isomers of C7H14  

Advanced level organic chemistry PART 14.7: Structural isomers of molecular formula C7H14

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Doc Brown's Advanced Chemistry: Part 14.7 including isomers of the given molecular formula C7H14

53 Selected constitutional-structural isomers and stereoisomers of molecular formula C7H14

[Author ©  Dr Phil Brown GRIC, PhD: Doc Brown's advanced level organic chemistry exam revision notes suitable for students of UK advanced level chemistry courses, IB advanced chemistry & US K12 grades 11-12 and AP honors chemistry courses: Molecular spectroscopy and analysing the isomers of C7H14 [page updated RE-EDIT]


Sub-index for this page on the isomers of C7H14

(A) Introduction to the isomers of molecular formula C7H14

(B) Details of 53 selected isomers of C7H14

(C) Extra information on the  isomers of C7H14

(D) Learning objectives for isomerism of molecular formula C7H14

(E) Practise exam questions on the isomers of C7H14


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(A) Introduction to 53 examples of non-cyclic alkene and cycloalkane structural isomers of molecular formula C7H14

structural skeletal formula constitutional isomers of C7H14 aliphatic alkenes alicyclic cycloalkanes cyclic alkanes stereoisomers E/Z isomers R/S isomers of molecular formula C7H14 hydrocarbon compounds

Percent composition of C7H14 based on atomic masses C = 12.01  H = 1.01  and  Mr(C6H12) = 98.21

Element composition (to two dp): carbon = 85.60%     hydrogen = 14.40%

Empirical formula = CH2 and molecular formula = C7H14

Structural isomerism  - isomers based on different connectivity's of the constituent atoms, so cannot be spatially identical (but can be defined as having the same shape).

This includes (a) carbon chain variation (usually need a minimum of 4 atoms), (b) change in position of a C atoms in the ring). or functional group and (c) functional group isomerism where the atoms have a different connectivity configuration, usually with significant differences in chemical and physical properties e.g.

(a) chain variation in the alkenes e.g. linear and branched, many varieties cyclic alkanes (C3-7)

(b) position of the alkene group in the open chain aliphatic alkenes,

(c) they are all examples of unsaturated open chain aliphatic alkenes versus saturated alicyclic cycloalkane molecules.

Stereoisomerism - isomers based on the same connectivity of the atoms (same constitutional formula), but in some way, they are 2D or 3D spatially different non-superimposable images (e.g. E/Z 'geometrical' isomers or mirror image R/S 'optical' isomers)

This is where molecules have the same basic constitutional structural formula, but isomers differ in the 2D/3D arrangement of the atoms.

For stereoisomers, the (CIP) abbreviation means the IUPAC Cahn-Ingold-Prelog priority order rule for assigning E/Z (geometrical) and R/S (optical) stereoisomers.

E/Z stereoisomerism was called 'geometrical isomerism' e.g. cis and trans isomers of alkenes or disubstituted cyclic alkanes where, due to restricted rotation, there are 2D/3D spatial variations that are not mirror images and not super imposable.

There are examples in the alkenes AND in the disubstituted cycloalkane ring molecules.

R/S stereoisomerism was called 'optical isomerism', the pairs of isomers are called enantiomers which are 3D non-superimposable mirror image forms of the same molecule (enantiomers). The molecule must have a chiral centre (a stereocentre), that is an asymmetric carbon atom with four different atoms/groups attached to it.

R/S optical isomerism is seen in both alkenes AND disubstituted cycloalkane ring molecules, AND, in the case of the latter, you can get complex stereoisomerism with the overlap of both E/Z and R/S isomers - university level analysis required.

NOTE

There are at least 53 constitutional-structural isomers based on C7H14, excluding E/Z and R/S isomers, all 53 of them are illustrated below, together with their E/Z (cis/trans) isomers if applicable.

There are at least 26 pairs of E/Z or R/S stereoisomers, so the total distinct unique isomers for C7H14 is at least 66 !!!

I've identified 25 alkenes, (open chain aliphatic compounds) giving their constitutional-structural formulae, but excluding E/Z and R/S isomers.

There are carbon chain isomers and positional isomers of the C=C double bond.

I've identified 28 cycloalkanes (alicyclic compounds) based on cycloheptane, cyclohexane, cyclopentane, cyclobutane and cyclopropane.

Apart from cycloheptane, they all involve alkyl substituents in the ring.

There are functional group isomers alkene/cycloalkane, and lots of R/S ('optical') and E/Z isomers (cis/trans geometrical stereoisomers)

There are also brief notes on the number of principal 1H NMR spectra chemical shift and proton ratio data and the number of principal 13C NMR resonances for the isomers of C7H14.


(B) Details of 53 selected constitutional isomers and stereoisomers of molecular formula C7H14

Some images are duplicated as I'm developing a new database of skeletal formulae.

Firstly the open chain unsaturated aliphatic alkenes with one C=C double bond.

All of these open chain aliphatic alkenes will show a characteristic, relatively strong and sharp absorption band in their infrared spectrum, around wavenumbers 1640-1680 cm-1 for the stretching vibration of the C=C bond.

(1) hept-1-ene, alkenes structure and naming (c) doc b, alkenes structure and naming (c) doc b, isomers of C7H14 heptene alkenes structure and naming (c) doc b (1-heptene)

hept-1-ene 1-heptene structural skeletal formula isomer of C7H14 , skeletal formula

A linear alkene with no E/Z 'geometrical' or R/S 'optical' stereoisomers

Number of low resolution NMR chemical shift δ signal peaks: 7 1H and 7 13C (email if disagree?)

1H NMR ratio of integrated proton peak areas: 3 : 2 : 2 : 2 : 2 : 1 : 2 (for equivalent protons)

BUT, for the 'end' =CH2 alkene protons, you can get two chemical shifts close together, if there are two different groups attached to the other carbon of the C=C bond i.e. R"R'C=CH2 where R" and R' are different. This causes the two =CH2 protons to experience slightly different fields.

Index of 1H NMR spectra organic compounds and Index of 13C NMR spectra organic compounds

There are no E/Z isomers of -1-enes because there are two identical groups (H) attached to the same carbon of the end double bond.

 

(2) hept-2-ene, alkenes structure and naming (c) doc b, alkenes structure and naming (c) doc b , abbreviated structural formula

(Z)-hept-2-ene, (Z)-2-heptene (E)-hept-2-ene. (E)-2-heptene structural skeletal formula isomer of C7H14 , skeletal formula

has two E/Z isomers: Z/cis- alkenes structure and naming (c) doc b , (Z)-hept-ene, (Z)-2-heptene

and E/trans- (c) doc b , (E)-hept-2-ene. (E)-2-heptene

(cis and trans 2-heptene)

From the CIP assignment priority rule for E/Z isomers: 6C  >  1H

CIP rule for the four atoms/groups around the >C=C< double bond

Number of low resolution NMR chemical shift δ signal peaks: 7 1H and 7 13C (email if disagree?)

1H NMR ratio of integrated proton peak areas: 3 : 2 : 2 : 2 : 1 : 1 : 3 (for equivalent protons)

 

(3) hept-3-ene, alkenes structure and naming (c) doc b, alkenes structure and naming (c) doc b

(Z)-hept-3-ene, (Z)-3-heptene (E)-hept-3-ene, (E)-3-heptene structural skeletal formula isomer of C7H14 , skeletal formula

has two E/Z geometrical isomers: Z/cis- alkenes structure and naming (c) doc b , (Z)-hept-3-ene, (Z)-3-heptene

and E/trans- alkenes structure and naming (c) doc b , (E)-hept-3-ene, (E)-3-heptene

(cis and trans 3-heptene)

From the CIP assignment priority rule for E/Z isomers: 6C  >  1H about the C=C bond.

CIP rule for the four atoms/groups around the >C=C< double bond

Number of low resolution NMR chemical shift δ signal peaks: 7 1H and 7 13C (email if disagree?)

1H NMR ratio of integrated proton peak areas: 3 : 2 : 2 : 1 : 1 : 2 : 3 (for equivalent protons)

 

(4) 2-methylhex-1-ene, alkenes structure and naming (c) doc balkenes structure and naming (c) doc b (2-methyl-1-hexene)

2-methylhex-1-ene 2-methyl-1-hexene structural skeletal formula isomer of C7H14 , skeletal formula

A branched alkene with no E/Z 'geometrical' or R/S 'optical' stereoisomers

Number of low resolution NMR chemical shift δ signal peaks: 6 1H and 7 13C (email if disagree?)

1H NMR ratio of integrated proton peak areas: 3 : 2 : 2 : 2 : 2 : 3 (for equivalent protons)

BUT, for the 'end' =CH2 alkene protons, you can get two chemical shifts close together, if there are two different groups attached to the other carbon of the C=C bond i.e. R"R'C=CH2 where R" and R' are different. This causes the two =CH2 protons to experience slightly different fields.

 

(5) 3-methylhex-1-ene, alkenes structure and naming (c) doc b , alkenes structure and naming (c) doc b  (3-methyl-1-hexene)

3-methylhex-1-ene 3-methyl-1-hexene structural skeletal formula isomer of C7H14 , skeletal formula, R/S 'optical' isomers (enantiomers)

Stereoisomers as carbon atom C3 is chiral (asymmetric, stereocentre)

Number of low resolution NMR chemical shift δ signal peaks: 7 1H and 7 13C (email if disagree?)

1H NMR ratio of integrated proton peak areas: 3 : 2 : 2 : 3 : 1 : 1 : 2 (for equivalent protons)

BUT, for the 'end' =CH2 alkene protons, you can get two chemical shifts close together, if there are two different groups attached to the other carbon of the C=C bond i.e. R"R'C=CH2 where R" and R' are different. This causes the two =CH2 protons to experience slightly different fields.

 

(6) 4-methylhex-1-ene, alkenes structure and naming (c) doc b , alkenes structure and naming (c) doc b  (4-methyl-1-hexene)

4-methylhex-1-ene 4-methyl-1-hexene structural skeletal formula isomer of C7H14 , skeletal formula, R/S 'optical' isomers (enantiomers)

Stereoisomers as carbon atom C4 is chiral (asymmetric, stereocentre)

Number of low resolution NMR chemical shift δ signal peaks: 7 1H and 7 13C (email if disagree?)

1H NMR ratio of integrated proton peak areas: 3 : 2 : 1 : 3 : 2 : 1 : 2 (for equivalent protons)

BUT, for the 'end' =CH2 alkene protons, you can get two chemical shifts close together, if there are two different groups attached to the other carbon of the C=C bond i.e. R"R'C=CH2 where R" and R' are different. This causes the two =CH2 protons to experience slightly different fields.

 

(7) 5-methylhex-1-ene, alkenes structure and naming (c) doc b , alkenes structure and naming (c) doc b (5-methyl-1-hexene)

5-methylhex-1-ene 5-methyl-1-hexene structural skeletal formula isomer of C7H14 , skeletal formula

A branched alkene with no E/Z 'geometrical' or R/S 'optical' stereoisomers

Number of low resolution NMR chemical shift δ signal peaks: 6 1H and 6 13C (email if disagree?)

1H NMR ratio of integrated proton peak areas: 6 (3+3) : 1 : 2 : 2 : 1 : 2 (for equivalent protons)

BUT, for the 'end' =CH2 alkene protons, you can get two chemical shifts close together, if there are two different groups attached to the other carbon of the C=C bond i.e. R"R'C=CH2 where R" and R' are different. This causes the two =CH2 protons to experience slightly different fields.

 

(8) 2-methylhex-2-ene, alkenes structure and naming (c) doc b , alkenes structure and naming (c) doc b (2-methyl-2-hexene)

2-methylhex-2-ene 2-methyl-2-hexene structural skeletal formula isomer of C7H14 , skeletal formula

A branched alkene with no E/Z 'geometrical' or R/S 'optical' stereoisomers

Number of low resolution NMR chemical shift δ signal peaks: 5 1H and 6 13C (email if disagree?)

1H NMR ratio of integrated proton peak areas: 3 : 2 : 2 : 1 : 6 (3+3)  (for equivalent protons)

 

(9) 3-methylhex-2-ene, alkenes structure and naming (c) doc b , skeletal formula, 3-methyl-2-hexene

(E)-3-methylhex-2-ene, (E)-3-methyl-2-hexene, (Z)-3-methylhex-2-ene, (Z)-3-methyl-2-hexene structural skeletal formula isomer of C7H14

has two E/Z geometrical isomers: E- alkenes structure and naming (c) doc b and Z- alkenes structure and naming (c) doc b

From the CIP assignment priority rule for E/Z isomers: 6C6C  >  6C1H  >  1H

CIP rule for the four atoms/groups around the >C=C< double bond

(E)-3-methylhex-2-ene, (E)-3-methyl-2-hexene, (Z)-3-methylhex-2-ene, (Z)-3-methyl-2-hexene

Number of low resolution NMR chemical shift δ signal peaks: 6 1H and 7 13C (email if disagree?)

1H NMR ratio of integrated proton peak areas: 3 : 2 : 2 : 3 : 1 : 3 (for equivalent protons)

 

(10) 4-methylhex-2-ene, alkenes structure and naming (c) doc b , skeletal formula

(Z)-4-methylhex-2-ene, (Z)-4-methyl-2-hexene (E)-4-methylhex-2-ene, (E)-4-methyl-2-hexene structural skeletal formula isomer of C7H14

has two E/Z geometrical  isomers: Z/cis- alkenes structure and naming (c) doc b , (Z)-4-methylhex-2-ene, (Z)-4-methyl-2-hexene and E/trans- alkenes structure and naming (c) doc b , (E)-4-methylhex-2-ene, (E)-4-methyl-2-hexene

From the CIP assignment priority rule for E/Z isomers: 6C  >  1H

CIP rule for the four atoms/groups around the >C=C< double bond

both E/Z isomers can also theoretically exhibit R/S 'optical' isomerism, complicated - university level.

R/S stereoisomers as carbon atom C4 is chiral (asymmetric, stereocentre)

Number of low resolution NMR chemical shift δ signal peaks: 7 1H and 7 13C (email if disagree?)

1H NMR ratio of integrated proton peak areas: 3 : 2 : 1 : 3 : 1 : 1 : 3 (for equivalent protons)

 

(11) 5-methylhex-2-ene, alkenes structure and naming (c) doc b , skeletal formula

has two E/Z geometrical isomers: (E)-5-methylhex-2-ene, (E)-5-methyl-2-hexene, (Z)-5-methylhex-2-ene, (Z)-5-methyl-2-hexene structural skeletal formula isomer of C7H14

(E)-5-methylhex-2-ene, (E)-5-methyl-2-hexene, (Z)-5-methylhex-2-ene, (Z)-5-methyl-2-hexene

From the CIP assignment priority rule for E/Z isomers: 6C  >  1H

CIP rule for the four atoms/groups around the >C=C< double bond

Number of low resolution NMR chemical shift δ signal peaks: 6 1H and 6 13C (email if disagree?)

1H NMR ratio of integrated proton peak areas: 6 (3+3) : 1 : 2 : 1 : 1 : 3 (for equivalent protons)

Z/cis- alkenes structure and naming (c) doc b and E/trans- alkenes structure and naming (c) doc b

 

 

(12) 2-methylhex-3-ene, alkenes structure and naming (c) doc b , skeletal formula

has E/Z geometrical isomers: (E)-2-methylhex-3-ene, (E)-2-methyl-3-hexene, (Z)-2-methylhex-3-ene, (Z)-2-methyl-3-hexene structural skeletal formula isomer of C7H14

(E)-2-methylhex-3-ene, (E)-2-methyl-3-hexene, (Z)-2-methylhex-3-ene, (Z)-2-methyl-3-hexene

Z- alkenes structure and naming (c) doc b and E- alkenes structure and naming (c) doc b (cis and trans 2-methyl-3-hexene)

From the CIP assignment priority rule for E/Z isomers: 6C6C  >  6C1H  >  1H

CIP rule for the four atoms/groups around the >C=C< double bond

Number of low resolution NMR chemical shift δ signal peaks: 6 1H and 6 13C (email if disagree?)

1H NMR ratio of integrated proton peak areas: 3 : 2 : 1 : 1 : 1 : 6 (3+3) (for equivalent protons)

 

(13) 3-methylhex-3-ene, alkenes structure and naming (c) doc b , skeletal formula

has E/Z geometrical isomers: (E)-3-methylhex-3-ene, (E)-3-methyl-3-hexene, (Z)-3-methylhex-3-ene, (Z)-3-methyl-3-hexene structural skeletal formula isomer of C7H14

(E)-3-methylhex-3-ene, (E)-3-methyl-3-hexene, (Z)-3-methylhex-3-ene, (Z)-3-methyl-3-hexene

Z- alkenes structure and naming (c) doc b and E- alkenes structure and naming (c) doc b  (cis and trans 3-methyl-3-hexene)

From the CIP assignment priority rule for E/Z isomers: 6C6C  >  6C1H  >  1H

CIP rule for the four atoms/groups around the >C=C< double bond

Number of low resolution NMR chemical shift δ signal peaks: 6 1H and 7 13C (email if disagree?)

1H NMR ratio of integrated proton peak areas: 3 : 2 : 1 : 3 : 2 : 3 (for equivalent protons)

 

(14) 2,3-dimethypent-1-ene, 2,3-dimethypent-1-ene 2,3-dimethyl-1-pentene structural skeletal formula isomer of C7H14 , skeletal formula, 2,3-dimethyl-1-pentene

R/S 'optical' isomers (pair of enantiomers)

R/S stereoisomers as carbon atom C3 is chiral (asymmetric, stereocentre)

Number of low resolution NMR chemical shift δ signal peaks: 6 1H and 7 13C (email if disagree?)

1H NMR ratio of integrated proton peak areas: 3 : 2 : 1 : 3 : 3 : 2 (for equivalent protons)

BUT, for the 'end' =CH2 alkene protons, you can get two chemical shifts close together, if there are two different groups attached to the other carbon of the C=C bond i.e. R"R'C=CH2 where R" and R' are different. This causes the two =CH2 protons to experience slightly different fields.

 

(15) 2,4-dimethylpent-1-ene, 2,4-dimethylpent-1-ene 2,4-dimethyl-1-pentene structural skeletal formula isomer of C7H14 , skeletal formula, 2,4-dimethyl-1-pentene

A branched alkene with no E/Z 'geometrical' or R/S 'optical' stereoisomers

Number of low resolution NMR chemical shift δ signal peaks: 5 1H and 6 13C (email if disagree?)

1H NMR ratio of integrated proton peak areas: 6 (3+3) : 1 : 2 : 3 : 2 (for equivalent protons)

BUT, for the 'end' =CH2 alkene protons, you can get two chemical shifts close together, if there are two different groups attached to the other carbon of the C=C bond i.e. R"R'C=CH2 where R" and R' are different. This causes the two =CH2 protons to experience slightly different fields.

 

(16) 3,3-dimethylpent-1-ene, 3,3-dimethylpent-1-ene 3,3-dimethyl-1-pentene structural skeletal formula isomer of C7H14 , skeletal formula, 3,3-dimethyl-1-pentene

A branched alkene with no E/Z 'geometrical' or R/S 'optical' stereoisomers

Number of low resolution NMR chemical shift δ signal peaks: 5 1H and 6 13C (email if disagree?)

1H NMR ratio of integrated proton peak areas: 3 : 2 : 6 (3+3) : 1 : 2 (for equivalent protons)

BUT, for the 'end' =CH2 alkene protons, you can get two chemical shifts close together, if there are two different groups attached to the other carbon of the C=C bond i.e. R"R'C=CH2 where R" and R' are different. This causes the two =CH2 protons to experience slightly different fields.

 

(17) 3,4-dimethylpent-1-ene, 3,4-dimethylpent-1-ene 3,4-dimethyl-1-pentene structural skeletal formula isomer of C7H14 , skeletal formula, 3,4-dimethyl-1-pentene

A branched alkene with no E/Z 'geometrical' but has R/S 'optical' stereoisomers because C3 is chiral stereocentre.

Number of low resolution NMR chemical shift δ signal peaks: 6 1H and 6 13C (email if disagree?)

1H NMR ratio of integrated proton peak areas: 6 (3+3) : 1 : 1 : 3 : 1 : 2 (for equivalent protons)

BUT, for the 'end' =CH2 alkene protons, you can get two chemical shifts close together, if there are two different groups attached to the other carbon of the C=C bond i.e. R"R'C=CH2 where R" and R' are different. This causes the two =CH2 protons to experience slightly different fields.

 

(18) 4,4-dimethylpent-1-ene, 4,4-dimethylpent-1-ene 4,4-dimethyl-1-pentene structural skeletal formula isomer of C7H14 , skeletal formula, 4,4-dimethyl-1-pentene

A branched alkene with no E/Z 'geometrical' or R/S 'optical' stereoisomers

Number of low resolution NMR chemical shift δ signal peaks: 4 1H and 6 13C (email if disagree?)

1H NMR ratio of integrated proton peak areas: 9 (3x3) : 2 : 1 : 2 (for equivalent protons)

BUT, for the 'end' =CH2 alkene protons, you can get two chemical shifts close together, if there are two different groups attached to the other carbon of the C=C bond i.e. R"R'C=CH2 where R" and R' are different. This causes the two =CH2 protons to experience slightly different fields.

 

(19) 2-ethylpent-1-ene (3-methylenehexane), 2-ethylpent-1-ene (3-methylenepentane) 2-ethyl-1-pentene structural skeletal formula isomer of C7H14 , skeletal formula, 2-ethyl-1-pentene

A branched alkene with no E/Z 'geometrical' or R/S 'optical' stereoisomers

Number of low resolution NMR chemical shift δ signal peaks: 6 1H and 7 13C (email if disagree?)

1H NMR ratio of integrated proton peak areas: 3 : 2 : 2 : 2 : 3 : 2 (for equivalent protons)

BUT, for the 'end' =CH2 alkene protons, you can get two chemical shifts close together, if there are two different groups attached to the other carbon of the C=C bond i.e. R"R'C=CH2 where R" and R' are different. This causes the two =CH2 protons to experience slightly different fields.

 

(20) 3-ethylpent-1-ene, 2-ethylpent-1-ene (3-methylenepentane) 3-ethyl-1-pentene structural skeletal formula isomer of C7H14 , skeletal formula, 3-ethyl-1-pentene

A branched alkene with no E/Z 'geometrical' or R/S 'optical' stereoisomers

Number of low resolution NMR chemical shift δ signal peaks: 5 1H and 5 13C (email if disagree?)

1H NMR ratio of integrated proton peak areas: 6 (3+3) : 4 (2+2) : 1 : 1 : 2 (for equivalent protons)

BUT, for the 'end' =CH2 alkene protons, you can get two chemical shifts close together, if there are two different groups attached to the other carbon of the C=C bond i.e. R"R'C=CH2 where R" and R' are different. This causes the two =CH2 protons to experience slightly different fields.

 

(21) 2,3-dimethylpent-2-ene, 2,3-dimethylpent-2-ene 2,3-dimethy-2-pentene structural skeletal formula isomer of C7H14 , skeletal formula, 2,3-dimethy-2-pentene

A branched alkene with no E/Z 'geometrical' or R/S 'optical' stereoisomers

Number of low resolution NMR chemical shift δ signal peaks: 4 1H and 6 13C (email if disagree?)

1H NMR ratio of integrated proton peak areas: 3 : 2 : 3 : 6 (3+3) (for equivalent protons)

 

(22) 2,4-dimethylpent-2-ene, 2,4-dimethylpent-2-ene 2,4-dimethyl-2-pentene structural skeletal formula isomer of C7H14 , skeletal formula, 2,4-dimethyl-2-pentene

A branched alkene with no E/Z 'geometrical' or R/S 'optical' stereoisomers.

Like a number of the isomers, the two end methyl groups attached to C2 of the C=C bond, prohibit E/Z isomerism.

Number of low resolution NMR chemical shift δ signal peaks: 4 1H and 5 13C (email if disagree?)

1H NMR ratio of integrated proton peak areas: 6 (3+3) : 1 : 1 : 6 (3+3) (for equivalent protons)

 

(23) 3,4-dimethylpent-2-ene, 3,4-dimethylpent-2-ene 3,4-dimethyl-2-pentene structural skeletal formula isomer of C7H14 , 3,4-dimethyl-2-pentene

E/Z isomerism (pair of geometrical isomers)

skeletal formula of: (E)-3,4-dimethypent-2-ene, (E)-3,4-dimethyl-2-pentene, (Z)-3,4-dimethypent-2-ene, (Z)-3,4-dimethyl-2-pentene

From the CIP assignment priority rule for E/Z isomers: 6C6C  >  6C1H  >  1H

CIP rule for the four atoms/groups around the >C=C< double bond

Number of low resolution NMR chemical shift δ signal peaks: 5 1H and 6 13C (email if disagree?)

1H NMR ratio of integrated proton peak areas: 6 (3+3) : 1 : 3 : 1 : 3 (for equivalent protons)

 

(24) 4,4-dimethylpent-2-ene, (E)-4,4-dimethypent-2-ene, (E)-4,4-dimethyl-2-pentene, (Z)-4,4-dimethypent-2-ene, (Z)-4,4-dimethyl-2-pentene structural skeletal formula isomer of C7H14 , 4,4-dimethyl-2-pentene

E/Z isomerism (pair of geometrical isomers)

From the CIP assignment priority rule for E/Z isomers: 6C  >  1H

CIP rule for the four atoms/groups around the >C=C< double bond

Number of low resolution NMR chemical shift δ signal peaks: 4 1H and 5 13C (email if disagree?)

1H NMR ratio of integrated proton peak areas: 9 (3x3) : 1 : 1 : 3 (for equivalent protons)

skeletal formula of: (E)-4,4-dimethypent-2-ene, (E)-4,4-dimethyl-2-pentene, (Z)-4,4-dimethypent-2-ene, (Z)-4,4-dimethyl-2-pentene

 

(25) 2,3,3-trimethylbut-1-ene, 2,3,3-trimethylbut-1-ene 2,3,3-trimethyl-1-butene structural skeletal formula isomer of C7H14 , skeletal formula, 2,3,3-trimethyl-1-butene

A branched alkene with no E/Z 'geometrical' or R/S 'optical' stereoisomers

Number of low resolution NMR chemical shift δ signal peaks: 3 1H and 5 13C (email if disagree?)

1H NMR ratio of integrated proton peak areas: 9 (3x3) : 3 : 2 (for equivalent protons)

BUT, for the 'end' =CH2 alkene protons, you can get two chemical shifts close together, if there are two different groups attached to the other carbon of the C=C bond i.e. R"R'C=CH2 where R" and R' are different. This causes the two =CH2 protons to experience slightly different fields.


Secondly, saturated aliphatic cycloalkanes (alicyclic) compounds with a carbon ring of 3-7 carbon atoms

These are functional group isomers of the alkenes above.

Since these cycloalkanes have no C=C bond, none of these will show a characteristic, relatively strong and sharp absorption band in their infrared spectrum, around wavenumbers 1640-1680 cm-1 for the stretching vibration of the C=C bond.

(26) cycloheptane, cycloheptane structural skeletal formula isomer of C7H14 , skeletal formula

NO stereoisomerism i.e. no E/Z 'geometrical' isomers and no R/S 'optical' isomers (enantiomers).

A very symmetrical molecule.

Number of low resolution NMR chemical shift δ signal peaks: 1 1H and 1 13C (email if disagree?)

 

methylcyclohexane structural skeletal formula isomer of C7H14(27) methylcyclohexane, alkenes cycloalkane isomers of C7H14 structural formula methylcyclohexane, C7H14 alkanes molecular structure naming (c) doc b , methylcyclohexane, C7H14 skeletal formula alkanes molecular structure naming (c) doc b = !!! skeletal formula

NO stereoisomerism i.e. no E/Z 'geometrical' isomers and no R/S 'optical' isomers (enantiomers).

Number of low resolution NMR chemical shift δ signal peaks: 5 1H and 5 13C (email if disagree?)

1H NMR ratio of integrated proton peak areas: 2 : 4 (2+2) : 4 (2+2) : 1 : 3 (for equivalent protons)

 

ethylcyclopentane structural skeletal formula isomer of C7H14(28) ethylcyclopentane , alkenes cycloalkane isomers of C7H14 structural formula ethylcyclopentane, C7H14 alkanes molecular structure naming (c) doc b , ethylcyclopentane, C7H14 skeletal formula alkanes molecular structure naming (c) doc b , skeletal formula

NO stereoisomerism i.e. no E/Z 'geometrical' isomers and no R/S 'optical' isomers (enantiomers).

Number of low resolution NMR chemical shift δ signal peaks: 5 1H and 5 13C (email if disagree?)

1H NMR ratio of integrated proton peak areas: 4 (2+2) : 4 (2+2) : 1 : 2 : 3 (for equivalent protons)

 

1,1-dimethylcyclopentane structural skeletal formula isomer of C7H14(29) 1,1-dimethylcyclopentane , alkenes cycloalkane isomers of C7H14 structural formula 1,1-dimethylcyclopentane, C7H14 alkanes molecular structure naming (c) doc b , 1,1-dimethylcyclopentane, C7H14 skeletal formula alkanes molecular structure naming (c) doc b , skeletal formula

NO stereoisomerism i.e. no E/Z 'geometrical' isomers and no R/S 'optical' isomers (enantiomers).

Number of low resolution NMR chemical shift δ signal peaks: 3 1H and 4 13C (email if disagree?)

1H NMR ratio of integrated proton peak areas: 4 (2+2) : 4 (2+2) : 6 (3+3) (for equivalent protons)

 

1,2-dimethylcyclopentane structural skeletal formula isomer of C7H14(30) 1,2-dimethylcyclopentane , alkenes cycloalkane isomers of C7H14 structural formula 1,2-dimethylcyclopentane, C7H14 alkanes molecular structure naming (c) doc b , 1,2-dimethylcyclopentane, C7H14 skeletal formula alkanes molecular structure naming (c) doc b , skeletal formula

Theoretically E/Z and R/S isomers - complicated - university level

Number of low resolution NMR chemical shift δ signal peaks: 4 1H and 4 13C (email if disagree?)

1H NMR ratio of integrated proton peak areas: 2 : 4 (2+2) : 2 (1+1) : 6 (3+3) (for equivalent protons)

 

1,3-dimethylcyclopentane structural skeletal formula isomer of C7H14(31) 1,3-dimethylcyclopentane , alkenes cycloalkane isomers of C7H14 structural formula 1,3-dimethylcyclopentane, C7H14 alkanes molecular structure naming (c) doc b , 1,3-dimethylcyclopentane, C7H14 skeletal formula alkanes molecular structure naming (c) doc b , skeletal formula

E/Z and R/S isomers - complicated - university level

Number of low resolution NMR chemical shift δ signal peaks: 4 1H and 4 13C (email if disagree?)

1H NMR ratio of integrated proton peak areas: 4 (2+2) : 2 (1+1) : 2 : 6 (3+3) (for equivalent protons)

 

(32) propylcyclobutane, propylcyclobutane structural skeletal formula isomer of C7H14 , skeletal formula

NO stereoisomerism i.e. no E/Z 'geometrical' isomers and no R/S 'optical' isomers (enantiomers).

Number of low resolution NMR chemical shift δ signal peaks: 6 1H and 6 13C (email if disagree?)

1H NMR ratio of integrated proton peak areas: 2 : 4 (2+2) : 1 : 2 : 2 : 3 (for equivalent protons)

 

(33) isopropylcyclobutane, isopropylcyclobutane structural skeletal formula isomer of C7H14 , skeletal formula

NO stereoisomerism i.e. no E/Z 'geometrical' isomers and no R/S 'optical' isomers (enantiomers).

Number of low resolution NMR chemical shift δ signal peaks: 5 1H and 5 13C (email if disagree?)

1H NMR ratio of integrated proton peak areas: 2 : 4 (2+2) : 1 : 1 : 6 (3+3) (for equivalent protons)

 

(34) 1-ethyl-1-methylcyclobutane, 1-ethyl-1-methylcyclobutane structural skeletal formula isomer of C7H14 , skeletal formula

NO stereoisomerism i.e. no E/Z 'geometrical' isomers and no R/S 'optical' isomers (enantiomers).

Number of low resolution NMR chemical shift δ signal peaks: 5 1H and 6 13C (email if disagree?)

1H NMR ratio of integrated proton peak areas: 2 : 4 (2+2) : 3 : 2 : 3 (for equivalent protons)

 

(35) 1-ethyl-2-methylcyclobutane, 1-ethyl-2-methylcyclobutane structural skeletal formula isomer of C7H14 , skeletal formula

E/Z and R/S isomers possible - university level analysis.

Number of low resolution NMR chemical shift δ signal peaks: 7 1H and 7 13C (email if disagree?)

1H NMR ratio of integrated proton peak areas: 2 : 2 : 1 : 2 : 3  : 1 : 3 (for equivalent protons)

 

(36) 1-ethyl-3-methylcyclobutane, 1-ethyl-3-methylcyclobutane structural skeletal formula isomer of C7H14 , skeletal formula

E/Z geometrical isomers.

Number of low resolution NMR chemical shift δ signal peaks: 6 1H and 6 13C (email if disagree?)

1H NMR ratio of integrated proton peak areas: 3 : 1 : 4(2+2) : 1 : 2 : 3 (for equivalent protons)

 

(37) 1,1,2-trimethylcyclobutane, 1,1,2-trimethylcyclobutane structural skeletal formula isomer of C7H14 , skeletal formula

R/S isomerism possible, C2 is chiral.

Number of low resolution NMR chemical shift δ signal peaks: 5 1H and 6 13C (email if disagree?)

1H NMR ratio of integrated proton peak areas: 2 : 2 : 6 (3+3) : 1 : 3 (for equivalent protons)

 

(38) 1,1,3-trimethylcyclobutane, 1,1,3-trimethylcyclobutane structural skeletal formula isomer of C7H14 , skeletal formula

NO stereoisomerism i.e. no E/Z 'geometrical' isomers and no R/S 'optical' isomers (enantiomers).

Number of low resolution NMR chemical shift δ signal peaks: 4 1H and 5 13C (email if disagree?)

1H NMR ratio of integrated proton peak areas: 3 : 1 : 4 (2+2) : 6 (3+3) (for equivalent protons)

 

(39) 1,2,3-trimethylcyclobutane, 1,2,3-trimethylcyclobutane structural skeletal formula isomer of C7H14 , skeletal formula

'geometrical' E/Z and 'optical' R/S isomerism possible - complicated analysis - university level

Number of low resolution NMR chemical shift δ signal peaks: 7 1H and 7 13C (email if disagree?)

1H NMR ratio of integrated proton peak areas: 3 : 1 : 2 : 1 : 3 : 1 : 3 (for equivalent protons)

 

(40) butylcyclopropane, butylcyclopropane, 1-cyclopropylbutane structural skeletal formula isomer of C7H14 , skeletal formula

NO stereoisomerism i.e. no E/Z 'geometrical' isomers and no R/S 'optical' isomers (enantiomers).

Number of low resolution NMR chemical shift δ signal peaks: 6 1H and 6 13C (email if disagree?)

1H NMR ratio of integrated proton peak areas: 4 (2+2) : 1 : 2 : 2 : 2 : 3 (for equivalent protons)

 

(41) 2-cyclopropylbutane, 2-cyclopropylbutane structural skeletal formula isomer of C7H14 , skeletal formula

R/S 'optical' isomerism, carbon atom 2 of the butane chain is chiral.

Number of low resolution NMR chemical shift δ signal peaks: 6 1H and 6 13C (email if disagree?)

1H NMR ratio of integrated proton peak areas: 4 (2+2) : 1 : 1 : 3 : 2 : 3 (for equivalent protons)

 

(42) (2-methylpropyl)-cyclopropane, 1-cyclopropyl-2-methylpropane, (2-methylpropyl)-cyclopropane, 1-cyclopropyl-2-methylpropane structural skeletal formula isomer of C7H14 , skeletal formula

NO stereoisomerism i.e. no E/Z 'geometrical' isomers and no R/S 'optical' isomers (enantiomers).

Number of low resolution NMR chemical shift δ signal peaks: 5 1H and 5 13C (email if disagree?)

1H NMR ratio of integrated proton peak areas: 4 (2+2) : 1 : 2 : 1 : 6 (3+3) (for equivalent protons)

 

(43) 1-methyl-1-isopropylcyclobutane, 1-cyclopropyl-1-methylpropane, 1-methyl-1-isopropylcyclobutane, 1-cyclopropyl-1-methylpropane structural skeletal formula isomer of C7H14 , skeletal formula

NO stereoisomerism i.e. no E/Z 'geometrical' isomers and no R/S 'optical' isomers (enantiomers).

Number of low resolution NMR chemical shift δ signal peaks: 5 1H and 6 13C (email if disagree?)

1H NMR ratio of integrated proton peak areas: 4 (2+2) : 3 : 2 : 2 : 3 (for equivalent protons)

 

(44) 1-methyl-2-propylcyclopropane, 1-methyl-2-propylcyclopropane structural skeletal formula isomer of C7H14 , skeletal formula

'geometrical' E/Z and 'optical' R/S isomerism possible - complicated analysis - university level

Number of low resolution NMR chemical shift δ signal peaks: 7 1H and 7 13C (email if disagree?)

1H NMR ratio of integrated proton peak areas: 2 : 1 : 2 : 2 : 3 : 1 : 3 (for equivalent protons)

 

(45) 1-methyl-1-isopropylcyclopropane, 1-methyl-1-isopropylcyclopropane structural skeletal formula isomer of C7H14 , skeletal formula

NO stereoisomerism i.e. no E/Z 'geometrical' isomers and no R/S 'optical' isomers (enantiomers).

Number of low resolution NMR chemical shift δ signal peaks: 4 1H and 5 13C (email if disagree?)

1H NMR ratio of integrated proton peak areas: 4 (2+2) : 3 : 1 : 6 (3+3) (for equivalent protons)

 

(46) 1-methyl-2-isopropylcyclopropane, 1-methyl-2-isopropylcyclopropane structural skeletal formula isomer of C7H14 , skeletal formula

'geometrical' E/Z and 'optical' R/S isomerism possible - complicated analysis - university level

Number of low resolution NMR chemical shift δ signal peaks: 6 1H and 6 13C (email if disagree?)

1H NMR ratio of integrated proton peak areas: 2 : 1 : 1 : 6 (3+3) : 1 : 3 (for equivalent protons)

 

(47) 1,1-diethylcyclopropane, 1,1-diethylcyclopropane structural skeletal formula isomer of C7H14 , skeletal formula

NO stereoisomerism i.e. no E/Z 'geometrical' isomers and no R/S 'optical' isomers (enantiomers).

Number of low resolution NMR chemical shift δ signal peaks: 3 1H and 4 13C (email if disagree?)

1H NMR ratio of integrated proton peak areas: 4 (2+2) : 4 (2+2) : 6 (3+3) (for equivalent protons)

Reduced number of NMR peaks due to the very high symmetry of the molecule.

 

(48) 1,2-diethylcyclopropane, 1,2-diethylcyclopropane structural skeletal formula isomer of C7H14 , skeletal formula

'geometrical' E/Z and 'optical' R/S isomerism possible - complicated analysis - university level

Number of low resolution NMR chemical shift δ signal peaks: 4 1H and 4 13C (email if disagree?)

1H NMR ratio of integrated proton peak areas: 2 : 2 (1+1) : 4 (2+2) : 6 (3+3) (for equivalent protons)

Reduced number of NMR peaks due to the very high symmetry of the molecule.

 

(49) 1-ethyl-1,2-dimethylcyclopropane, 2-ethyl-1,2-dimethylcyclopropane, 1-ethyl-1,2-dimethylcyclopropane, 2-ethyl-1,2-dimethylcyclopropane structural skeletal formula isomer of C7H14 , skeletal formula

'geometrical' E/Z and 'optical' R/S isomerism possible - complicated analysis - university level

Number of low resolution NMR chemical shift δ signal peaks: 6 1H and 7 13C (email if disagree?)

1H NMR ratio of integrated proton peak areas: 2 : 3 : 2 : 3 : 1 : 3 (for equivalent protons)

 

(50) 2-ethyl-1,1-dimethylcyclopropane, 2-ethyl-1,1-dimethylcyclopropane structural skeletal formula isomer of C7H14 , skeletal formula

NO stereoisomerism i.e. no E/Z 'geometrical' isomers and no R/S 'optical' isomers (enantiomers).

Number of low resolution NMR chemical shift δ signal peaks: 5 1H and 6 13C (email if disagree?)

1H NMR ratio of integrated proton peak areas: 2 : 1 : 2 : 3 : 6 (3+3) (for equivalent protons)

 

(51) 1-ethyl-2,3-dimethylcyclopropane, 1-ethyl-2,3-dimethylcyclopropane structural skeletal formula isomer of C7H14 , skeletal formula

'geometrical' E/Z and 'optical' R/S isomerism possible - complicated analysis - university level

Number of low resolution NMR chemical shift δ signal peaks: 5 1H and 5 13C (email if disagree?)

1H NMR ratio of integrated proton peak areas: 6 (3+3) : 2 (1+1) : 1 : 2 : 3 (for equivalent protons)

 

(52) 1,1,2,2-tetramethylcyclopropane, 1,1,2,2-tetramethylcyclopropane structural skeletal formula isomer of C7H14 , skeletal formula

Number of low resolution NMR chemical shift δ signal peaks: 2 1H and 3 13C (email if disagree?)

1H NMR ratio of integrated proton peak areas: 2 : 12 (4x3) = 1 : 6 (for equivalent protons)

NO stereoisomerism i.e. no E/Z 'geometrical' isomers and no R/S 'optical' isomers (enantiomers).

Reduced number of NMR peaks due to the very high symmetry of the molecule.

 

(53) 1,1,2,3-tetramethylcyclopropane, 1,1,2,3-tetramethylcyclopropane structural skeletal formula isomer of C7H14 , skeletal formula

'geometrical' E/Z and 'optical' R/S isomerism possible - complicated analysis - university level

Number of low resolution NMR chemical shift δ signal peaks: 3 1H and 4 13C (email if disagree?)

1H NMR ratio of integrated proton peak areas: 6 (3+3) : 2 (1+1) : 6 (3+3) = 2 : 1 : 3 (for equivalent protons)

Reduced number of NMR peaks due to the very high symmetry of the molecule.


(C) EXTRA NOTES selected isomers of C7H14

There are many constitutional isomers of C7H14, including straight-chain and branched alkenes, as well as cycloalkanes.

These exhibit chain, position, and functional group isomerism, with distinct physical and chemical properties, reactivities, and applications.


Constitutional Isomers of C7H14

C7H14 has one degree of unsaturation, allowing for either:

  • Alkenes (with one C=C double bond)

  • Cycloalkanes (with one ring, can only have one!)

Straight and Branched Alkenes (Acyclic)

Isomer Type

Example Name

Description

Straight-chain alkene

1-heptene, 2-heptene

Double bond at different positions

Branched alkene

2-methylhexene, 3-methylhexene

Methyl branch with varying C=C position

Geometric isomers

cis-/trans-2-heptene

Restricted rotation around C=C

Cycloalkanes

Isomer Type

Example Name

Description

Cycloheptane

Unbranched ring

Saturated ring

Methylcyclohexane

One methyl substituent

Position affects isomer type

Ethylcyclopentane

Five-membered ring + ethyl

Ring size variation


Types of Isomerism Exhibited by the isomers of C7H14

  • Chain Isomerism: Different carbon skeletons (e.g., straight vs. branched).

  • Position Isomerism: Location of double bond or substituent varies.

  • Functional Group Isomerism: Alkenes vs. cycloalkanes.

  • Geometric (cis-trans) Isomerism: In alkenes with restricted rotation around C=C.


Differences in Physical Properties of the isomers of C7H14

Property

Alkenes

Cycloalkanes

Boiling Point

Slightly lower

Slightly higher

Density

Lower

Higher

Reactivity

More reactive (C=C)

Less reactive

Solubility in water

Insoluble

Insoluble


Differences in Chemical Reactions and Reactivity of isomers of C7H14

  • Alkenes:

    • Undergo electrophilic addition (e.g., bromination, hydration).

    • Can form polymers (e.g., polyethylene from ethene).

    • React with KMnO4 (oxidation) and HBr (Markovnikov/anti-Markovnikov).

  • Cycloalkanes:

    • Undergo substitution reactions.

    • Less reactive than alkenes due to lack of π-bond.

    • Can undergo ring-opening under specific conditions.

Relative Reactivity:
Alkenes > Cycloalkanes
(π-bond in alkenes makes them more reactive toward electrophiles.)


Uses and Applications of isomers of C7H14

  • Alkenes: Precursors to plastics, alcohols, and industrial chemicals.

  • Cycloalkanes: Used in fuel additives, solvents, and synthetic intermediates.


Common Student Misconceptions about isomers of C7H14

  • Confusing chain isomerism with position isomerism.

  • Forgetting cis-trans isomerism applies only to alkenes with two different groups on each C of the double bond.

  • Assuming cycloalkanes are aromatic—they are not.

  • Believing all isomers have similar boiling points—branching lowers boiling point.


Exam Revision Tips for questions that may involve isomers of C7H14

  • Draw all isomers: Use skeletal structures to visualize chain and ring variations.

  • Practice IUPAC naming: Focus on longest chain, position of double bond, and substituents.

  • Use reaction maps: Compare addition reactions of alkenes vs. substitution in cycloalkanes.

  • For spectroscopy:

    • ¹H NMR: Alkenes show downfield signals (~5–6 ppm); cycloalkanes ~1–2 ppm.

    • IR: Alkenes show C=C stretch (~1640 cm⁻¹); cycloalkanes lack this.

  • Model kits: Help visualize cis-trans isomerism and ring strain.

  • Past papers: Focus on isomer identification, naming, and reaction mechanisms.


(D) Learning objectives - questions to be answered?

Can you IUPAC name these C7H14 isomers?

Can you deduce the number of principal 1H chemical shifts and proton ratio you would expect to see in the NMR spectrum of these C7H14 isomers?

Can you deduce the number of principal 13C chemical shifts you would expect to see in the NMR spectrum of these C7H14 isomers?

How many isomers are there of molecular formula C7H14?

How do you work out the structure of the isomers of molecular formula C7H14?

How do you draw the constitutional-structural formula of the isomers of molecular formula C7H14?

How do you draw the skeletal formula of the isomers of molecular formula C7H14?

How do you name the isomers of molecular formula C7H14?

How many aliphatic structural isomers are there of molecular formula C7H14?

How many aliphatic carbon chain isomers are there of molecular formula C7H14?

How many positional isomers are there of molecular formula C7H14?

Does C7H14 have any stereoisomers?

Are there any E/Z (geometrical) or RS (optical) stereoisomers (enantiomers) of C7H14?

Are there any aliphatic open chain alkene isomers of molecular formula C7H14?

Are there any alkane/cycloalkane isomers of molecular formula C7H14?

Are there any alkene/cycloalkene/diene/alkyne isomers of molecular formula C7H14?

Are there any alicyclic cycloalkane isomers of molecular formula C7H14?

Are there any functional group isomers with a molecular formula C7H14?

This page will answer these questions for molecular formula C7H14


(E) QUESTIONS

Practise exam questions based on isomers of molecular formula the isomers of C7H14

Jot down your responses with explanations.

 ANSWERS to the questions based on the isomers of C7H14

If you think there are any errors, please email me asap at chem55555@hotmail.com

I don't mind if students/teachers do a selected printout of these questions and answers.


Given these six selected isomers of molecular formula C7H14 ....

A isomers of C7H14 heptene alkenes structure and naming (c) doc b B (c) doc b C 3,4-dimethylpent-1-ene 3,4-dimethyl-1-pentene structural skeletal formula isomer of C7H14
D 1,2-dimethylcyclopentane structural skeletal formula isomer of C7H14 E 2,4-dimethylpent-2-ene 2,4-dimethyl-2-pentene structural skeletal formula isomer of C7H14 F 1,1,2,3-tetramethylcyclopropane structural skeletal formula isomer of C7H14

Q1 Name as many of isomers A to F as you can with a correct IUPAC name.


Q2 (a) Which of A, B, C and E is an E/Z (geometrical) isomer of C7H14?

(b) is it the E or Z isomer?

(c) Why can't E be an E/Z isomer?


Q3 Which of A, B, C and E is an R/S (optical) isomer of C7H14?


Q4 Which of these C7H14 isomers will not readily react with bromine in an organic solvent at room temperature?


Q5 In its NMR spectra, which C7H14 isomer will display four 1H and four 13C chemical shifts?


Q6 In its NMR spectra, which C7H14 isomer  will display three 1H and four 13C chemical shifts?


Q7 What would the most significant difference in the infrared spectra of A, B, C and E compared to D and F?

A isomers of C7H14 heptene alkenes structure and naming (c) doc b B (c) doc b C 3,4-dimethylpent-1-ene 3,4-dimethyl-1-pentene structural skeletal formula isomer of C7H14
D 1,2-dimethylcyclopentane structural skeletal formula isomer of C7H14 E 2,4-dimethylpent-2-ene 2,4-dimethyl-2-pentene structural skeletal formula isomer of C7H14 F 1,1,2,3-tetramethylcyclopropane structural skeletal formula isomer of C7H14

Jot down your responses with explanations.

 ANSWERS to the questions based on the isomers of C7H14

If you think there are any errors, please email me asap at chem55555@hotmail.com

I don't mind if students/teachers do a selected printout of these questions and answers.


Associated organic chemistry  links

 Advanced Level pre-university organic chemistry notes

 IR, mass and H-1 & C-13 NMR spectra of organic compounds

See also Examples of the effects of isomerism on the similarity or difference in the physical and chemical properties of structural isomers

and Examples of comparing the physical and chemical properties of alkene E/Z isomers

Index of sets of isomers for a given molecular formula

The molecular structure and naming of ALKANES

The molecular structure and naming of ALKENES

Index of revision notes on the chemistry of ALKANES and the petrochemical industry

INDEX of ALL revision notes on the chemistry ALKENES including reactions and polymers

Isomerism: introduction, structural isomerism - chain, positional, functional group, tautomerism

Stereoisomerism: introduction, definition, priority rules, E/Z isomerism (cis/trans isomerism)

Stereoisomerism - R/S isomerism (optical isomerism) - definition - examples explained

 This is a big chemistry website, please allow time to explore it

Index of my advanced (pre-college/university) organic chemistry revision notes

 Index of all my spectroscopy pages

 Index of all my isomerism pages

 The chemistry of alkanes and the petrochemical industry

 The chemistry of alkenes

 The chemistry of haloalkanes

 The chemistry of alcohols

 The chemistry of aldehydes and ketones

 The chemistry of carboxylic acids and derivatives

 The chemistry of organo-nitrogen compounds

 The chemistry of aromatic compounds

index for all isomerism pages

Website content © Dr Phil Brown 2000+. All copyrights reserved on revision notes, images, quizzes, worksheets etc. Copying of Doc Brown's pre-university advanced level chemistry website material is NOT permitted. Exam revision summaries & references to science course specifications are unofficial. These organic chemistry revision notes on isomerism are suitable for use of pre-university students studying AQA advanced level chemistry, Edexcel advanced level chemistry, OCR advanced level chemistry, IB advanced level chemistry, WJEC (Eduqas) advanced level chemistry, CIE advanced level chemistry, US grade 11-12 AP honors chemistry courses and they will also prove useful to 1st year undergraduate students of chemistry. The isomerism of molecules of formulae C7H14, structural constitutional isomers, E/Z geometrical isomers and R/S optical stereoisomers

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ANSWERS

Practise exam questions based on isomers of molecular formula the isomers of C7H14

If you think there are any errors, please email me asap at chem55555@hotmail.com

I don't mind if students/teachers do a selected printout of these questions and answers.


Given these six selected isomers of molecular formula C7H14 ....

A isomers of C7H14 heptene alkenes structure and naming (c) doc b B (c) doc b C 3,4-dimethylpent-1-ene 3,4-dimethyl-1-pentene structural skeletal formula isomer of C7H14
D 1,2-dimethylcyclopentane structural skeletal formula isomer of C7H14 E 2,4-dimethylpent-2-ene 2,4-dimethyl-2-pentene structural skeletal formula isomer of C7H14 F 1,1,2,3-tetramethylcyclopropane structural skeletal formula isomer of C7H14

Q1 Name as many of isomers A to F as you can with a correct IUPAC name.

ANSWERS

A hept-1-ene,    B hept-2-ene,   C 3,4-dimethylpent-1-ene

D 1,2-dimethylcyclopentane,   E 2,4-dimethylpent-2-ene,   F 1,1,2,3-trimethylcyclopropane


Q2 (a) Which of A, B, C and E is an E/Z (geometrical) isomer of C7H14?

(b) is it the E or Z isomer?

(c) Why can't E be an E/Z isomer?

ANSWERS

(a) The B isomer because of the asymmetry at both ends of the C=C bond.

(b) It is the E isomer of hept-2ene, from the Cahn, Ingold and Prolog priority rule, the longer alkyl chain is > CH3 > H about the C=C bond.

(Z)-hept-2-ene, (Z)-2-heptene (E)-hept-2-ene. (E)-2-heptene structural skeletal formula isomer of C7H14

(c) The symmetry of two methyl groups on the right-hand end of the C=C bond.

Note: The alicyclic C7H14 isomers D and F exhibit an overlap of E/Z and R/S isomerism, but can you see why? (university level analysis needed here!)


Q3 Which of A, B, C and E is an R/S (optical) isomer of C7H14?

ANSWER: Isomer C, C3 is chiral, asymmetric, four different atoms/groups attached to the same carbon atom, therefore non-superimposable mirror images are possible (enantiomers).

Again, note: The alicyclic C7H14 isomers D and F exhibit a complex overlap of E/Z and R/S isomerism.


Q4 Which of these C7H14 isomers will not readily react with bromine in an organic solvent at room temperature?

ANSWER: D and F, they have no reactive C=C bond.


Q5 In its NMR spectra, which C7H14 isomer will display four 1H and four 13C chemical shifts?

ANSWER: isomer D, symmetrical molecule


Q6 In its NMR spectra, which C7H14 isomer  will display three 1H and four 13C chemical shifts?

ANSWER: isomer F, symmetrical molecule, but one less 1H peak because the C1 of the cyclopropane ring has no proton attached to it.


Q7 What would the most significant difference in the infrared spectra of A, B, C and E compared to D and F?

ANSWER: D and F would not show the prominent absorption band at ~1650 cm-1 due to the presence of a C=C group in the molecule.


A isomers of C7H14 heptene alkenes structure and naming (c) doc b B (c) doc b C 3,4-dimethylpent-1-ene 3,4-dimethyl-1-pentene structural skeletal formula isomer of C7H14
D 1,2-dimethylcyclopentane structural skeletal formula isomer of C7H14 E 2,4-dimethylpent-2-ene 2,4-dimethyl-2-pentene structural skeletal formula isomer of C7H14 F 1,1,2,3-tetramethylcyclopropane structural skeletal formula isomer of C7H14

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