isolated from plants and have distinct aromas. For example, a -terpineol is a common perfume ingredient and smells similar to lilacs. HO a-terpineol B-terpineol y-terpineol 4-terpineol A) How many of each of the different types of carbon are present in 4-terpineol. Do not consider carbons attached to heteroatoms. or participating in pi bonds. i. Primary ii. Secondary iii. Tertiary iv. Quaternary B) Terpineols contain tertiary alcohols. While quaternary carbons exist, quaternary alcohols do not. Explain why a quaternary alcohol is not feasible. C) Is it necessary to use E/Z designations for any of these molecules? If so, provide the proper designation for each relevant molecule. If not, briefly explain why it isn't needed.

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Chapter1: Chemical Foundations
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2. The molecules shown below are four terpineol isomers. They are
isolated from plants and have distinct aromas. For example, a -terpineol
is a common perfume ingredient and smells similar to lilacs.
HO
a-terpineol
ß-terpineol
y-terpineol
4-terpineol
A) How many of each of the different types of carbon are present in 4-terpineol. Do not consider carbons attached to heteroatoms or
participating in pi bonds.
i. Primary
ii. Secondary
iii. Tertiary
iv. Quaternary
B) Terpineols contain tertiary alcohols. While quaternary carbons exist, quaternary alcohols do not. Explain why a quaternary
alcohol is not feasible.
C) Is it necessary to use E/Z designations for any of these molecules? If so, provide the proper designation for each relevant molecule.
If not, briefly explain why it isn't needed.
e. Draw a structural isomer of terpineol that meet the following criteria. You should draw one unique structure for each set. You
must draw each molecule twice, once as a skeletal structure and once as a complete Lewis structure showing all atoms, bonds,
and lone pairs of electrons.
i. Does not have a ring.
ii. Has an E alkene.
iii. Has a secondary alcohol.
iv. Does not contain an alcohol.
f. Draw a complete Lewis structure of a-terpineol, showing all bonds, atoms and lone pairs of electrons.
Transcribed Image Text:2. The molecules shown below are four terpineol isomers. They are isolated from plants and have distinct aromas. For example, a -terpineol is a common perfume ingredient and smells similar to lilacs. HO a-terpineol ß-terpineol y-terpineol 4-terpineol A) How many of each of the different types of carbon are present in 4-terpineol. Do not consider carbons attached to heteroatoms or participating in pi bonds. i. Primary ii. Secondary iii. Tertiary iv. Quaternary B) Terpineols contain tertiary alcohols. While quaternary carbons exist, quaternary alcohols do not. Explain why a quaternary alcohol is not feasible. C) Is it necessary to use E/Z designations for any of these molecules? If so, provide the proper designation for each relevant molecule. If not, briefly explain why it isn't needed. e. Draw a structural isomer of terpineol that meet the following criteria. You should draw one unique structure for each set. You must draw each molecule twice, once as a skeletal structure and once as a complete Lewis structure showing all atoms, bonds, and lone pairs of electrons. i. Does not have a ring. ii. Has an E alkene. iii. Has a secondary alcohol. iv. Does not contain an alcohol. f. Draw a complete Lewis structure of a-terpineol, showing all bonds, atoms and lone pairs of electrons.
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