Organic Chemistry- Chapter 10

Alcohols

-OH bonded to an sp3 hybridized carbon

Hydroxyl group

True or False:

When naming an alcohol, the chain is numbered so that the carbon bearing the -OH group has the largest number

False

What two functional groups does -OH take precedence over when naming?

Alkyl and halogens

True or False:

When giving an alcohol its common name, name the alkyl group bonded to the -OH group and then add the word “alcohol”

True

A compound containing two hydroxyl groups

Diol

A compound containing three hydroxyl groupsd

Triol

A compound containing hydroxyl groups on adjacent carbons

Glycol

A compoun

Are alcohols polar or nonpolar?

Polar

Due to hydrogen bonding, the boiling points of alcohols are ______ than those of hydrocarbons of comparable molecular weight

Higher

Due to increased dispersion forces present in alcohols (due to polarity), the boiling point of alcohols _________ as molecular weight increases

Increases

True or False:

Alcohols can not hydrogen bond

False

Alcohols can hydrogen bond, so they are ____ soluble in water than hydrocarbons of comparable molecular weight

More

Each OH can participate in how many hydrogen bonds?

Three

True or False:

Alcohols can function as weak acids and weak bases

True

What is the pKa of alcohols?

16-18

Loss of a proton from an alcohol = ________ anion, which is a relatively ______ base

Alkoxide, strong

Is -OH2+ a good or poor leaving group?

Good

High molecular weight, water-soluble alcohols are slightly ______ acids than water

Weaker

In the presence of strong acids that generate hydronium ion, the O atom of an alcohol is a ____ and reacts with an ____ by proton transfer to form an _______ ion

Base; acid; oxonium

Alcohols react with active metals (Li, Na, & K) to liberate H2 and form _____ _________

Metal alkoxide

To name a metal alkoxide, first, name the ______, then the _____

Cation; anion

Alkoxides are similar or stronger in basicity to the _________ ion

Hydroxide

Name the following ion:

H:-

Hydride ion

Hydride ion (H:-) is the conjugate base of H2 and is an extremely ______ base

Strong

A common theme for reactions of alcohols is the conversion of the -OH group into a ______ leaving group by protonation and/or replacement with a _______ or other group

Better; halogen