Okay, so I need to figure out the correct sequence of reactions to synthesize 2-(tert-butyl)-1-ethoxy-3-nitrobenzene starting from benzene. The options are A, B, C, D. Let me start by breaking down the target molecule. The parent compound here is benzene with three substituents: a tert-butyl group at position 2, an ethoxy group at position 1, and a nitro group at position 3. Wait, no, wait. Let me check the positions again. The formula is 2-(tert-butyl)-1-ethoxy-3-nitrobenzene. So numbering the benzene ring, position 1 is ethoxy, position 2 is tert-butyl, and position 3 is nitro. Wait, but benzene is a six-membered ring. Wait, maybe the positions are 1, 2, 3 in a certain order. Let me visualize the benzene ring. Let's say position 1 is ethoxy (OEt), position 2 is tert-butyl (C(CH3)3), and position 3 is nitro (NO2). But wait, benzene is a planar ring, so substituents can be adjacent or meta. Wait, the positions might be adjacent. Let me see. Alternatively, maybe the substituents are at positions 1, 2, and 3 in a way that makes them all adjacent. But wait, benzene has six positions. Let me think again. The numbering: if the substituents are at 1, 2, and 3, then they are adjacent. Wait, but that would mean substituents at positions 1, 2, and 3 would all be adjacent, but that's not possible because each substituent is on a different carbon. Wait, maybe the substituents are in positions such that they are meta to each other. Hmm, maybe I need to draw the structure. Let's imagine the benzene ring. Let's place the ethoxy group (OEt) at position 1. Then, the tert-butyl group is at position 2, which is adjacent to position 1. Then the nitro group is at position 3, which is adjacent to position 2. Wait, but that would mean the ethoxy is at 1, tert-butyl at 2, nitro at 3. So the substituents are in positions 1, 2, and 3. But in a benzene ring, positions 1, 2, and 3 are all adjacent, forming a trio of adjacent substituents. Wait, but that's possible. However, the target molecule is 2-(tert-butyl)-1-ethoxy-3-nitrobenzene. So the substituents are at positions 1 (OEt), 2 (t-Bu), and 3 (NO2). So the substituents are all adjacent. Wait, but I think that's a possibility. Alternatively, maybe the substituents are arranged such that the ethoxy is at position 1, the tert-butyl at position 2, and nitro at position 3. But in a benzene ring, substituents are arranged in a way that their positions are relative. Wait, perhaps the key here is the order in which the substituents are introduced because the reactions can affect the positions of the substituents through directing effects.

The synthesis of such a compound likely involves multiple substitution reactions. Since benzene is an aromatic ring, the first substitution (like nitration) will direct the next substituents. Let me recall the directing effects. Nitro groups are meta directors, while ethers (like ethoxy) are activating groups, but wait, wait. Wait, the ethoxy group is an activating group because the ethoxy (OEt) is an ortho/para director. However, if the ethoxy group is already present, then the next substitution (like nitration) would be directed by the existing groups. But in this case, the ethoxy group is introduced first? Wait, but in the target molecule, the ethoxy is at position 1, and the tert-butyl is at position 2. Wait, but if we start with benzene and add substituents, the order matters. Let's think step by step.

The target molecule is 2-(tert-butyl)-1-ethoxy-3-nitrobenzene. So, substituents are at positions 1 (ethoxy), 2 (t-Bu), and 3 (nitro). Wait, but that's a bit confusing. Let me number the benzene ring. Let's fix position 1 as the ethoxy group. Then, position 2 (adjacent to position 1) would be the tert-butyl group. Position 3 (which is meta to position 1) would be the nitro group. Wait, but then the nitro group is meta to the ethoxy. But nitration is a meta director. Hmm. Alternatively, maybe the nitro group is introduced after the ethoxy and tert-butyl groups. Let's think about the directing effects.

The synthesis steps likely involve activating the ring in such a way that the substituents can be added in the correct order. Let's consider the possible reactions. The options given involve various reagents: tert-butyl chloride with AlCl3 (Friedel-Crafts alkylation), nitration (HNO3/H2SO4), nitrosation (NaNO2/HCl), sulfonation (SO3/H2SO4), sulfonation again, other reactions like H3O+ and heat, NaOH with EtBr, etc.

Wait, Friedel-Crafts alkylation is used to add alkyl groups to benzene rings. But Friedel-Crafts alkylation is not very effective with strongly activating groups because the ring is already activated. However, the presence of a strong activating group might make the ring more reactive. But wait, nitro groups are deactivating and meta-directing. Ethoxy is activating and ortho/para-directing. So, if we start with benzene and add a nitro group first, it will be meta directing, but then adding ethoxy would be difficult because the nitro group is deactivating. Alternatively, adding ethoxy first (which is activating) and then nitro would be meta directing. But ethoxy is a strong activating group, so maybe the nitro group can be introduced. Let's think.

Alternatively, perhaps the order is: first introduce the ethoxy group, then the tert-butyl group, then the nitro group. But wait, the ethoxy group is an activating group, so it would direct incoming electrophiles to ortho and para positions. Then, the tert-butyl group (from Friedel-Crafts) would be added. But wait, Friedel-Crafts alkylation requires an activating group because the catalyst (AlCl3) coordinates to the alkyl halide, activating the ring for electrophilic substitution. However, once the ring has a deactivating group like nitro or ethoxy, the Friedel-Crafts alkylation might not proceed. Wait, but ethoxy is an activating group. So, if we first add ethoxy (OEt) to benzene, then perform Friedel-Crafts alkylation to add tert-butyl. Then, nitration. But nitration requires a strong activating group. However, after adding ethoxy and tert-butyl, the ring is still activating, so nitration should be possible.

Wait, but the target molecule has three substituents. Let me think about the order of substitution. Let's assume the steps are:

1. Benzene → add ethoxy group (OEt) → becomes activated, directs incoming electrophiles to ortho and para positions.

2. Add tert-butyl group (from Friedel-Crafts) → since the ethoxy is activating, the tert-butyl would add to ortho or para relative to the ethoxy.

3. Then, add nitro group (nitration) → since the ring has two substituents, the nitro group will be directed by the most activating group. But wait, the ethoxy is a strong activating group (O- is ortho/para director), while the tert-butyl is a strong activating alkyl group (alkyl groups are ortho/para directors as well). So, if the ethoxy and tert-butyl are both present, the nitration would be directed by the strongest activating group. Wait, but ethoxy is a strong activating group (O- is more activating than alkyl groups?), but actually, the activating effect of ethoxy (OEt) is stronger than the activating effect of tert-butyl (C(CH3)3). Wait, no, ethoxy is an activating group (O-), while tert-butyl is an activating alkyl group. However, the ethoxy group is more strongly activating than the tert-butyl. So, the nitro group would be added to the most activated positions, which are ortho and para to the ethoxy group. But wait, the tert-butyl is already present. Let's see.

Alternatively, maybe the nitration occurs after adding the tert-butyl group. Let's think about the steps. Let's suppose we start with benzene.

First step: Add ethoxy group (OEt) via Friedel-Crafts alkylation. Wait, no, Friedel-Crafts alkylation uses alkyl halides. To add an ethoxy group (OEt), we would need an ethoxylation. Wait, but Friedel-Crafts alkylation requires an alkyl halide and AlCl3 as a catalyst. To add an ethoxy group, we would need an ethoxyating agent. Wait, maybe using an ethyl chloride with AlCl3. But wait, Friedel-Crafts alkylation adds alkyl groups. Adding an ethoxy group would require an ethoxy group being attached. Wait, perhaps using an ethyl chloride (ethyl bromide) with AlCl3 as a catalyst. So, first step: benzene + ethyl chloride (CH2CH3Cl) in AlCl3 → benzene ethyl ether (OEt) via Friedel-Crafts alkylation. Wait, but Friedel-Crafts alkylation is used to add alkyl groups to benzene rings. The reaction is: benzene + R-X (like CH2CH3Cl) → benzene with R group attached. So, the product would be ethylbenzene. But wait, in that case, the ethyl group is an activating group (alkyl is ortho/para director). Then, the next step would be nitration. Nitration (HNO3/H2SO4) would add a nitro group to the para position relative to the ethyl group. Then, we would have ethyl group at position 1, nitro at position 4. Wait, but the target has ethoxy at position 1, tert-butyl at position 2, and nitro at position 3. Hmm, this seems to not match. Maybe the order is different.

Alternatively, perhaps the first substituent is the tert-butyl group. But the target has ethoxy at position 1. Wait, maybe the steps are as follows:

1. Benzene undergoes Friedel-Crafts alkylation with tert-butyl chloride (C(CH3)3Cl) in AlCl3 → tert-butylbenzene (C6H4-C(CH3)3). The tert-butyl group is an activating group (alkyl), ortho/para director.

2. Then, nitration: HNO3/H2SO4 → adds nitro group. The nitro group is meta to the tert-butyl group. So, if the tert-butyl is at position 1, nitro would be at position 3. Then, the ring has substituents at positions 1 (tert-butyl) and 3 (nitro).

3. Then, add ethoxy group. But ethoxy is an activating group, which would direct incoming electrophiles to ortho and para positions. However, the ring already has a nitro group (deactivating). So, the nitro group is meta-directing. Wait, but the ethoxy group would be added after the nitro group. Wait, but nitration is step 2. So, after step 2, we have tert-butyl at 1 and nitro at 3. Then, to add ethoxy, which is an activating group, would direct to positions ortho and para to the ethoxy. Wait, but the ethoxy is being added, so the positions would be where? Let's see. If we have substituents at 1 (tert-butyl) and 3 (nitro), the ring is deactivating at 3. Adding ethoxy would be difficult because the ring has a nitro group. Alternatively, maybe the ethoxy is added after the nitro group. Wait, but nitration is done after adding the tert-butyl group. Let's think again.

Alternatively, maybe the order is:

1. Benzene → add ethoxy group (using Friedel-Crafts alkylation: ethyl chloride with AlCl3) → ethylbenzene (OEt group at position 1, assuming ethyl is added at position 1).

Wait, no, Friedel-Crafts alkylation adds the R group to the benzene. So, benzene + CH2CH3Cl → ethylbenzene (benzene with ethyl group attached). Then, ethyl group is an activating group (alkyl), so directs incoming electrophiles to ortho and para positions. Then, nitration would add a nitro group to the ortho or para positions relative to the ethyl group. Let's say the nitro group is added at the para position (position 4 relative to ethyl group at position 1). Then, the ring has ethyl at 1, nitro at 4. Then, adding a tert-butyl group would require a Friedel-Crafts alkylation, but the ring has a nitro group (deactivating), so Friedel-Crafts would not proceed. Therefore, that approach might not work. Alternatively, maybe the tert-butyl group is added before the ethoxy group.

Wait, but the target has ethoxy at position 1. Let's think again. Let's try the order: first add the tert-butyl group, then the ethoxy group, then nitro. But how?

Wait, maybe the order is:

1. Benzene → add tert-butyl group (using Friedel-Crafts alkylation with t-butyl chloride and AlCl3) → tert-butylbenzene (C(CH3)3 attached at position 1).

2. Then, add ethoxy group. Since the tert-butyl group is an activating group (alkyl, ortho/para), the ethoxy group would be added to the ortho or para positions relative to the tert-butyl. Let's say we add ethoxy at position 2 (ortho to tert-butyl) and position 4 (para). But the target has ethoxy at position 1. Wait, maybe the numbering is different. Wait, perhaps the initial numbering is different. Let me clarify.

Alternatively, perhaps the first substituent is the ethoxy group, which is added first. Let's see:

1. Benzene → add ethoxy group (using Friedel-Crafts alkylation: ethyl chloride with AlCl3) → ethylbenzene (OEt group at position 1).

2. Then, add tert-butyl group. The ethoxy group is activating (O-), so the tert-butyl would be added to ortho or para positions relative to the ethoxy. Suppose we add tert-butyl at position 2 (ortho to ethoxy). Then, the ring has ethoxy at 1 and tert-butyl at 2. Then, nitration would be directed by the ethoxy group (activating, ortho/para). The nitro group would be added to position 3 (para to ethoxy and adjacent to tert-butyl). Wait, but the target has nitro at position 3. Let's see:

After steps 1 and 2: ethoxy at 1, tert-butyl at 2. Then, nitration would add nitro at position 3 (para to ethoxy). That would match the target molecule. So the substituents would be ethoxy (1), tert-butyl (2), and nitro (3). But wait, the target is 2-(tert-butyl)-1-ethoxy-3-nitrobenzene. So nitro is at position 3. But in the numbering, position 3 would be meta to position 1 (ethoxy) and adjacent to position 2 (tert-butyl). Wait, but if ethoxy is at 1, tert-butyl at 2, nitro at 3, then the substituents are all adjacent. But how does the directing work here?

Wait, after adding ethoxy and tert-butyl, the ring has two substituents: ethoxy (OEt) at 1, tert-butyl (C(CH3)3) at 2. The ethoxy is activating (O-), so the nitration would be directed to ortho or para positions relative to ethoxy. The para position relative to ethoxy would be position 4 (if ethoxy is at 1, positions are 1 (OEt), 2 (C(CH3)3), 3, 4 (para to OEt), 5, 6). But the nitro is at position 3, which is adjacent to ethoxy (1) and tert-butyl (2). So the nitro would be ortho to ethoxy (position 3 is ortho to position 1's ethoxy? Wait, no. Wait, benzene is a ring. Position 1 is ethoxy, position 2 is tert-butyl. Then, position 3 is adjacent to both. But ethoxy is at 1, which is activating. So nitration would be directed to ortho (position 2) or para (position 4) relative to ethoxy. However, position 2 is already occupied by the tert-butyl group, so nitration would go to position 4. But the target has nitro at position 3. That's a problem. So this approach would place nitro at position 4, not 3. Therefore, this order (add ethoxy first, then tert-butyl) would not lead to nitro at position 3. Hmm. So maybe the order is different. Let's try another approach.

Alternatively, maybe the nitro group is added first. Let's see:

1. Nitration of benzene → nitro group at position 1. Then, add ethoxy (OEt) group. The nitro group is deactivating (meta director), so the ethoxy group would be added to the meta position relative to nitro (position 3). Then, add tert-butyl group. The ring now has nitro at 1 and ethoxy at 3. The ethoxy group is activating (O-), so the tert-butyl would be added to ortho or para relative to ethoxy. The para position relative to ethoxy (position 6) would be available. But the target has tert-butyl at position 2. Wait, but position 2 is adjacent to position 1 (nitro). So that might not align. Alternatively, if the ethoxy is at position 3, then the tert-butyl could be added at position 2 (ortho to ethoxy). Then, the ring would have nitro at 1, ethoxy at 3, and tert-butyl at 2. But that would give substituents at positions 1, 2, and 3. Wait, but the target is 2-(tert-butyl)-1-ethoxy-3-nitrobenzene. So nitro is at position 3. Wait, no, the target's numbering is such that the substituents are 1-ethoxy, 2-tert-butyl, 3-nitro. So maybe the initial nitration is at position 3, but that would require the nitro being added first. Let me think again.

Alternatively, perhaps the steps are:

1. Benzene → add ethoxy group (OEt) via Friedel-Crafts alkylation → ethylbenzene.

2. Then, nitrate to add nitro group. Nitration is directed by the ethoxy group (activating, ortho/para). The nitro group would be added at position 4 (para to ethoxy) or position 2 (ortho to ethoxy). Let's say we add nitro at position 2. Then, the ring has ethoxy at 1 and nitro at 2. Then, add tert-butyl group. The ethoxy is activating, so tert-butyl would be added to ortho or para positions relative to ethoxy. Para to ethoxy is position 4, ortho is position 2 (occupied by nitro). So tert-butyl would be added at position 4. But the target has tert-butyl at position 2. So this approach doesn't work. Alternatively, maybe nitration is done after adding the tert-butyl group. Let's try:

1. Benzene → add tert-butyl group (using Friedel-Crafts alkylation) → tert-butylbenzene.

2. Then, add ethoxy group. The tert-butyl is an activating group (alkyl), so ethoxy would be added to ortho or para positions relative to tert-butyl. Let's say we add ethoxy at position 2 (ortho to tert-butyl) and position 4 (para). If we add ethoxy at position 2, then the ring has tert-butyl at 1 and ethoxy at 2. Then, nitration would be directed by the ethoxy group (activating, ortho/para). The nitro group would be added at position 3 (ortho to ethoxy) or position 5 (para to ethoxy). But the target has nitro at position 3. So, adding nitro at position 3 would give substituents at 1 (tert-butyl), 2 (ethoxy), 3 (nitro). But wait, the target is 2-(tert-butyl)-1-ethoxy-3-nitrobenzene. So the substituents are at positions 1 (ethoxy), 2 (tert-butyl), 3 (nitro). But in this case, the substituents are at positions 1 (OEt), 2 (C(CH3)3), 3 (NO2). So, the order would be ethoxy first, then tert-butyl, then nitro. Wait, but how does that work?

Wait, after adding ethoxy (position 1), then adding tert-butyl (position 2), then nitration would be directed by the ethoxy group (activating, ortho/para). The para position relative to ethoxy is position 4. So nitro would be added at position 4, not 3. But the target has nitro at position 3. So that approach doesn't work. Alternatively, perhaps the nitration is done before adding the ethoxy. Let me try that.

1. Benzene → add tert-butyl group (using Friedel-Crafts alkylation) → tert-butylbenzene.

2. Nitrate to add nitro group. The tert-butyl is activating (alkyl), so nitro would be added to ortho or para positions. Let's say nitro is added at position 4 (para to tert-butyl). Then, the ring has tert-butyl at 1 and nitro at 4. Then, add ethoxy group. The nitro group is deactivating and meta-directing, so ethoxy would be added to meta positions relative to nitro. The meta positions relative to nitro (position 4) would be positions 2 and 6. Let's choose position 2. Then, the ring has tert-butyl at 1, nitro at 4, ethoxy at 2. But the target has ethoxy at 1, so this approach doesn't match.

This is getting complicated. Maybe I need to look at the answer choices and see which steps correspond to the correct sequence.

Looking at the options:

Option A:

i) tert-butyl chloride/AlCl3 → Friedel-Crafts alkylation adds tert-butyl group.

ii) HNO3/H2SO4 → nitration.

iii) Fe/HCl (probably reduction of nitro group to amine? But that's a reduction step, not sure if needed here.)

iv) HNO3/H2SO4 → another nitration? Not sure why.

v) NaNO2/HCl → this is a diazotization step, typically for introducing amino groups. But the target doesn't have an amino group. So maybe this is part of a substitution.

vi) H3O+ and H2O/Heat → acid hydrolysis? Or something else.

vii) NaOH/EtBr → perhaps an alkylation or substitution.

viii) SO3/H2SO4 → sulfonation, adding a sulfonic acid group.

ix) dilute H2SO4 → another acid workup.

Option B:

i) HNO3/H2SO4 → nitration first.

But benzene is not activated yet, so nitration might not proceed. Unless benzene is activated by substituents. But without any substituents, nitration of benzene is possible but requires a catalyst. However, Friedel-Crafts requires an activating group. So if we start with nitration, benzene is not activated, so nitration might not proceed. Therefore, option B's first step is nitration, which might not be feasible. Unless it's nitration after some activation. But without any substituent, nitration of benzene would produce a mixture of products (with different substitution patterns), but it's possible. However, for high-yield synthesis, likely the substituent is needed first.

Option C:

i) tert-butyl chloride/AlCl3 → add tert-butyl group.

ii) SO3/H2SO4 → sulfonation. But the target doesn't have a sulfonic acid group. So perhaps this is introducing a nitro group. Wait, no, the target has nitro. Wait, the target has nitro, so perhaps this is a sulfonation step. But the target doesn't have a sulfonic acid group. Hmm, maybe not.

Option D:

i) tert-butyl chloride/AlCl3 → add tert-butyl.

ii) HNO3/H2SO4 → nitration.

iii) SO3/H2SO4 → sulfonation.

iv) NaNO2/HCl → diazotization.

v) dilute H2SO4 → acid workup.

vi) H3O+ and H2O/Heat → another workup.

vii) NaOH/EtBr → substitution.

viii) Fe/HCl → reduction.

ix) HNO3/H2SO4 → another nitration.

This seems to add a sulfonic acid group and then a nitro group, which doesn't match the target. The target only has nitro, ethoxy, and tert-butyl groups. So options with SO3/H2SO4 (sulfonation) steps might be introducing a sulfonic acid group, which isn't present in the target. Therefore, options with step ii) using HNO3/H2SO4 and step iii) using SO3/H2SO4 might not be the right path since the target only has nitro. Unless the SO3/H2SO4 is for sulfonation, but the target doesn't require that. Therefore, options C and D have steps introducing sulfonic acid groups, which are not in the target. So perhaps the correct option is A or B.

Wait, the target doesn't have a sulfonic acid group, so any options with SO3/H2SO4 steps (like C and D) might be incorrect. Therefore, the correct answer is likely between A and B.

Option B's steps:

i) HNO3/H2SO4 → nitrate benzene.

But without any activating groups, nitration of benzene is possible but requires a catalyst. However, the presence of a nitro group might be added, but then subsequent steps might not fit the target. Let's think. If we start with benzene and nitrate it first, we get nitrobenzene. Then, step ii) Fe/HCl → which is a reduction step. Nitro groups can be reduced to amino groups. But the target doesn't have an amino group. Then, step iii) HNO3/H2SO4 → another nitration. But the ring now has a nitro group (reduced from nitro?), but this seems confusing. Alternatively, step iii) is sulfonation. Wait, but the target doesn't have a sulfonic acid group. So this seems unlikely.

Option A's steps:

i) tert-butyl chloride/AlCl3 → add tert-butyl.

ii) HNO3/H2SO4 → nitration. The tert-butyl is activating, so nitro would be added ortho or para to tert-butyl.

Assuming nitro is added para to tert-butyl (position 4), then step iii) Fe/HCl → reduction of nitro to amine. But the target doesn't have an amine. Then step iv) HNO3/H2SO4 → another nitration. But the ring now has a nitro group (which is meta director), so nitration would go meta to nitro. But the target has nitro in a specific position. This seems convoluted and might not lead to the correct product.

Alternatively, perhaps the steps after adding the tert-butyl group don't involve nitration again. Let me check the steps in option A:

After step ii) nitration, the ring has tert-butyl and nitro groups. Then step iii) Fe/HCl → reduces nitro to amine. Then step iv) another nitration. Then step v) NaNO2/HCl → which is diazotization. Then step vi) H3O+/H2O/Heat → hydrolysis. Then step vii) NaOH/EtBr → perhaps substitution. Then step viii) SO3/H2SO4 → sulfonation. Then step ix) H2SO4 → workup.

This seems like a lot of steps and might not align with the target structure. The target only has three substituents: ethoxy, tert-butyl, and nitro. The steps in option A introduce several more steps that might complicate the structure.

Option B's steps:

i) HNO3/H2SO4 → nitrate benzene. Then step ii) Fe/HCl → reduce nitro to amine. Then step iii) HNO3/H2SO4 → nitrate again. Then step iv) NaNO2/HCl → diazotization. Then step v) dilute H2SO4 → acid workup. Then step vi) H3O+/H2O/Heat → maybe hydrolysis. Then step vii) NaOH/EtBr → substitution. Then step viii) SO3/H2SO4 → sulfonation. Then step ix) H2SO4 → workup.

Again, this seems to add more groups than the target. The target has three substituents, but these steps add multiple groups. So perhaps the correct answer is A or B, but the steps need to be carefully analyzed.

Alternatively, perhaps the correct order is to add ethoxy first, then nitrate, then add tert-butyl. But let's see.

Wait, let's think again. The target has ethoxy at position 1, tert-butyl at 2, nitro at 3. So the substituents are all adjacent to each other. Let's consider the directing effects:

- Ethoxy (OEt) is activating, ortho/para director.

- Tert-butyl is activating, ortho/para director.

- Nitro is deactivating, meta director.

If we start with ethoxy, then add tert-butyl (ortho/para to ethoxy), then nitrate. The nitro group would be directed by the most activating group, which would be the ethoxy. But after adding tert-butyl, the ring has two substituents: ethoxy and tert-butyl. The most activating is ethoxy, so nitration would be directed by ethoxy. But ethoxy is at position 1, so nitration would be at position 3 (para to ethoxy) or position 2 (ortho to ethoxy). However, the tert-butyl is at position 2. If the nitro is added at position 3 (para to ethoxy), then the substituents would be ethoxy (1), tert-butyl (2), nitro (3). Which matches the target. So the order would be:

1. Add ethoxy via Friedel-Crafts: benzene → ethylbenzene.

2. Add tert-butyl via Friedel-Crafts: ethylbenzene → ethyl-C(CH3)3 benzene.

3. Nitrate: directed by ethoxy (activating), so nitro at position 3 (para to ethoxy). Then, the substituents are ethoxy (1), tert-butyl (2), nitro (3). Which matches the target.

But wait, Friedel-Crafts alkylation requires an activating group. Ethyl group is activating, so Friedel-Crafts works. After adding ethoxy (position 1), adding tert-butyl group (position 2) via Friedel-Crafts alkylation: but the ethoxy is activating, so the tert-butyl would be added to ortho or para relative to ethoxy. However, the target requires tert-butyl at position 2 (ortho to ethoxy). So this would work. Then, nitration would be directed by ethoxy (activating) to position 3 (para to ethoxy). So the substituents would be ethoxy (1), tert-butyl (2), nitro (3). Which is the target. So the order of steps would be:

- Add ethoxy first, then tert-butyl, then nitro. But how does this translate into the answer choices? Let's look at the options.

Looking at the answer choices, none of them seem to directly correspond to this sequence. Let me check the steps in the options.

Option A:

i) tert-butyl chloride/AlCl3 → add tert-butyl first. Then nitration, then Fe/HCl, etc. Doesn't fit.

Option B:

i) HNO3/H2SO4 → nitrate first. Then Fe/HCl, etc. Doesn't fit.

Option C:

i) tert-butyl chloride/AlCl3 → add tert-butyl first. Then SO3/H2SO4 → sulfonation. Then HNO3/H2SO4 → nitration. Then NaNO2/HCl → diazotization. Then dilute H2SO4. Then H3O+/H2O/Heat. Then NaOH/EtBr → substitution. Then SO3/H2SO4. Then dilute H2SO4. This seems to involve multiple steps that don't match the target.

Option D:

i) tert-butyl chloride/AlCl3 → add tert-butyl. Then HNO3/H2SO4 → nitration. Then SO3/H2SO4 → sulfonation. Then NaNO2/HCl → diazotization. Then dilute H2SO4. Then H3O+/H2O/Heat. Then NaOH/EtBr → substitution. Then Fe/HCl → reduction. Then HNO3/H2SO4 → another nitration. This seems to add more groups than needed.

Wait, but the target only requires three substituents. So perhaps the steps in the answer choices are more about the correct sequence of steps, even if some steps are redundant or involve other groups. But in the target, there's no sulfonic acid group or amino group. Therefore, the answer must be a sequence that ends with nitro and the other two groups without introducing any extra groups.

Looking back at the target: 2-(tert-butyl)-1-ethoxy-3-nitrobenzene. So substituents are ethoxy (OEt), tert-butyl (C(CH3)3), and nitro (NO2). The order in which they are added must be such that the directing effects are correct.

The correct order would be:

1. Add ethoxy (OEt) group → activating, ortho/para director.

2. Add tert-butyl group (C(CH3)3) → activating, ortho/para director. Since the ethoxy is at position 1, tert-butyl would be added at position 2 (ortho to ethoxy).

3. Nitrate → directed by the most activating group, which is ethoxy. Since ethoxy is at 1, nitration would be at position 3 (para to ethoxy). Then, the substituents are ethoxy (1), tert-butyl (2), nitro (3). Which matches the target.

But in the answer choices, Friedel-Crafts alkylation is used with tert-butyl chloride and AlCl3 (step i) in option A. Then nitration (step ii). Then other steps. But according to the correct sequence, the ethoxy should be added first. However, Friedel-Crafts alkylation requires an activating group to work. Ethyl group (from ethoxy) is activating, so Friedel-Crafts works. But if we add ethoxy first, then add tert-butyl via Friedel-Crafts, which is possible because ethoxy is activating. Then nitrate. But in the answer choices, Friedel-Crafts steps are first with tert-butyl. So perhaps the answer is option A, which starts with adding tert-butyl first, then ethoxy, then nitration. But let's see.

Wait, in the correct sequence, we need to add ethoxy first, then tert-butyl, then nitration. But in option A, the first step is adding tert-butyl. Then nitration. Then Fe/HCl (reduction). Then more steps. After nitration, we have tert-butyl and nitro groups. Then, Fe/HCl would reduce nitro to amine. Then step iv) HNO3/H2SO4 → another nitration. Then step v) NaNO2/HCl → diazotization. Then step vi) hydrolysis. Then step vii) substitution. Then step viii) sulfonation. Then step ix) workup. This seems too lengthy and adds multiple groups. Therefore, perhaps the correct answer is not among the options, but since we have to choose, perhaps option A is the correct one, but with the understanding that the steps after nitration are not required. Alternatively, perhaps I'm missing something.

Alternatively, perhaps the steps after nitration are for removing any unwanted functional groups. For example, after nitration, Fe/HCl could reduce nitro to amine. But the target doesn't have an amine. Then nitration again would add another nitro. But the target only has one nitro group. Therefore, option A's steps might not be correct.

Alternatively, perhaps the correct answer is option B, which starts with nitration. If benzene is first nitrated to nitrobenzene, then Friedel-Crafts alkylation with tert-butyl chloride would add tert-butyl group (since nitro is deactivating, but Friedel-Crafts requires an activating group). Wait, that's a problem. Nitro is deactivating, so Friedel-Crafts alkylation won't work. Therefore, option B is invalid.

Therefore, if we can't start with nitration, the correct sequence must be to add ethoxy first. Then add tert-butyl. Then nitrate. However, the answer choices don't have a sequence that starts with ethoxy. Therefore, perhaps the answer is option A, which uses Friedel-Crafts to add tert-butyl first, then ethoxy, then nitration. Then, steps to reduce nitro to amine (step iii) Fe/HCl), but the target doesn't have an amine. However, if after nitration, the nitro group is reduced to amine, and then further steps are done, perhaps this leads to the correct product. But then, the subsequent steps would add more groups, which is not the case in the target. Therefore, this seems unlikely.

Alternatively, perhaps the correct answer is option A, but the steps after nitration are not necessary. For example, after step ii) nitration, the ring has tert-butyl and nitro groups. Then step iii) reduces nitro to amine. Then step iv) nitrate again. But the target only has one nitro group. Therefore, this can't be.

Alternatively, perhaps the answer is option B. Let's reevaluate option B:

i) HNO3/H2SO4 → nitrate benzene. But benzene is deactivated; nitration might not proceed. However, if there's already an activating group, but benzene has none. So nitration of benzene is possible but requires a catalyst. Once nitro is added, then step ii) Fe/HCl → reduce nitro to amine. Then step iii) nitrate again. But the target has only one nitro group. So this seems to produce more than needed.

Alternatively, perhaps the correct answer is option A, but the steps after nitration are for some other purpose. For example, after nitration, they reduce the nitro group to amine (step iii), then perform another nitration (step iv), which would add another nitro group. But the target only has one nitro. Therefore, this seems incorrect.

Alternatively, perhaps the steps after nitration are to do something else. For example, perhaps step iv) HNO3/H2SO4 is to nitrate again, but why? The target has only one nitro group. So this seems off.

Alternatively, perhaps the steps after nitration are to remove the nitro group. For example, step iii) NaNO2/HCl → diazotization, step iv) H3O+ → hydrolysis (maybe converting diazonium to something else). But the target doesn't have a diazonium group. However, the target has a nitro group, so perhaps these steps are to convert the nitro group to something else. For example, diazotization followed by hydrolysis could convert nitro to something else, but the target still has nitro. Therefore, this seems unlikely.

Given all this confusion, perhaps the correct answer is option A, but I'm not entirely sure. Alternatively, perhaps the correct answer is option B, but I can't see how.

Wait, another approach: Let's look for the correct order of substituents. The target has ethoxy at position 1, tert-butyl at 2, nitro at 3. Let's consider the order of adding substituents:

1. Add ethoxy first (OEt).

2. Then add tert-butyl (C(CH3)3) ortho to ethoxy.

3. Then nitrate.

But in this case, the nitration would be directed by the ethoxy group, which is activating, so nitro would be added para to ethoxy, which is position 4. But the target has nitro at position 3. Therefore, this approach doesn't work.

Alternatively, perhaps the correct order is:

1. Add ethoxy first.

2. Nitrate → nitro added at position 3 (para to ethoxy).

3. Then add tert-butyl → but where? Since the ring now has ethoxy at 1 and nitro at 3. The ethoxy is activating (ortho/para), so tert-butyl would be added at position 2 (ortho to ethoxy). Then, the substituents would be ethoxy (1), tert-butyl (2), nitro (3). Which matches the target. So the order would be: ethoxy → nitration → tert-butyl.

But in the answer choices, Friedel-Crafts steps are used with tert-butyl chloride first. So the correct sequence would involve adding ethoxy first, then nitration, then tert-butyl. However, none of the options follow this order. Let's check the options again.

Option A:

i) tert-butyl chloride/AlCl3 → add tert-butyl.

ii) HNO3/H2SO4 → nitrate.

iii) Fe/HCl → reduce nitro to amine.

iv) HNO3/H2SO4 → nitrate again.

v) NaNO2/HCl → diazotization.

vi) H3O+/H2O/Heat → hydrolysis.

vii) NaOH/EtBr → substitution.

viii) SO3/H2SO4 → sulfonation.

ix) H2SO4 → workup.

This seems to introduce multiple groups, which the target doesn't have. Therefore, option A is incorrect.

Option B:

i) HNO3/H2SO4 → nitrate.

But benzene is not activated, so nitration would occur at a specific position. If nitrated first, then Friedel-Crafts would not work for the next steps. Therefore, option B is unlikely.

Given all this, perhaps the correct answer is option A, but the steps after nitration are not necessary. However, since the answer must be one of the options, and considering the steps in option A, perhaps the correct answer is A.
</think>