Unit 9-10 Knewton

Which of the following molecules is not an aldehyde?

(CH3)3COH CH2COCH2

Ketones contain an oxygen atom. Ketones have higher boiling points than the corresponding alkanes. Ketones contain a carbonyl group between two carbon substituents.

(CH3)3COH CH3CH2CHO HCHO

Most alcohols are not Arrhenius bases. Bases like NaOH and KOH have OH− ions, while the defining feature of an alcohol is the __________ group.

-OH

What is the IUPAC name for CH3−CH2−O−(CH2)3−CH3?

1-ethoxybutane

Identify the name of an alcohol with three carbons and a single (−OH) group on the third carbon in the chain.

1-propanol

Identify the name of an alcohol with four carbons in a chain and an (−OH) group on the second carbon.

2-butanol

What is the IUPAC name for CH3−O−CH(CH3)−CH2−CH3?

2-methoxybutane

What is the IUPAC name for CH3−O−CH(CH3)−(CH2)2−CH3?

2-methoxypentane

What is the name of a secondary alcohol with the formula C3H7OH?

2-propanol

What is the name for the compound CH3CH2C(O)CH2CH2CH2CH3?

3-heptanone

CH3CH2CH2C(O)CH2CH3 is called:

3-hexanone

The term carbonyl group best fits which of the following descriptions?

A carbonyl group is a carbon atom double bonded to an oxygen atom.

What are the products formed by the base hydrolysis of amides?

A carboxylate salt and an amine

Which term is best described as an organic compound containing a carbonyl group bound to two hydrogen atoms or to a hydrogen atom and an alkyl substituent?

Aldehyde

Which of the following is a characteristic of aldehydes?

Aldehydes contain an oxygen atom. The carbonyl group in an aldehyde must be attached to a hydrogen atom.

Which of the following alcohols is a liquid at room temperature? ethanol butanol methanol

All of the above

Which of the following best describes the term aldehyde?

An aldehyde is an organic compound containing a carbonyl group attached to a hydrogen.

An ether is described by which of the following?

An ether is an organic compound with an oxygen atom bound to two carbon atoms.

What amine and carboxylic acid can be used to synthesize N−ethylbutanamide? CH3−CH2−CH2−O||C−N|H−CH2CH3

Butanoic acid and ethylamine

Give the chemical formula of the alcohol that results from the reduction of n-pentanoic acid.

CH3CH2CH2CH2CH2OH

Which of the following is an ether?

CH3CH2OCH2CH3

Give the chemical formula of the alcohol that results from the reduction of ethanoic acid.

CH3CH2OH

Which of the following is the formula for the simplest ketone?

CH3COCH3

Write the products of the acid hydrolysis of the ester with the formula CH3COOCH(CH3)2. Use chemical symbols. For the first product fill in the remaining part of the acid formula. For the second product fill in the whole formula for the alcohol.

CH3COOCH(CH3)2 + H2O <- CH3COOH + (CH3)2 CHOH

Identify the structure of an ester that undergoes hydrolysis with base sodium hydroxide to produce sodium acetate and ethanol.

CH3COOCH2CH3

Write the chemical formula for methanol.

CH3OH

Identify the correct product(s) for the reduction of hexanoic acid.

CH3−CH2−CH2−CH2−CH2−C||O−H CH3−CH2−CH2−CH2−CH2−CH2−OH

CH3−CH2−CH2−CH2−CH2−O||C−NH2+HCl→______+NH4Cl What is the unidentified product of the reaction?

CH3−CH2−CH2−CH2−CH2−O||C−OH

CH3−CH2−CH2−O∥C−CH3|N|CH3+H2O+HCl→________+NH+4Cl− What is the unidentified product of the reaction?

CH3−CH2−CH2−COOH

What is the the most widely used ether?

Diethyl ether

Which intermolecular interactions are responsible for the solubility of ethanol in an alkane solvent?

Dispersion Forces

Which of the following types of compounds is used to increase the oxygen content of gasoline?

Ether

What is the IUPAC name for CH3CH2OCH2CH3?

Ethoxyethane

What is the common name for CH3OCH2CH3?

Ethylmethyl ether

Which of the following is the simplest aldehyde (formaldehyde)?

H2CO

What kind of intermolecular interactions could molecules of ethanol have when within pure liquid ethanol?

Hydrogen Bonds Dispersion Forces

Which of the following is a characteristic of ketones?

Ketones contain an oxygen atom. Ketones have higher boiling points than the corresponding alkanes. Ketones contain a carbonyl group between two carbon substituents.

Ethanol (CH3CH2OH) has a higher boiling point than dimethyl ether (CH3OCH3) because the ether is

Less polar

Aldehydes have which of the following intermolecular forces?

London dispersion forces Dipole-dipole interactions

What is the IUPAC name for CH3OCH2CH3?

Methoxyethane

Complete the missing components of the products in the acid hydrolysis of methyl butanoate below. For the first product fill in the remaining part of the acid formula, and for the second fill in the remaining part of the alcohol formula. Methyl butanoate + H2O <- ------------COOH + ----OH

Methyl butanoate + H2O <- CH3CH2CH2COOH + CH3OH

What will form when butanoic acid and diethylamine react?

N,N-diethylbutanamide and water

What are the products of the reaction of propanoic acid with methylamine? CH3−CH2−C||O−OH+N|H|H−CH3⟶_______+_______

N-methylpropanamide and water

In an aldehyde, the carbonyl carbon must be connected to:

No more than one carbon

In any ether, the alkyl groups must be: identical nonidentical linear

None of the above

In a reaction that produces an ether:

One water molecule is formed and eliminated from two molecules of alcohol

Aldehydes can be synthesized from primary alcohols through which of the following?

Oxidation

CH3CH2CH2C(O)CH3 is called

Pentanone

What are the products formed during base hydrolysis of methyl ethanoate with potassium hydroxide?

Potassium salt and methanol

In a ketone, the carbonyl carbon must be connected to:

Precisely two carbons

Classify the alcohol as primary, secondary, or tertiary. 2-methylpropan-1-ol

Primary alcohol

Which of the following classes of alcohols will oxidize to form an aldehyde?

Primary alcohol

Which of the following alcohol structures is not a secondary alcohol? Propan-1-ol Propan-2-ol Butan-2-ol Pent-3-ol

Propan-1-ol

What is the name for CH3CH2CHO?

Propanal

What type of bonds are formed within the hybridized orbitals of a carbonyl group?

Sigma

The relative stability of the hydroxide ion, OH−, allows alcohols to undergo what process?

Substitution and dehydration reactions

3-methyl-3-heptanol is a __________.

Tertiary alcohol

The melting point of phenol is 40.5∘C and that of toluene is −95∘C. What is the best explanation for this difference?

The (−OH) group on phenol can form hydrogen bonds, and the −CH3 group on toluene cannot.

The boiling point of xylenol (2,6-dimethylphenol) is 203∘C, whereas the boiling point of 1,2,4-trimethylbenzene is 169∘C. What can you conclude from this comparison of the boiling points? Select the best choice below.

The (−OH) group on xylenol increases the boiling point.

Phenols do not completely dissociate in water, but they are much stronger acids than aliphatic alcohols. Identify the correct reason for this characteristic of phenol.

The aromatic ring delocalizes and stabilizes the negative charge on the oxygen in the phenoxide ion.

Which of the following statements is NOT true about phenol?

The aromatic ring delocalizes and stabilizes the negative charge on the oxygen in the phenoxide ion. Therefore, phenols completely dissociate in water.

Choose the options below that are characteristics unique to ketones. (select all that apply).

The functional group contains only carbon and oxygen They are prepared by oxidizing alcohols whose −OH functional group is located on a carbon atom in the middle of the carbon chain. They can be used as pharmaceutical and chemical solvents, and as paint and varnish removers.

Choose the option below that is a characteristic of ketones.

The functional group of this type of compound must always be in the middle of a carbon chain.

A deuterium-labeled alcohol, R−OD , would rapidly convert to R−OH in water as the deuterium is lost to the water. How is this possible?

The hydroxyl group can exchange protons with water because it is weakly acidic.

Which among the following is NOT true for phenols?

They are more basic than aliphatic alcohols.

Choose the options below that are characteristics unique to aldehydes.

They are prepared by oxidizing alcohols whose −OH functional group is located on a carbon atom in the end of the carbon chain. They are named using the suffix -al. A common aldehyde, formaldehyde, can stop many of the biological processes that cause tissue to decay.

Identify the options below that are not characteristics of ethers. (select all that apply)

They each contain a carbonyl group. Each contains the functional group −O− attached to hydrogen atoms via single bonds. They do not contain oxygen.

What is the geometry of a carbonyl group?

Trigonal Planar

Ethers have the general formula ROR and alcohols have the general formula ROH.

True

Ethers can be obtained by reacting:

Two alcohols

During hydrolysis, when strong acid reacts with ester it forms alcohol and __________.

a carboxylic acid

Identify the statement(s) that is/are correct with reference to saponification process. a. An ester is hydrolyzed in a strong base solution. The products are a carboxylate salt and an alcohol. b. It is a process of making soap by reacting a strong base with a long-chain fatty acid. c. The reactions are reversible.

a. An ester is hydrolyzed in a strong base solution. The products are a carboxylate salt and an alcohol. b. It is a process of making soap by reacting a strong base with a long-chain fatty acid.

What are the products formed when N-methylbutanamide is hydrolyzed by a base?

butanoate and methylamine

Complete the missing components in the base hydrolysis of n-propyl ethanoate below.

n-propyl ethanoate + KOH -> CH3COO-K+ +CH3CH2CH2OH

The unhybridized p orbital of the carbon in a carbonyl group interacts with the p orbital in oxygen forming what type of bond?

π