How could IR spectroscopy be used to distinguish between the following compounds?

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter20: Dienes, Conjugated Systems, And Pericyclic Reactions
Section20.3: Uv-visible Spectroscopy
Problem 20.5P
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How could IR spectroscopy be used to distinguish between the following compounds?

a ketone and an aldehyde
An aldehyde would show absorption bands at 2820 – 2720 cm¬1. A ketone would not have these absorption bands.
O A ketone would show absorption bands at 1250 – 1050 cm-1. An aldehyde would not have these absorption bands.
O A ketone would show absorption bands at 3300 – 2500 cm-1. An aldehyde would not have these absorption bands.
An aldehyde would show absorption bands at 1780 – 1650 cm-1. A ketone would not have these absorption bands.
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Part B
a cyclic ketone and an open-chain ketone
O An open-chain ketone would have a methyl substituent and therefore an absorption band at 1385 – 1365 cm¬1 that a cyclic ketone would not have.
An open-chain ketone would have a methyl substituent and therefore an absorption band at 1650 – 1550 cm-1 that a cyclic ketone would not have.
An open-chain ketone would have a methyl substituent and therefore an absorption band at 2960 – 2850 cm-1 that a cyclic ketone would not have.
An open-chain ketone would have a methyl substituent and therefore an absorption band at 3300 – 2700 cm-1 that a cyclic ketone would not have.
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Transcribed Image Text:a ketone and an aldehyde An aldehyde would show absorption bands at 2820 – 2720 cm¬1. A ketone would not have these absorption bands. O A ketone would show absorption bands at 1250 – 1050 cm-1. An aldehyde would not have these absorption bands. O A ketone would show absorption bands at 3300 – 2500 cm-1. An aldehyde would not have these absorption bands. An aldehyde would show absorption bands at 1780 – 1650 cm-1. A ketone would not have these absorption bands. Submit Request Answer Part B a cyclic ketone and an open-chain ketone O An open-chain ketone would have a methyl substituent and therefore an absorption band at 1385 – 1365 cm¬1 that a cyclic ketone would not have. An open-chain ketone would have a methyl substituent and therefore an absorption band at 1650 – 1550 cm-1 that a cyclic ketone would not have. An open-chain ketone would have a methyl substituent and therefore an absorption band at 2960 – 2850 cm-1 that a cyclic ketone would not have. An open-chain ketone would have a methyl substituent and therefore an absorption band at 3300 – 2700 cm-1 that a cyclic ketone would not have. Submit Requert Angwor
benzene and cyclohexene
Benzene would show an sp3 C - H stretch slightly to the right of 2500 cm-1. Cyclohexene would not show an absorption band in this region.
Cyclohexene would show an sp C– H stretch slightly to the right of 2500 cm-1. Benzene would not show an absorption band in this region.
Benzene would show an sp3 C –H stretch slightly to the right of 3000 cm-1. Cyclohexene would not show an absorption band in this region.
O Cyclohexene would show an sp3 C- H stretch slightly to the right of 3000 cm-1. Benzene would not show an absorption band in this region.
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Part D
cis -2-hexene and trans-2-hexene
The cis isomer would show a carbon-hydrogen bending vibration at 960 –980 cm¬1, whereas the trans isomer would show a carbon-hydrogen bending vibration at
730 – 675 cm=1.
The cis isomer would show a carbon-hydrogen bending vibration at 990 – 910 cm¬1, whereas the trans isomer would show a carbon-hydrogen bending vibration at
890 cm-1.
The cis isomer would show a carbon-hydrogen bending vibration at 730 – 675 cm-1, whereas the trans isomer would show a carbon-hydrogen bending vibration at
960 – 980 cm¬1.
The cis isomer would show a carbon-hydrogen bending vibration at 840 – 800 cm, whereas the trans isomer would show a carbon-hydrogen bending vibration at
890 cm-1.
Transcribed Image Text:benzene and cyclohexene Benzene would show an sp3 C - H stretch slightly to the right of 2500 cm-1. Cyclohexene would not show an absorption band in this region. Cyclohexene would show an sp C– H stretch slightly to the right of 2500 cm-1. Benzene would not show an absorption band in this region. Benzene would show an sp3 C –H stretch slightly to the right of 3000 cm-1. Cyclohexene would not show an absorption band in this region. O Cyclohexene would show an sp3 C- H stretch slightly to the right of 3000 cm-1. Benzene would not show an absorption band in this region. Submit Request Answer Part D cis -2-hexene and trans-2-hexene The cis isomer would show a carbon-hydrogen bending vibration at 960 –980 cm¬1, whereas the trans isomer would show a carbon-hydrogen bending vibration at 730 – 675 cm=1. The cis isomer would show a carbon-hydrogen bending vibration at 990 – 910 cm¬1, whereas the trans isomer would show a carbon-hydrogen bending vibration at 890 cm-1. The cis isomer would show a carbon-hydrogen bending vibration at 730 – 675 cm-1, whereas the trans isomer would show a carbon-hydrogen bending vibration at 960 – 980 cm¬1. The cis isomer would show a carbon-hydrogen bending vibration at 840 – 800 cm, whereas the trans isomer would show a carbon-hydrogen bending vibration at 890 cm-1.
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