see how many hydrogens there are attached to each carbon. It is easy to put an extra hydrogen
atom by mistake on the carbons with the methyl groups attached. It doesn't matter where you attach
these groups around the ring as long as they are spaced as shown – attached to the next-but-one
carbon atoms.)

b) These are cyclopropane and methylcyclopentane. There is no need to put a number in the second
name, because it makes no difference whatsoever which corner you attach the CH3 group to. You
would just be rotating the molecule.

3. Alkenes

a) (i) CH3CH CHCH3

(ii) CH3CH CCH3

CH3
(It doesn't matter if you have numbered from the left-hand end, and attached the methyl group to the
second carbon from the left rather than the second from the right. The only difference is that the
molecule will have been flipped end-to-end.)

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 Chemguide – answers

(iii) CH3
CH3C CCH3
CH3

(It doesn't matter whether your CH3 groups point up or down. Make sure that you haven't drawn
any hydrogens on the carbons with the methyl groups attached.)

(iv) CH2CH3
CH3CH2CHC CH2
CH3

(Again, you may well have numbered this starting from 1 at the left-hand end so that you have
drawn the molecule flipped end-to-end. It doesn't matter whether your methyl and ethyl groups
point up or down. Make sure that you haven't put a hydrogen on the number 2 carbon.)

b) (i) Methylpropene. You don't need the number 2 because the methyl group can't be attached
anywhere else. If you put it on one of the end carbons, your longest chain would then have 4
carbons, and so the name would be based on butene.

(ii) The longest chain is 5 carbons (pent) with a double bond (en). The double bond starts on
the number 2 carbon. So this is 2,4-dimethylpent-2-ene. If you started numbering from the other
end, your total of the numbers in the name would be bigger. So it's not 2,4-dimethylpent-3-ene.
(Not that it matters hugely. The strictly incorrect name still enables you to draw the right structure,
which is all that really matters.)

4. Compounds containing halogens

a) (i) Cl
Cl C Cl
Cl
(ii) CH2 CCl2

(You could put the two chlorines on the other carbon atom if you wanted to.)

(iii) CH3
CH2CCH2CH3
Br Br

(As always, you could equally well have started numbering from the right-hand end, and drawn the
molecule flipped end-to-end. You could also have drawn the end bromine in line with the rest of
the chain as BrCH2- or -CH2Br if you had drawn it at the other end.)

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 Chemguide – answers

(iv) Br

CH Br
CH2 CH

CH2 CH2
CH2

(It doesn't matter where you put the two bromines around the ring as long as they are next door to
each other. Make sure that you haven't put too many hydrogens on the carbons with the bromines
attached.)

b) Name these compounds:

(i) 1-iodopropane

(ii) 2,3-dibromobutane

(iii) 1-fluoro-2-methylpent-2-ene (Count it as wrong if you have written the fluoro bit as
“flouro”!)

5. Alcohols

a) (i) CH3CH2OH

(ii) CH3
CH3CCH3
OH

(It would be fairly common to write this rotated through 90° so that the main 3-carbon chain was
vertical and the OH group on the right-hand side.)

(iii) CH3CHCH2CH3
OH
(You could just as well have written the OH on the second carbon from the right.)

(iv) CH3CH CHCH2OH

(In this case, the OH group would almost invariably be written on the right-hand end. If you wrote
it on the left-hand end, don't worry about it. It is something you could only know with experience.)

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 Chemguide – answers

b) (i) pentan-1-ol

(ii) 2-methylbutan-1-ol

(iii) 3-methylbutan-1-ol

(iv) 2,2-dimethylpropan-1-ol

6. Aldehydes and ketones

a) (i) O
CH3C
H

(The aldehyde group is always best shown like this, giving an impression of the way the various
bonds are arranged in space.)

(ii) CH3CCH2CH3

O
(It doesn't matter which of the two middle carbons you attach the oxygen to – it depends on which
end you start numbering from. You might also draw this as:
O
CH3C
CH2CH3

. . . perhaps also showing the bond between the first CH3 group and the C=O group as a line as
well.)

(iii) O
CH3CHC
CH3 H

(iv) You could use one of these structures, both of which are correct, or some variation on
them:
O CH3
CH3C CH3CCHCH2CH3
CHCH2CH3
O
CH3

If you find this confusing, don't worry about it. With increasing experience, you will get to
recognise different ways of drawing the same structure without too much difficulty.

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Chemguide – answers

b) (i) methanal

(ii) 3-methylpentan-2-one.

(iii) pentan-2-one

(iv) 3,3-dimethylbutanal. The aldehyde group has to be on the end, and is automatically
given the number 1 carbon – you don't need to include that in the name.

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