10. Use the dash-wedge method to draw the 3-D structure of ammonia. a) What is the name of this type of structure? Trigonal Pyramidel b) What is the hybridization state of the N? s 11. Label all the nitrogens as 1°, 2°, or 3° then place the following labels on the molecules: (Aromatic or Nonaromatic) and (Amine or Amide). 20 Amine Aromatic EN Amide nonaromatic H N CH₂CH3 CH₂CH3 Amine Nonoramatic More acidic hydrogens re present in Pyrrole. NH₂ Amide nonaromatic NH₂ Amine Aromatic Aminc nonaromatic .N N. NH -NH Amine Non-aromatic IZ 12. Which of the following aromatic compounds (pyridine or pyrrole) is more basic? Explain. (Hint-think about the hybridization of each atom) Amine Nonaromatic

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661
10. Use the dash-wedge method to draw the 3-D structure of ammonia.
a) What is the name of this type of structure? Trigonal Pyramidel
b) What is the hybridization state of the N? S
२०
11. Label all the nitrogens as 1º, 2º, or 3° then place the following labels on the molecules:
(Aromatic or Nonaromatic) and (Amine or Amide).
Aminc
Aromatic
2⁰
030
Amide
nonaromatic
N
H-N-H
Z-H
More acidic hydrogens
are present in pyrrole.
00
H-N-H
CH3
10
Model 3: Amine Alkylation
H
N.
CH₂CH3
CH₂2CH3
H-N-CH3 Br-CH3
BJ
CH3
Br-CH3
Br-CH3
nonaromatic
fast
RXN 1A
faster
RXN 2A
fastest
Amine
Nonoromatic
RXN 3A
NH₂
12. Which of the following aromatic compounds (pyridine or pyrrole) is more basic?
Explain. (Hint-think about the hybridization of each atom)
N
+!
H-N-H
CH3
-Z-H
H
(+)ī
H-N-CH₂
CH3
2⁰
NH₂
30
I
I-Z:
Aminc
nonaromatic
H
IZ
H
N
H-N-H
30
Amine
Aromatic
H-N-H
CH3
0
H
+i
H3C-N-CH, H-N-CH3
CH3
CH3
O
NH
N.
RXN 1B
RXN 2B
4\\\\
RXN 3B
२०
ភ
H-N-H
1
CH3
-H
NH
Amine
Non-aromatic
bb b
po
IZ
Amine
Nonaromatic
+i
H-N-H
I-Z-H
H3C-N-CH3
CH3
3º
H
H-N-CH3 H-N-H
I
CH3
CH3
O
0°
H
H-N-CH3
CH3
Br
Br
Br
Transcribed Image Text:661 10. Use the dash-wedge method to draw the 3-D structure of ammonia. a) What is the name of this type of structure? Trigonal Pyramidel b) What is the hybridization state of the N? S २० 11. Label all the nitrogens as 1º, 2º, or 3° then place the following labels on the molecules: (Aromatic or Nonaromatic) and (Amine or Amide). Aminc Aromatic 2⁰ 030 Amide nonaromatic N H-N-H Z-H More acidic hydrogens are present in pyrrole. 00 H-N-H CH3 10 Model 3: Amine Alkylation H N. CH₂CH3 CH₂2CH3 H-N-CH3 Br-CH3 BJ CH3 Br-CH3 Br-CH3 nonaromatic fast RXN 1A faster RXN 2A fastest Amine Nonoromatic RXN 3A NH₂ 12. Which of the following aromatic compounds (pyridine or pyrrole) is more basic? Explain. (Hint-think about the hybridization of each atom) N +! H-N-H CH3 -Z-H H (+)ī H-N-CH₂ CH3 2⁰ NH₂ 30 I I-Z: Aminc nonaromatic H IZ H N H-N-H 30 Amine Aromatic H-N-H CH3 0 H +i H3C-N-CH, H-N-CH3 CH3 CH3 O NH N. RXN 1B RXN 2B 4\\\\ RXN 3B २० ភ H-N-H 1 CH3 -H NH Amine Non-aromatic bb b po IZ Amine Nonaromatic +i H-N-H I-Z-H H3C-N-CH3 CH3 3º H H-N-CH3 H-N-H I CH3 CH3 O 0° H H-N-CH3 CH3 Br Br Br
Model 2: pKa Values for Various Nitrogen Compounds
요
pKa values for
the conjugate
acid
Name:
NH₂
0
least basic
ethanamide
4.6
NH₂
analine
R-C
H-Z
N-H
HH
H
9.3
ammonia
•Resonance is preffered and performed first
Over attaching nitrogen and hydrogen.
The benzene must remain intact.
Critical Thinking Questions
3. Draw in any lone pairs on the structures in Model 2.
4. According to the pKa values, label the most and least basic compounds.
5. Below each compound place the name of the structure. (The first has been done)
6.
We have seen that alky groups are electron-donating.
quino 501 Wed
NH₂
a. Construct an explanation for why the lone pair on ethyl amine is more likely to make a
bond to H+ than the lone pair on the ammonia.
Decause ammonia is too large and it won't attach easily.
10.8
most basic
HO
b. Draw diethyl amine and ethyl amine and discuss which one is the stronger base.
Explain your reasoning.
ethyl amine.
I
TNH₂
w
There are less acidic hydrogens Present which makes Dimethyl ammines stronger bases.
c. Draw the second-order resonance structures for aniline and explain why the lone pair
on the nitrogen is less likely to form a bond to H+.
Nit₂
+N//2
Transcribed Image Text:Model 2: pKa Values for Various Nitrogen Compounds 요 pKa values for the conjugate acid Name: NH₂ 0 least basic ethanamide 4.6 NH₂ analine R-C H-Z N-H HH H 9.3 ammonia •Resonance is preffered and performed first Over attaching nitrogen and hydrogen. The benzene must remain intact. Critical Thinking Questions 3. Draw in any lone pairs on the structures in Model 2. 4. According to the pKa values, label the most and least basic compounds. 5. Below each compound place the name of the structure. (The first has been done) 6. We have seen that alky groups are electron-donating. quino 501 Wed NH₂ a. Construct an explanation for why the lone pair on ethyl amine is more likely to make a bond to H+ than the lone pair on the ammonia. Decause ammonia is too large and it won't attach easily. 10.8 most basic HO b. Draw diethyl amine and ethyl amine and discuss which one is the stronger base. Explain your reasoning. ethyl amine. I TNH₂ w There are less acidic hydrogens Present which makes Dimethyl ammines stronger bases. c. Draw the second-order resonance structures for aniline and explain why the lone pair on the nitrogen is less likely to form a bond to H+. Nit₂ +N//2
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