PROBLEMS CH 14
PROBLEMS CH 14. Learning Check Identify the following compounds as either an aldehyde or ketone. A. CH 3 —CH 2 —CH 2 —COH B. CH 3 —CH 2 —CO—CH 2 —CH 2.
Jan 18, 2016
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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.
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