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1.4 alcohols, ethers, thiols SV

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Alcohols, Ethers, Thiols

Alcohols

- contain the –OH functional group (hydroxyl)

R- OH where R is any alkyl group

- can be primary, secondary or tertiary, depending on the position of the hydroxyl group

- look at the C that the –OH is bonded to and count how many C’s is that C bonded to?

How to name an alcohol:

- locate the longest chain that contains the –OH group and number the chain so that the hydroxyl has the lowest
possible position number

- replace ending of parent chain to – ol

- add a position number before the –ol ending

- if there is more than one –OH leave the e in the alkane’s name and add di, tri, tetra etc, before the –ol

ex methanol -in antifreeze, causes blindness

ethanol -in alcoholic beverages

-commonly called ethyl alcohol

propan-2-ol -rubbing alcohol

-commonly called isopropanol

ethan-1,2-diol -commonly called ethylene glycol

Examples: -main component of antifreeze

OH

CH3-OH CH3-CH-CH3
HO-CH2-CH2-OH CH3-CH=CH-CHCH3

OH

Aromatic Alcohols …

Properties of Alcohols:

 Because alcohols have an OH group, they can form hydrogen bonds with other molecules. This leads
to:

 high boiling points than comparable alkanes

 greater solubility in water than comparable alkanes

 Polar OH group, and non-polar hydrocarbon chain

 Alcohols can be burned like hydrocarbons to produce water and carbon dioxide.

Ethers

- compounds that contain an oxygen attached to two carbons as the functional group

R- O – R’

- ethers are named as alkoxy derivatives of alkanes

- the –O-R group is the alkoxy group that may have names such as methoxy (-O-CH3), ethoxy (- O-CH2CH3) etc.

-the longer alkyl group is considered the parent chain, the shorter chain is the alkoxy group

- used to be named using the word ether following the combination of the two alkyl groups
CH3–O–CH2CH2CH3

CH3CH2–O–CHCH3

CH

CH3CH2–O–CH2CH3

O–CH3

CH3CH2CH2CHCHCH3

CH3

Properties of Ethers:

Like alkanes, ethers are very unreactive substances. Pure ethers cannot form hydrogen bonds and have lower boiling
points than similar alcohols. Ethers are used as anaesthetics.

Ethers are formed from the dehydration of alcohols, giving off water: Condensation Reaction

 Ethers have no OH group, so they cannot form hydrogen bonds. However, the C-O bond is still a polar bond,
making ethers more polar than hydrocarbons.

This leads to:

 slightly higher boiling points than hydrocarbons

 lower boiling points than alcohols

Thiols

-contain the sulfhydryl group

R –SH

-generally have a strong odour (ex. skunk, garlic, sewage, additive to natural gas)

-name by adding ending ``thiol``

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