Collection of molecular structures illustrating different types of chemical species, including ions, radicals, and functional groups.
Chemical structures of various organic and inorganic molecules and ions, including carbocations, carbanions, radicals, and functional groups such as amines, ethers, nitriles, and phosphines.
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Show Answer Key & Explanations
Step-by-step solution for: 10: Lewis Structures - Chemistry LibreTexts
▼
Show Answer Key & Explanations
Step-by-step solution for: 10: Lewis Structures - Chemistry LibreTexts
It looks like you've uploaded a set of chemical structures labeled from a to o, and each structure involves atoms with formal charges or specific bonding patterns. However, since I can't view images directly, your description is limited to the text-based representation provided.
From what you've included, it appears that these are molecular structures (some with formal charges), and the task likely involves:
- Identifying formal charges
- Determining correct Lewis structures
- Evaluating resonance forms
- Or possibly identifying polarity, acidity/basicity, or hybridization
Let’s go through each one carefully and analyze them step by step based on standard rules of organic chemistry.
---
We'll evaluate:
- Formal charge
- Validity of the structure
- Whether it's a reasonable resonance form or ion
---
#### a.
```
H
/
C⁺
/ \
H H
```
- Central carbon has 3 bonds and a +1 formal charge.
- Carbon normally has 4 bonds; here only 3 → electron-deficient.
- This is the methyl cation (CH₃⁺) — a carbocation.
- Valid species, though highly reactive.
- Formal charge: +1 on C
✔ Valid (carbocation)
---
#### b.
```
H
/
C⁻
/ \
H H
```
- Carbon has 3 bonds and a –1 formal charge.
- Total valence electrons: C = 4, 3×H = 3 → total 7 electrons.
- But in this drawing, only 6 electrons shown (3 bonds = 6 e⁻).
- The negative charge implies an extra electron → total 8 electrons, so lone pair should be present.
- But no lone pair shown → incorrect Lewis structure.
✘ Invalid: missing lone pair on carbon.
Correct version would have a lone pair:
```
H
/
C⁻
/ \
H H
```
with two dots on C.
✔ Corrected: methyl anion (CH₃⁻), valid but unstable.
---
#### c.
```
H
/
C⁻
/
H
```
- Only two bonds shown → only 2 bonds to C.
- But carbon has 4 valence electrons.
- With –1 charge, it has 5 electrons.
- Needs two more bonds or lone pairs.
- As drawn: only 2 bonds → only 4 electrons shared → incomplete octet.
✘ Invalid: incomplete structure.
Should be CH₃⁻ (same as b) or maybe a carbanion with lone pair and two H’s.
Possibly typo? Should be same as b?
---
#### d.
```
D⁻—O⁺=O
```
- D = deuterium (²H), isotopic hydrogen.
- O⁺=O: oxygen with +1 charge double-bonded to another oxygen?
- This looks like peroxide-like, but unusual.
- Left oxygen: bonded to D⁻ and double bond to O⁺ → 3 bonds.
- Right oxygen: double bond to left O, and +1 charge → only 2 electrons in bonds, but needs 8.
Wait — let's count:
- Left O: bonded to D⁻ (single), and double bond to O → 3 bonds = 6 electrons.
- Plus negative charge on D, positive on right O.
But D⁻ is deuteride ion, which is rare.
This might represent deuterium oxide with charge separation? But not stable.
Alternatively, could be D–O–O⁺ with resonance?
But D–O–O⁺ doesn’t make sense unless it's a radical or something.
More likely: misdrawn peroxide ion.
Standard peroxide: O–O²⁻
Here: D⁻–O⁺=O → suggests D–O–O, with charges.
But O⁺=O is like ozone or superoxide?
Wait — perhaps it's D–O–O⁺, but O⁺ is unusual.
Actually, this may be a resonance form of hydroperoxide?
But D⁻–O–O⁺ is not favorable due to charge separation.
Also, D⁻ is very strong base — unlikely.
✘ Unlikely to be stable or correct.
Possible misrepresentation.
---
#### e.
```
H₃C–N⁻–H
|
H
```
- Methylamine with negative charge on nitrogen.
- Nitrogen has three bonds (to C, H, H) and a –1 charge → must have lone pair.
- Valence: N has 5 electrons; 3 bonds = 6 e⁻ shared, plus 2 lone pair e⁻ → total 8.
- Charge: 5 valence - (3 bonds + 1 lone pair = 4 electrons assigned) → formal charge = 5 - (3 + 2) = 0? Wait.
Wait: Formal charge formula:
> FC = valence e⁻ - (number of bonds + number of lone pair e⁻)
Better:
> FC = V - (L + B)
Where:
- V = valence electrons
- L = lone pair electrons
- B = number of bonds (each bond counts as 1)
For N:
- V = 5
- Bonds: 3 (to C, H, H)
- Lone pair: 2 electrons → L = 2
- So FC = 5 - (2 + 3) = 0
But here it shows N⁻, so charge is –1.
So if N has three bonds and a lone pair, FC = 0.
To get –1, N must have four lone pair electrons → two lone pairs, and only two bonds.
But here it has three bonds → so cannot have –1 charge unless it's a different structure.
Wait — structure is:
```
H₃C–N⁻–H
|
H
```
That’s three bonds to N: C, H, H → 3 bonds → 6 bonding electrons.
And negative charge → so total electrons around N = 8 → so one lone pair.
Then formal charge = 5 - (1 lone pair × 2 + 3 bonds) = 5 - (2 + 3) = 0
But it shows N⁻, so charge is incorrectly labeled.
✔ Actually, this is methylamine (CH₃NH₂), neutral.
✘ So N⁻ is wrong — should be neutral.
Unless it's methanamine anion, but then N would need four bonds or more.
No — impossible for neutral N with three bonds and –1 charge.
Thus, this structure is invalid.
Correct: CH₃NH₂, neutral.
So e is incorrect.
---
#### f.
```
H₃C–N–H
|
H
```
- Same as e, but no charge.
- This is methylamine (CH₃NH₂).
- Nitrogen has three bonds and a lone pair → neutral.
- ✔ Valid and common molecule.
---
#### g.
```
H₃C–O–CH₃
```
- Dimethyl ether.
- Oxygen has two single bonds to CH₃ groups.
- Oxygen has two lone pairs.
- Neutral molecule.
- ✔ Valid.
---
#### h.
```
CH₃
|
CH₃–P–CH₃
```
- Trimethylphosphine (P(CH₃)₃).
- Phosphorus has three bonds, and one lone pair.
- P valence = 5 → 3 bonds = 3 e⁻ used, lone pair = 2 e⁻ → total 5 → neutral.
- ✔ Valid.
Note: P can expand octet, but here it's fine.
---
#### i.
```
H₃C–S–CH₃
```
- Dimethyl sulfide.
- Sulfur has two bonds, two lone pairs.
- S valence = 6 → 2 bonds = 4 e⁻, lone pairs = 4 e⁻ → total 8 → neutral.
- ✔ Valid.
---
#### j.
```
H₃C–C≡N⁺–H
```
- Wait: C≡N⁺–H → nitrogen triple bonded to carbon, and bonded to H, with +1 charge on N?
But nitrogen can't have five bonds.
Structure: H₃C–C≡N–H, with + on N?
But N has:
- Triple bond to C → 3 bonds
- Single bond to H → 1 bond
- Total 4 bonds → 8 electrons → but N only has 5 valence electrons.
So formal charge:
- V = 5
- Bonds = 4 → 4 electrons counted
- Lone pairs? None shown → 0
- FC = 5 - (0 + 4) = +1 → yes, possible.
But is this a real compound?
This is acetonitrile with protonated nitrogen?
But acetonitrile is CH₃–C≡N (neutral).
Protonating nitrile gives [CH₃–C≡N–H]⁺, which is a nitrilium ion.
Yes! This is protonated acetonitrile, or nitrilium ion.
But nitrilium ions are very electrophilic and usually stabilized by resonance.
But yes, possible.
So: CH₃–C≡N⁺–H → nitrilium ion, with positive charge on N.
✔ Valid, though unstable.
---
#### k.
```
H₃C–N=O
```
- Nitrosomethane.
- Nitrogen bonded to CH₃ and double bond to O.
- Nitrogen has 3 valence electrons? No — N has 5.
Structure: CH₃–N=O
- N has two bonds: one single to C, one double to O → 3 bonds → 6 electrons.
- N needs 8 → so must have one lone pair.
Formal charge:
- V = 5
- Bonds = 3 (count as 3)
- Lone pair = 2 electrons → L = 2
- FC = 5 - (2 + 3) = 0
So neutral.
But actual nitrosomethane is CH₃–N=O, and nitrogen is neutral, but oxygen is partially negative, and nitrogen is electrophilic.
Yes, valid.
But note: resonance exists: CH₃–N⁺=O⁻ ↔ CH₃–N=O with formal charges.
So both resonance forms possible.
✔ Valid.
---
#### l.
```
H₃C–C≡N
```
- Acetonitrile.
- Carbon triple bonded to N, single bond to CH₃.
- Terminal carbon (of CN): triple bond to N, single to C → 4 bonds → neutral.
- Nitrogen: triple bond → 3 bonds → needs lone pair → one lone pair → neutral.
- ✔ Valid.
---
#### m.
```
O⁻
/
H₃C–N⁺–O
\
O
```
Wait — structure is:
```
O⁻
/
H₃C–N⁺–O
\
O
```
But written as:
```
H₃C–N⁺–O
\
O
```
and above: O⁻
So likely:
```
O⁻
/
H₃C–N⁺–O
\
O
```
But that's three oxygens attached to N?
Wait — probably meant to be nitromethane:
```
O
║
H₃C–N⁺–O⁻
║
O
```
But here it's shown as:
```
H₃C–N⁺–O
\
O
```
and above: O⁻
Ah — probably meant:
```
O⁻
/
H₃C–N⁺–O
\
O
```
But that’s three oxygen atoms on N → NO₃⁻ like?
Wait — no.
Actually, nitromethane is CH₃–NO₂, with resonance:
```
O⁻
/
CH₃–N⁺=O
\
O
```
or
```
O
║
CH₃–N⁺–O⁻
\
O
```
But here it's shown as:
```
H₃C–N⁺–O
\
O
```
with O⁻ above.
So likely: CH₃–N⁺(O⁻)(=O) → nitromethane, with one O⁻ and one O=O?
Wait — no.
Standard resonance form of nitromethane:
```
O⁻
/
H₃C–N⁺=O
```
But here it's shown with two oxygens bonded to N, and one O⁻, one double bond?
Wait — the drawing is:
```
O⁻
/
H₃C–N⁺–O
\
O
```
So three bonds from N to O? That’s impossible.
Wait — perhaps it's:
```
O⁻
/
H₃C–N⁺=O
```
and the other O is part of the double bond?
But in text, it says:
```
H₃C–N⁺–O
\
O
```
and above: O⁻
So likely misdrawn.
Probably meant to be:
```
O⁻
/
H₃C–N⁺=O
```
Which is one resonance form of nitromethane.
Yes — CH₃NO₂, with N⁺ and O⁻.
✔ Valid resonance form.
---
#### n.
```
H₂C=N⁺=N⁻
```
- Diazo compound: diazomethane.
- H₂C=N⁺=N⁻
- Carbon: two H, double bond to N → 4 bonds → neutral.
- First N: double bond to C, double bond to N → 4 bonds → but N has 5 valence electrons → formal charge?
Calculate:
- N₁ (middle): bonded to C (double), and N (double) → 4 bonds → 4 electrons → FC = 5 - (0 + 4) = +1 → yes.
- N₂ (terminal): double bond to N → 2 bonds → but has –1 charge → so must have two lone pairs.
So: H₂C=N⁺=N⁻
This is diazomethane, CH₂=N₂, which is a known compound.
Yes — valid.
✔ Valid.
---
#### o.
```
H₂N–NH₂
```
- Hydrazine.
- Two NH₂ groups linked by N–N bond.
- Each nitrogen has three bonds (two H, one N) and a lone pair.
- Neutral molecule.
- ✔ Valid.
---
| Letter | Structure | Valid? | Comments |
|-------|----------|--------|--------|
| a | CH₃⁺ | ✔ | Methyl cation |
| b | CH₃⁻ | ✘ | Missing lone pair; should be CH₃⁻ with lone pair |
| c | CH₂⁻ | ✘ | Incomplete; should be CH₃⁻ |
| d | D⁻–O⁺=O | ✘ | Unstable charge separation; likely invalid |
| e | CH₃–N⁻–H₂ | ✘ | N has three bonds and –1 charge → formal charge should be 0; incorrect labeling |
| f | CH₃–NH₂ | ✔ | Methylamine |
| g | CH₃–O–CH₃ | ✔ | Dimethyl ether |
| h | P(CH₃)₃ | ✔ | Trimethylphosphine |
| i | CH₃–S–CH₃ | ✔ | Dimethyl sulfide |
| j | CH₃–C≡N⁺–H | ✔ | Nitrilium ion |
| k | CH₃–N=O | ✔ | Nitrosomethane |
| l | CH₃–C≡N | ✔ | Acetonitrile |
| m | CH₃–N⁺(O⁻)=O | ✔ | Resonance form of nitromethane |
| n | H₂C=N⁺=N⁻ | ✔ | Diazomethane |
| o | H₂N–NH₂ | ✔ | Hydrazine |
---
The task was likely to identify which structures are valid (correct Lewis structures), or assign formal charges, or evaluate resonance.
Based on analysis:
- Valid structures: a, f, g, h, i, j, k, l, m, n, o
- Invalid or incorrectly drawn: b, c, d, e
But if the task was to assign formal charges, then:
For example:
- a: C⁺ → formal charge +1
- b: C⁻ → should have lone pair, formal charge –1
- etc.
But since you didn’t specify the exact task, here’s the most likely answer:
> Identify the correct Lewis structures or assign formal charges.
All structures except b, c, d, and e are valid or correctly represented.
- b: Incorrect — missing lone pair on carbon.
- c: Incomplete — only two bonds to carbon.
- d: Unusual charge separation — likely invalid.
- e: Incorrect charge — nitrogen should be neutral.
Corrected versions:
- b: CH₃⁻ with lone pair on C
- c: CH₃⁻ with lone pair
- e: CH₃NH₂, neutral
Let me know if the task was different (e.g., identify nucleophiles, electrophiles, resonance, etc.), and I can adjust the explanation.
From what you've included, it appears that these are molecular structures (some with formal charges), and the task likely involves:
- Identifying formal charges
- Determining correct Lewis structures
- Evaluating resonance forms
- Or possibly identifying polarity, acidity/basicity, or hybridization
Let’s go through each one carefully and analyze them step by step based on standard rules of organic chemistry.
---
Step-by-step Analysis of Each Structure
We'll evaluate:
- Formal charge
- Validity of the structure
- Whether it's a reasonable resonance form or ion
---
#### a.
```
H
/
C⁺
/ \
H H
```
- Central carbon has 3 bonds and a +1 formal charge.
- Carbon normally has 4 bonds; here only 3 → electron-deficient.
- This is the methyl cation (CH₃⁺) — a carbocation.
- Valid species, though highly reactive.
- Formal charge: +1 on C
✔ Valid (carbocation)
---
#### b.
```
H
/
C⁻
/ \
H H
```
- Carbon has 3 bonds and a –1 formal charge.
- Total valence electrons: C = 4, 3×H = 3 → total 7 electrons.
- But in this drawing, only 6 electrons shown (3 bonds = 6 e⁻).
- The negative charge implies an extra electron → total 8 electrons, so lone pair should be present.
- But no lone pair shown → incorrect Lewis structure.
✘ Invalid: missing lone pair on carbon.
Correct version would have a lone pair:
```
H
/
C⁻
/ \
H H
```
with two dots on C.
✔ Corrected: methyl anion (CH₃⁻), valid but unstable.
---
#### c.
```
H
/
C⁻
/
H
```
- Only two bonds shown → only 2 bonds to C.
- But carbon has 4 valence electrons.
- With –1 charge, it has 5 electrons.
- Needs two more bonds or lone pairs.
- As drawn: only 2 bonds → only 4 electrons shared → incomplete octet.
✘ Invalid: incomplete structure.
Should be CH₃⁻ (same as b) or maybe a carbanion with lone pair and two H’s.
Possibly typo? Should be same as b?
---
#### d.
```
D⁻—O⁺=O
```
- D = deuterium (²H), isotopic hydrogen.
- O⁺=O: oxygen with +1 charge double-bonded to another oxygen?
- This looks like peroxide-like, but unusual.
- Left oxygen: bonded to D⁻ and double bond to O⁺ → 3 bonds.
- Right oxygen: double bond to left O, and +1 charge → only 2 electrons in bonds, but needs 8.
Wait — let's count:
- Left O: bonded to D⁻ (single), and double bond to O → 3 bonds = 6 electrons.
- Plus negative charge on D, positive on right O.
But D⁻ is deuteride ion, which is rare.
This might represent deuterium oxide with charge separation? But not stable.
Alternatively, could be D–O–O⁺ with resonance?
But D–O–O⁺ doesn’t make sense unless it's a radical or something.
More likely: misdrawn peroxide ion.
Standard peroxide: O–O²⁻
Here: D⁻–O⁺=O → suggests D–O–O, with charges.
But O⁺=O is like ozone or superoxide?
Wait — perhaps it's D–O–O⁺, but O⁺ is unusual.
Actually, this may be a resonance form of hydroperoxide?
But D⁻–O–O⁺ is not favorable due to charge separation.
Also, D⁻ is very strong base — unlikely.
✘ Unlikely to be stable or correct.
Possible misrepresentation.
---
#### e.
```
H₃C–N⁻–H
|
H
```
- Methylamine with negative charge on nitrogen.
- Nitrogen has three bonds (to C, H, H) and a –1 charge → must have lone pair.
- Valence: N has 5 electrons; 3 bonds = 6 e⁻ shared, plus 2 lone pair e⁻ → total 8.
- Charge: 5 valence - (3 bonds + 1 lone pair = 4 electrons assigned) → formal charge = 5 - (3 + 2) = 0? Wait.
Wait: Formal charge formula:
> FC = valence e⁻ - (number of bonds + number of lone pair e⁻)
Better:
> FC = V - (L + B)
Where:
- V = valence electrons
- L = lone pair electrons
- B = number of bonds (each bond counts as 1)
For N:
- V = 5
- Bonds: 3 (to C, H, H)
- Lone pair: 2 electrons → L = 2
- So FC = 5 - (2 + 3) = 0
But here it shows N⁻, so charge is –1.
So if N has three bonds and a lone pair, FC = 0.
To get –1, N must have four lone pair electrons → two lone pairs, and only two bonds.
But here it has three bonds → so cannot have –1 charge unless it's a different structure.
Wait — structure is:
```
H₃C–N⁻–H
|
H
```
That’s three bonds to N: C, H, H → 3 bonds → 6 bonding electrons.
And negative charge → so total electrons around N = 8 → so one lone pair.
Then formal charge = 5 - (1 lone pair × 2 + 3 bonds) = 5 - (2 + 3) = 0
But it shows N⁻, so charge is incorrectly labeled.
✔ Actually, this is methylamine (CH₃NH₂), neutral.
✘ So N⁻ is wrong — should be neutral.
Unless it's methanamine anion, but then N would need four bonds or more.
No — impossible for neutral N with three bonds and –1 charge.
Thus, this structure is invalid.
Correct: CH₃NH₂, neutral.
So e is incorrect.
---
#### f.
```
H₃C–N–H
|
H
```
- Same as e, but no charge.
- This is methylamine (CH₃NH₂).
- Nitrogen has three bonds and a lone pair → neutral.
- ✔ Valid and common molecule.
---
#### g.
```
H₃C–O–CH₃
```
- Dimethyl ether.
- Oxygen has two single bonds to CH₃ groups.
- Oxygen has two lone pairs.
- Neutral molecule.
- ✔ Valid.
---
#### h.
```
CH₃
|
CH₃–P–CH₃
```
- Trimethylphosphine (P(CH₃)₃).
- Phosphorus has three bonds, and one lone pair.
- P valence = 5 → 3 bonds = 3 e⁻ used, lone pair = 2 e⁻ → total 5 → neutral.
- ✔ Valid.
Note: P can expand octet, but here it's fine.
---
#### i.
```
H₃C–S–CH₃
```
- Dimethyl sulfide.
- Sulfur has two bonds, two lone pairs.
- S valence = 6 → 2 bonds = 4 e⁻, lone pairs = 4 e⁻ → total 8 → neutral.
- ✔ Valid.
---
#### j.
```
H₃C–C≡N⁺–H
```
- Wait: C≡N⁺–H → nitrogen triple bonded to carbon, and bonded to H, with +1 charge on N?
But nitrogen can't have five bonds.
Structure: H₃C–C≡N–H, with + on N?
But N has:
- Triple bond to C → 3 bonds
- Single bond to H → 1 bond
- Total 4 bonds → 8 electrons → but N only has 5 valence electrons.
So formal charge:
- V = 5
- Bonds = 4 → 4 electrons counted
- Lone pairs? None shown → 0
- FC = 5 - (0 + 4) = +1 → yes, possible.
But is this a real compound?
This is acetonitrile with protonated nitrogen?
But acetonitrile is CH₃–C≡N (neutral).
Protonating nitrile gives [CH₃–C≡N–H]⁺, which is a nitrilium ion.
Yes! This is protonated acetonitrile, or nitrilium ion.
But nitrilium ions are very electrophilic and usually stabilized by resonance.
But yes, possible.
So: CH₃–C≡N⁺–H → nitrilium ion, with positive charge on N.
✔ Valid, though unstable.
---
#### k.
```
H₃C–N=O
```
- Nitrosomethane.
- Nitrogen bonded to CH₃ and double bond to O.
- Nitrogen has 3 valence electrons? No — N has 5.
Structure: CH₃–N=O
- N has two bonds: one single to C, one double to O → 3 bonds → 6 electrons.
- N needs 8 → so must have one lone pair.
Formal charge:
- V = 5
- Bonds = 3 (count as 3)
- Lone pair = 2 electrons → L = 2
- FC = 5 - (2 + 3) = 0
So neutral.
But actual nitrosomethane is CH₃–N=O, and nitrogen is neutral, but oxygen is partially negative, and nitrogen is electrophilic.
Yes, valid.
But note: resonance exists: CH₃–N⁺=O⁻ ↔ CH₃–N=O with formal charges.
So both resonance forms possible.
✔ Valid.
---
#### l.
```
H₃C–C≡N
```
- Acetonitrile.
- Carbon triple bonded to N, single bond to CH₃.
- Terminal carbon (of CN): triple bond to N, single to C → 4 bonds → neutral.
- Nitrogen: triple bond → 3 bonds → needs lone pair → one lone pair → neutral.
- ✔ Valid.
---
#### m.
```
O⁻
/
H₃C–N⁺–O
\
O
```
Wait — structure is:
```
O⁻
/
H₃C–N⁺–O
\
O
```
But written as:
```
H₃C–N⁺–O
\
O
```
and above: O⁻
So likely:
```
O⁻
/
H₃C–N⁺–O
\
O
```
But that's three oxygens attached to N?
Wait — probably meant to be nitromethane:
```
O
║
H₃C–N⁺–O⁻
║
O
```
But here it's shown as:
```
H₃C–N⁺–O
\
O
```
and above: O⁻
Ah — probably meant:
```
O⁻
/
H₃C–N⁺–O
\
O
```
But that’s three oxygen atoms on N → NO₃⁻ like?
Wait — no.
Actually, nitromethane is CH₃–NO₂, with resonance:
```
O⁻
/
CH₃–N⁺=O
\
O
```
or
```
O
║
CH₃–N⁺–O⁻
\
O
```
But here it's shown as:
```
H₃C–N⁺–O
\
O
```
with O⁻ above.
So likely: CH₃–N⁺(O⁻)(=O) → nitromethane, with one O⁻ and one O=O?
Wait — no.
Standard resonance form of nitromethane:
```
O⁻
/
H₃C–N⁺=O
```
But here it's shown with two oxygens bonded to N, and one O⁻, one double bond?
Wait — the drawing is:
```
O⁻
/
H₃C–N⁺–O
\
O
```
So three bonds from N to O? That’s impossible.
Wait — perhaps it's:
```
O⁻
/
H₃C–N⁺=O
```
and the other O is part of the double bond?
But in text, it says:
```
H₃C–N⁺–O
\
O
```
and above: O⁻
So likely misdrawn.
Probably meant to be:
```
O⁻
/
H₃C–N⁺=O
```
Which is one resonance form of nitromethane.
Yes — CH₃NO₂, with N⁺ and O⁻.
✔ Valid resonance form.
---
#### n.
```
H₂C=N⁺=N⁻
```
- Diazo compound: diazomethane.
- H₂C=N⁺=N⁻
- Carbon: two H, double bond to N → 4 bonds → neutral.
- First N: double bond to C, double bond to N → 4 bonds → but N has 5 valence electrons → formal charge?
Calculate:
- N₁ (middle): bonded to C (double), and N (double) → 4 bonds → 4 electrons → FC = 5 - (0 + 4) = +1 → yes.
- N₂ (terminal): double bond to N → 2 bonds → but has –1 charge → so must have two lone pairs.
So: H₂C=N⁺=N⁻
This is diazomethane, CH₂=N₂, which is a known compound.
Yes — valid.
✔ Valid.
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#### o.
```
H₂N–NH₂
```
- Hydrazine.
- Two NH₂ groups linked by N–N bond.
- Each nitrogen has three bonds (two H, one N) and a lone pair.
- Neutral molecule.
- ✔ Valid.
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✔ Summary of Valid/Invalid Structures
| Letter | Structure | Valid? | Comments |
|-------|----------|--------|--------|
| a | CH₃⁺ | ✔ | Methyl cation |
| b | CH₃⁻ | ✘ | Missing lone pair; should be CH₃⁻ with lone pair |
| c | CH₂⁻ | ✘ | Incomplete; should be CH₃⁻ |
| d | D⁻–O⁺=O | ✘ | Unstable charge separation; likely invalid |
| e | CH₃–N⁻–H₂ | ✘ | N has three bonds and –1 charge → formal charge should be 0; incorrect labeling |
| f | CH₃–NH₂ | ✔ | Methylamine |
| g | CH₃–O–CH₃ | ✔ | Dimethyl ether |
| h | P(CH₃)₃ | ✔ | Trimethylphosphine |
| i | CH₃–S–CH₃ | ✔ | Dimethyl sulfide |
| j | CH₃–C≡N⁺–H | ✔ | Nitrilium ion |
| k | CH₃–N=O | ✔ | Nitrosomethane |
| l | CH₃–C≡N | ✔ | Acetonitrile |
| m | CH₃–N⁺(O⁻)=O | ✔ | Resonance form of nitromethane |
| n | H₂C=N⁺=N⁻ | ✔ | Diazomethane |
| o | H₂N–NH₂ | ✔ | Hydrazine |
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Final Answer:
The task was likely to identify which structures are valid (correct Lewis structures), or assign formal charges, or evaluate resonance.
Based on analysis:
- Valid structures: a, f, g, h, i, j, k, l, m, n, o
- Invalid or incorrectly drawn: b, c, d, e
But if the task was to assign formal charges, then:
For example:
- a: C⁺ → formal charge +1
- b: C⁻ → should have lone pair, formal charge –1
- etc.
But since you didn’t specify the exact task, here’s the most likely answer:
> Identify the correct Lewis structures or assign formal charges.
✔ Final Answer:
All structures except b, c, d, and e are valid or correctly represented.
- b: Incorrect — missing lone pair on carbon.
- c: Incomplete — only two bonds to carbon.
- d: Unusual charge separation — likely invalid.
- e: Incorrect charge — nitrogen should be neutral.
Corrected versions:
- b: CH₃⁻ with lone pair on C
- c: CH₃⁻ with lone pair
- e: CH₃NH₂, neutral
Let me know if the task was different (e.g., identify nucleophiles, electrophiles, resonance, etc.), and I can adjust the explanation.
Parent Tip: Review the logic above to help your child master the concept of lewis structure worksheet.