ACT 11

Question 1

are organic derivatives of water, but they have two organic groups bonded to the same oxygen atom rather than one

the organic groups might be:
⮚alkyl,
⮚aryl, or
⮚vinylic, and
⮚the oxygen atom might be in an open chain or a ring

Answer 1

ethers

Question 2

• The boiling points of ethers are ________ to those of alkanes of comparable molecular mass and are much ______ than those of alcohols of comparable molecular mass.
• Ether oxygen atoms have NO hydrogen atom attached directly to them unlike ROH.

Answer 2

• similar
• lower

Question 3

⮚________ in water than alkanes of similar molecular mass because ether molecules are able to form hydrogen bonds with water

⮚ have water solubilities similar to those of alcohols of the same molecular mass

⮚ _________ substances tend to be more soluble in ethers than in alcohols because ethers have no hydrogen-bonding network that has to be broken up for solubility to occur

Answer 3

• more soluble
• Non-polar

Question 4

Volatile nature of ether:

⮚Ethers are the isomeric products of a _______ alcohol

⮚ The molecules are held together by ______ intermolecular forces

Answer 4

• monohydric
• weak

Question 5

C1-C2

C1-C4

Answer 5

• GAS
• liquid

Question 6

Chemical Properties

1. Resemble hydrocarbons in their resistance to chemical reaction.

⮚ For example, they do NOT react with oxidizing agents, such as _____________

• Likewise, they do not react with reducing agents such as ____ in the presence of a __________

⮚Furthermore, most acids and bases at moderate temperatures do NOT affect them.

Answer 6

• potassium dichromate
• H2; metal catalyst

Question 7

• Ethers are flammable.

⮚ Special care must be exercised in laboratories where ethers are used.

⮚ ________, whose boiling point of ___ is only a few degrees above room temperature, is a particular flashfire hazard.

• React slowly with oxygen from the air to form unstable _______ & _______

⮚ Such compounds, when concentrated, represent an explosion hazard and must be removed before stored ethers are used.

Answer 7

• Diethyl ether
• 35°C
• hydroperoxides and peroxides

Question 8

A chemical reaction for the preparation of ethers that was previously considered is the __________________ of a primary alcohol which will produce an ether.

alcohol + alcohol, heated = ether + water

Answer 8

• intermolecular dehydration

Question 9

A. Medical and Commercial Uses

1. Solvents (2)

Because of their general inertness to chemical reaction and their good solvent properties, ethers are ___________ in which to carry out many organic reactions.

Their relatively ____ boiling points simplify their separation from the reaction products.

Answer 9

1. Diethyl ether
2. tetrahydrofuran

• excellent solvents
• low B

Question 10

2. Anesthetics

⮚ In 1846 ________ reported the first use of __________ as a volatile inhaled agent to produce surgical anesthesia.

• This was followed by the introduction of ________, ________, & ______ in the 1950s.

⮚ Although neither ________ or ________ are in widespread clinical use today, they served as the structural templates for synthetic manipulations that have produced today’s potent congeners

⮚ The volatile anesthetics in common clinical use are either ___________ or ____________

Answer 10

• William Morton
• diethyl ether
• chloroform
• nitrous oxide
• halogenated hydrocarbons
• diethyl ether or chloroform
• halogen-substituted ethers or extensively halogenated alkanes.

Question 11

DIETHYL ETHER

ADVANTAGES:
*Easy administration, less danger of overdose since there is a large gap between the effective level for anesthesia and the lethal dose and readily made in pure form and causes excellent muscle relaxation

Answer 11

DISADVANTAGES:
*nausea and irritation of respiratory passage and highly flammable substance, forming explosive mixtures with air

Question 12

• less flammable
• better anesthetic properties and have more fluorine atoms and fewer chlorine atoms
• anesthesia can be achieved in less than 10 minutes
• with an inhaled concentration of 3% in oxygen

Answer 12

HALOGENATED ETHERS

Question 13

⮚ used to make perfumes, flavorings and as a solvent

⮚ AKA _________, __________

⮚ the anti-oxidant BHA (Butylated Hydroxy Anisole) is the derivative of anisole

Answer 13

• methoxybenzene
• methyl phenyl ether

SIMPLEST AROMATIC ETHER ANISOLE