problems ch 14. learning check identify the following compounds as either an aldehyde or ketone. a....

PROBLEMS CH 14

Learning Check

Identify the following compounds as either an aldehyde or ketone.

A. CH3—CH2—CH2—COH

B. CH3—CH2—CO—CH2—CH2—CH3

C.

D.

O

O

Solution

Identify the following compounds as either an aldehyde or ketone.

A. CH3—CH2—CH2—COH aldehyde

B. CH3—CH2—CO—CH2—CH2—CH3 ketone

C. ketone

D. aldehyde

O

O

Learning Check

Give the IUPAC name of the following aldehydes.CH3—CH—CH2—CH2—CHO

ClB.

A.

Solution

Give the IUPAC name of the following aldehydes.

Step 1 Name the longest carbon chain by replacing the -e in the alkane name with -al.

A. pentanal B. benzaldehyde

CH3—CH—CH2—CH2—CHO

Cl

A.

B.

Solution

Give the IUPAC name of the following aldehydes.

Step 2 Name and number the substituents by counting the carbonyl group as carbon 1.

A. 4-chloro-pentanal B. 2-ethyl-benzaldehyde

12

B.

A.5 4 3 2 1

CH3—CH—CH2—CH2—CHO

Cl

Classify each as an aldehyde or ketone.

Learning Check

O

A.

C.

B.

D.

Solution

O

Classify each as an aldehyde or ketone.

O

A.

C.

B.

D.

Ketone Aldehyde

Aldehyde Ketone

B. CH3─O─CH3A.

D.C.

Learning Check

Classify each as an aldehyde, ketone, alcohol,or ether.

Solution

B. CH3─O─CH3A.

D.C.

Ketone Ether

Aldehyde Alcohol

Classify each as an aldehyde, ketone, alcohol,or ether.

Learning Check

Name each of the following.

A.

B.

C.

Solution

Name each of the following.

A.

B.

C.

Pentanal

3-Chloropropanal

2-Butanone

Name the following compounds.

Learning Check

A. OB.

C.

Solution

A.

C.

2-Pentanone; methyl propyl ketone

OB.

3,3-Dimethylbutanal

Cyclohexanone

Name the following compounds.

Learning Check

Draw the condensed structural formulas for each of the following.A. 4-MethylpentanalB. 2,3-DichloropropanalC. 3-Methyl-2-butanone

Solution

A. 4-Methylpentanal

B. 2,3-Dichloropropanal

C. 3-Methyl-2-butanone

Draw the condensed structural formulas for each of the following.

Select the compound in each pair that would have thehigher boiling point. Explain. A. An alcohol forms hydrogen bonds.

B. There are dipole–dipole attractions between the carbonyl groups.

C.

Learning Check

O

CH3—CH2—CH3 or CH3—CH2—OH

CH3—CH2—OH CH3—O—CH3

or

or

Solution

Select the compound in each pair that would have thehigher boiling point. Explain. Higher Boiling Point ReasonA. CH3—CH2—OH An alcohol forms hydrogen bonds.

B. There are dipole–dipole attractions between the carbonyl groups.

C. CH3—CH2—OH An alcohol forms hydrogen bonds,

but an ether does not.

O

An alcohol forms hydrogenbonds.

There are dipole–dipole attractions between the carbonyl groups.

An alcohol forms hydrogen bonds, but an ether does not

CH3—CH2—OH

CH3—CH2—OH

Learning Check

Indicate if each of the following is or is not soluble in water.A. CH3—CH2—CH3

B. CH3—CH2—OH

C.

D.

Solution

Indicate if each of the following is or is not soluble in water.A. CH3—CH2—CH3

B. CH3—CH2—OH

C.

D.

not soluble in water

soluble in water

soluble in water

soluble in water

Learning Check

Write the condensed structural formula and the name of the oxidized product when each of the following is mixed with Tollens’ reagent.A. Butanal

B. Acetaldehyde

C. Ethyl methyl ketone

Solution

A. Butanal

B. Acetaldehyde

C. Ethyl methyl ketone

Butanoic acid

Ethanoic acid, acetic acid

Write the condensed structural formula and the name of the oxidized product when each of the following is mixed with Tollens’ reagent.

None. Ketones are not oxidized by Tollen’s reagent.

Learning Check

Predict the product for each of the following reactions.

A. + H2

B. + H2

CCH2

H2C

H3C

O

HO

Pt

Ni

Solution

Predict the product for each of the following reactions.

A. + H2

B. + H2

O

Pt

Ni

OH

CHCH2

H2C

H3C

OH

H

CCH2

H2C

H3C

O

H

Learning Check

Identify each as a hemiacetal or acetal.

SolutionIdentify each as a hemiacetal or acetal.

hemiacetal

acetal

Learning Check

Draw the condensed structural formula of the acetal formed by adding CH3OH to butanal.

Solution

Draw the condensed structural formula of the acetal formed by adding CH3OH to butanal.

© 2013 Pearson Education, Inc. Chapter 14, Section 1 29

Learning Check

Identify each as a chiral or achiral compound.

A. B. C.

H CH3

Cl

C

CH2 CH3

H CH3

Cl

C

Br

H CH3

Cl

C

H

© 2013 Pearson Education, Inc. Chapter 14, Section 1 30

Solution

Identify each as a chiral or achiral compound.

A. B. C.

H CH3

Cl

C

CH2 CH3

H CH3

Cl

C

Br

H CH3

Cl

C

H

chiral chiral antichiral

© 2013 Pearson Education, Inc. Chapter 14, Section 1 31

Learning Check

Indicate whether each of the following pairs of Fischer

projections can or cannot be superimposed.

CH2 OH

H CH3

Br

CH2 OH

H3C H

Br

and

H

H CH3

Br

H

H3C H

Br

and

A.

B.

© 2013 Pearson Education, Inc. Chapter 14, Section 1 32

Solution

Indicate whether each of the following pairs of Fischer

projections can or cannot be superimposed:

cannot be superimposed

can be superimposed

CH2 OH

H CH3

Br

CH2 OH

H3C H

Br

and

H

H CH3

Br

H

H3C H

Br

and

A.

B.

© 2013 Pearson Education, Inc. Chapter 14, Section 1 33

Learning Check

Identify the following as a D or L isomer.

CHO

OHH

HHO

HHO

OHH

CH2OH

© 2013 Pearson Education, Inc. Chapter 14, Section 1 34

Solution

Identify the following as a D or L isomer.

CHO

OHH

HHO

HHO

OHH

CH2OH

The –OH group ison the right, it is a D isomer.