Wade - Organic Chemistry 9th Edition - Chapter 2

Skip to main content

My Courses

Calculators AI Tools Study Prep Blog Study Prep Home

Ch. 2 - Acids and Bases; Functional Groups

Back

Wade 9th Edition

Ch. 2 - Acids and Bases; Functional Groups

Problem 16b
Give the structures of their conjugate acids, and estimate their pK_as from similar compounds in Appendix 4.
Problem 17a,b
Consider each pair of bases, and explain which one is more basic. Draw their conjugate acids, and show which one is a stronger acid.
(a)
(b)
Problem 18
Which is a stronger base: ethoxide ion or acetate ion? Give pK_b values (without looking them up) to support your choice.
Problem 20a
Acetic acid can also react as a very weak base (pK_b = 20). Two different sites on acetic acid might become protonated to give the conjugate acid. Draw both of these possible conjugate acids, and explain (resonance) why the correct one is more stable. Calculate the pK_a of this conjugate acid.
Problem 21a,b,c
Choose the more acidic member of each pair of isomers, and show why the acid you chose is more acidic.
(a)
(b)
(c)
Problem 21d,e
Choose the more acidic member of each pair of isomers, and show why the acid you chose is more acidic.
(d)
(e)
Problem 21f,g
Choose the more acidic member of each pair of isomers, and show why the acid you chose is more acidic.
(f)
(g)
Problem 22a,b
Choose the more basic member of each pair of isomers, and show why the base you chose is more basic.
(a)
(b)
Problem 22c,d
Choose the more basic member of each pair of isomers, and show why the base you chose is more basic.
c.
d.
Problem 22e
Choose the more basic member of each pair of isomers, and show why the base you chose is more basic.
e.
Problem 23a
In the following acid–base reactions,
1. draw Lewis structures of the reactants and the products.
2. determine which species are acting as electrophiles (acids) and which are acting as nucleophiles (bases).
3. use the curved-arrow formalism to show the movement of electron pairs in these reactions, as well as the imaginary movement in the resonance hybrids of the products.
4. indicate which reactions are best termed Brønsted–Lowry acid–base reactions.
(a)
Problem 23b
In the following acid–base reactions,
1. draw Lewis structures of the reactants and the products.
2. determine which species are acting as electrophiles (acids) and which are acting as nucleophiles (bases).
3. use the curved-arrow formalism to show the movement of electron pairs in these reactions, as well as the imaginary movement in the resonance hybrids of the products.
4. indicate which reactions are best termed Brønsted–Lowry acid–base reactions.
(b)
Problem 24a,b,c
Classify the following hydrocarbons, and draw a Lewis structure for each one. A compound may fit into more than one of the following classifications:
alkane
alkene
alkyne
cycloalkane
cycloalkene
cycloalkyne
aromatic
hydrocarbon
a. (CH₃CH₂)₂CHCH(CH₃)₂
b. CH₃CHCHCH₂CH₃
c.. CH₃CCCH₂CH₂CH₃
Problem 24d,e,f
Classify the following hydrocarbons, and draw a Lewis structure for each one. A compound may fit into more than one of the following classifications:
alkane
alkene
alkyne
cycloalkane
cycloalkene
cycloalkyne
aromatic
hydrocarbon
(d)
(e)
(f)
Problem 24g,h,i
Classify the following hydrocarbons, and draw a Lewis structure for each one. A compound may fit into more than one of the following classifications:
alkane
alkene
alkyne
cycloalkane
cycloalkene
cycloalkyne
aromatic
hydrocarbon
(g)
(h)
(i)
Problem 25a,b,c
Draw a Lewis structure, and classify each of the following compounds. The possible classifications are as follows:
alcohol
ether
ketone
aldehyde
carboxylic acid
alkene
(a) CH₂CHCHO
(b) CH₃CH₂CH(OH)CH₃
(c) CH₃COCH₂CH₃
Problem 25d,e
Draw a Lewis structure, and classify each of the following compounds. The possible classifications are as follows: alcohol ether ketone aldehyde carboxylic acid alkene
(d) CH₃CH₂OCHCH₂
(e)
Problem 25f,g
Draw a Lewis structure, and classify each of the following compounds. The possible classifications are as follows:
alcohol
ether
ketone
aldehyde
carboxylic acid
alkene
(f)
(g)
Problem 25h,i
Draw a Lewis structure, and classify each of the following compounds. The possible classifications are as follows:
alcohol
ether
ketone
aldehyde
carboxylic acid
alkene
(h)
(i)
Problem 26a,b
Draw a Lewis structure, and classify each of the following compounds:
(a) CH₃CH₂CONHCH₃
(b) (CH₃CH₂)₂NH
Problem 26c,d
Draw a Lewis structure, and classify each of the following compounds:
(c) (CH₃)₂CHCOOCH₃
(d) CH₃CHCHCOCl
Problem 26e,f
Draw a Lewis structure, and classify each of the following compounds:
(e) (CH₃CH₂)₂O
(f) CH₃CH₂CH₂CN
Problem 26g,h
Draw a Lewis structure, and classify each of the following compounds:
(g) (CH₃)₃CCH₂CH₂COOH
(h)
Problem 26i,j
Draw a Lewis structure, and classify each of the following compounds:
(i)
(j)
Problem 26k,l
Draw a Lewis structure, and classify each of the following compounds:
(k)
(l)
Problem 26m,n,o
Draw a Lewis structure, and classify each of the following compounds:
(m)
(n)
(o)
Problem 27a,b,c
Circle the functional groups in the following structures. State to which class (or classes) of compounds the structure belongs.
a. CH₂=CHCH₂COOCH₃
b. CH₃OCH₃
c. CH₃CHO
Problem 27d,e,f
Circle the functional groups in the following structures. State to which class (or classes) of compounds the structure belongs.
d. CH₃CONH₂
e. CH₃NHCH₃
f. RCOOH
Problem 27g,h,i
Circle the functional groups in the following structures. State to which class (or classes) of compounds the structure belongs.
(g)
(h)
(i)
Problem 28
The C≡N triple bond in acetonitrile has a dipole moment of about 3.6 D and a bond length of about 1.16 Å. Calculate the amount of charge separation in this bond. How important is the charge-separated resonance form in the structure of acetonitrile?