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Published on: 27/05/2021
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Questions + Answers key
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1.
Explain why alkyl groups act as electron donors when attached to a π system.
2.
Consider structure I to VII and answer the following questions (i) and (ii).
I. \({ CH }_{ 3 }-{ CH }_{ 2 }-{ CH }_{ 2 }-{ CH }_{ 2 }-{ OH }\)
II.
\({ CH }_{ 3 }-{ CH }_{ 2 }-{ CH }-{ CH }_{ 3 }\\ \quad \quad \quad \quad \quad \quad \quad |\\ \quad \quad \quad \quad \quad \quad \quad { OH }\)
III.
\({ \quad \quad \quad \quad CH }_{ 3 }\\ \quad \quad \quad \quad |\\ { { CH }_{ 3 } }-{ C }-{ CH }_{ 3 }\\ \quad \quad \quad \quad |\\ \quad \quad \quad \quad { OH }\)
IV.
\({ CH }_{ 3 }-{ CH }-{ CH_{ 2 } }-{ OH }\\ \quad \quad \quad \quad |\\ \quad \quad \quad \quad { CH }_{ 3 }\)
V. \({ CH }_{ 2 }-{ CH }_{ 2 }-{ O }-{ CH }_{ 2 }-{ CH }_{ 3 }\)
VI.
\({ CH }_{ 2 }-{ O }-{ CH }_{ 2 }-{ CH }_{ 2 }-{ CH }_{ 3 }\)
VII.
\({ CH }_{ 3 }-{ O }-{ CH }-{ CH }_{ 3 }\\ \quad \quad \quad \quad \quad \quad |\\ \quad \quad \quad \quad \quad \quad { CH }_{ 3 }\)
Identify the pairs of compounds that represent chain isomerism.
3.
Consider structure I to VII and answer the following questions (i) and (ii).
I. \({ CH }_{ 3 }-{ CH }_{ 2 }-{ CH }_{ 2 }-{ CH }_{ 2 }-{ OH }\)
II. \({ CH }_{ 3 }-{ CH }_{ 2 }-{ CH }-{ CH }_{ 3 }\\ \quad \quad \quad \quad \quad \quad \quad |\\ \quad \quad \quad \quad \quad \quad \quad { OH }\)
III. \({ \quad \quad \quad \quad CH }_{ 3 }\\ \quad \quad \quad \quad |\\ { { CH }_{ 3 } }-{ C }-{ CH }_{ 3 }\\ \quad \quad \quad \quad |\\ \quad \quad \quad \quad { OH }\)
IV. \({ CH }_{ 3 }-{ CH }-{ CH_{ 2 } }-{ OH }\\ \quad \quad \quad \quad |\\ \quad \quad \quad \quad { CH }_{ 3 }\)
V. \({ CH }_{ 2 }-{ CH }_{ 2 }-{ O }-{ CH }_{ 2 }-{ CH }_{ 3 }\)
VI. \({ CH }_{ 2 }-{ O }-{ CH }_{ 2 }-{ CH }_{ 2 }-{ CH }_{ 3 }\)
VII. \({ CH }_{ 3 }-{ O }-{ CH }-{ CH }_{ 3 }\\ \quad \quad \quad \quad \quad \quad |\\ \quad \quad \quad \quad \quad \quad { CH }_{ 3 }\)
Identify the pairs of compounds that represent position isomerism.
4.
Consider structure I to VII and answer the following questions (i) and (ii).
I. \({ CH }_{ 3 }-{ CH }_{ 2 }-{ CH }_{ 2 }-{ CH }_{ 2 }-{ OH }\)
II. \({ CH }_{ 3 }-{ CH }_{ 2 }-{ CH }-{ CH }_{ 3 }\\ \quad \quad \quad \quad \quad \quad \quad |\\ \quad \quad \quad \quad \quad \quad \quad { OH }\)
III. \({ \quad \quad \quad \quad CH }_{ 3 }\\ \quad \quad \quad \quad |\\ { { CH }_{ 3 } }-{ C }-{ CH }_{ 3 }\\ \quad \quad \quad \quad |\\ \quad \quad \quad \quad { OH }\)
IV. \({ CH }_{ 3 }-{ CH }-{ CH_{ 2 } }-{ OH }\\ \quad \quad \quad \quad |\\ \quad \quad \quad \quad { CH }_{ 3 }\)
V. \({ CH }_{ 2 }-{ CH }_{ 2 }-{ O }-{ CH }_{ 2 }-{ CH }_{ 3 }\)
VI. \({ CH }_{ 2 }-{ O }-{ CH }_{ 2 }-{ CH }_{ 2 }-{ CH }_{ 3 }\)
VII. \({ CH }_{ 3 }-{ O }-{ CH }-{ CH }_{ 3 }\\ \quad \quad \quad \quad \quad \quad |\\ \quad \quad \quad \quad \quad \quad { CH }_{ 3 }\)
Identify the pairs of compound which are functional group isomers.
5.
Consider structure I to VII and answer the following questions (i) and (ii).
I. \({ CH }_{ 3 }-{ CH }_{ 2 }-{ CH }_{ 2 }-{ CH }_{ 2 }-{ OH }\)
II. \({ CH }_{ 3 }-{ CH }_{ 2 }-{ CH }-{ CH }_{ 3 }\\ \quad \quad \quad \quad \quad \quad \quad |\\ \quad \quad \quad \quad \quad \quad \quad { OH }\)
III. \({ \quad \quad \quad \quad CH }_{ 3 }\\ \quad \quad \quad \quad |\\ { { CH }_{ 3 } }-{ C }-{ CH }_{ 3 }\\ \quad \quad \quad \quad |\\ \quad \quad \quad \quad { OH }\)
IV. \({ CH }_{ 3 }-{ CH }-{ CH_{ 2 } }-{ OH }\\ \quad \quad \quad \quad |\\ \quad \quad \quad \quad { CH }_{ 3 }\)
V. \({ CH }_{ 2 }-{ CH }_{ 2 }-{ O }-{ CH }_{ 2 }-{ CH }_{ 3 }\)
VI. \({ CH }_{ 2 }-{ O }-{ CH }_{ 2 }-{ CH }_{ 2 }-{ CH }_{ 3 }\)
VII. \({ CH }_{ 3 }-{ O }-{ CH }-{ CH }_{ 3 }\\ \quad \quad \quad \quad \quad \quad |\\ \quad \quad \quad \quad \quad \quad { CH }_{ 3 }\)
(i) Which of the above compounds form pairs of metamers?
(ii) Identify the pairs of compounds which are functional group isomers.
(iii) Identify the pairs of compounds that represent position isomerism.
(iv) Identify the pairs of compounds that represent chain isomerism.
1.
Due to hyperconjugation, alkyl groups act as electron donors when attached to a \(\pi\)-system as shown below:
2.
I and III, I and IV, II and III and II and IV represent chain isomerism.
a) \({ CH }_{ 3 }CO{ CH }_{ 3 }\)
b) \(H-CH={ CH }_{ 2 }\).
3.
I and II, III and IV and, VI and VII represent position isomerism.
4.
I and V, I and VI, I and VII; II and V, II and VI, II and VII; III and V, II and VI; III and VI; III and VII; IV and V; IV and VI and IV and VII are functional group of isomers.
5.
(i) V and VI or VI and VII form a pair of metamers since they differ in the number of carbon atoms on the either side of the functional group, i.e. O-atom.
(ii) I and V, I and VI , I and VII; II and V, II and VI, II and VII ; III and V, II and VI; III and VII;IV and V ; IV and VI and IV and VII are all functional group isomers.
(iii) I and II, III and IV and, VI and VII represent position isomerism.
(iv) I and III, I and IV, II and III and II and IV represent chain isomerism.
(a) CH3COH3, (b) H - CH = CH2
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