Just want to make sure that my thought process is right on this one.

5 compounds:

n-butyl chloride
n-butyl bromide
sec-butyl chloride
tert-butyl chloride
and crotyl chloride

Each is reacted with NaI (SN2?) and AgNO3 (SN1?)

And we have to rank the reaction time and wether we think a reaction would occur or not.

So SN1 is allyl > tert > sec> primary>>methyl
by carbocation stability. So I think crotyl chloride is considered an allyl by the double bond in structure so fastest to slowest would be: crotyl> tert-butyl chloride> sec-butyl chloride> n-butyl bromide> n-butyl chloride (slowest because Br is better leaving group?)
As far as reaction goes, I don't think primary can go SN1, so the last two would be no reaction

As for SN2 NaI it's ranked by hinderance so
crotyl?>n-butyl chloride>n-butyl bromide> sec. > tert.
And I know tert. can't go SN2 so no reaction for that one.

Your thought process is mostly correct. Here's a step-by-step breakdown:

1. Ranking the compounds by reaction time for SN1 (using carbocation stability):
- The stability of carbocations follows the order: allyl > tertiary > secondary > primary > methyl.
- Crotyl chloride has an allylic carbocation and would be the fastest to react via SN1.
- The order from fastest to slowest would be: crotyl chloride > tert-butyl chloride > sec-butyl chloride > n-butyl bromide > n-butyl chloride.

2. Considering the possibility of SN1 reactions:
- SN1 reactions can occur for compounds that can form stable carbocations.
- Crotyl chloride has the potential for an SN1 reaction due to the allylic carbocation.
- Tert-butyl chloride and sec-butyl chloride may undergo an SN1 reaction due to the presence of a tertiary carbon, albeit slower compared to crotyl chloride.
- N-butyl bromide may react via SN1, but it would be slower than the previous compounds due to bromide being a poorer leaving group than chloride.
- It is less likely for n-butyl chloride to undergo an SN1 reaction because it lacks a stabilizing factor like allylic or tertiary carbocation formation. So a reaction rate is expected to be slow or negligible.

3. Ranking the compounds by reaction time for SN2 (using hinderance):
- Hinderance refers to the steric hindrance or crowding around the carbon atom undergoing nucleophilic substitution.
- For SN2 reactions, less hindered substrates are faster.
- The order from fastest to slowest would be: crotyl chloride > n-butyl chloride > n-butyl bromide > sec-butyl chloride > tert-butyl chloride.

4. Considering the possibility of SN2 reactions:
- SN2 reactions occur for compounds that are not hindered or less hindered.
- Crotyl chloride, n-butyl chloride, and n-butyl bromide have potential for SN2 reactions.
- Sec-butyl chloride has slightly more hinderance around the carbon, making it less favorable for SN2.
- Tert-butyl chloride is highly hindered and cannot undergo SN2.

To summarize:
- Crotyl chloride is likely to undergo both SN1 and SN2 reactions, with faster rates.
- Tert-butyl chloride cannot undergo either SN1 or SN2 reactions.
- Sec-butyl chloride might undergo an SN1 reaction but is less favorable for SN2.
- N-butyl bromide may undergo an SN1 reaction but is slower than the previous compounds.
- N-butyl chloride is slower than n-butyl bromide for SN1 and may not undergo SN2.

Your thought process is generally correct, but there are a few adjustments that need to be made.

First, let's start with the reactions with NaI. The SN2 reaction occurs with a strong nucleophile, like iodide ion (I-), and the rate of the reaction is determined by the steric hindrance around the carbon atom undergoing substitution.

Based on the structure and steric hindrance, the ranking for the SN2 reaction is as follows, from fastest to slowest:

n-butyl bromide > n-butyl chloride > sec-butyl chloride > crotyl chloride > tert-butyl chloride

This means that the reaction with n-butyl bromide will be the fastest, followed by n-butyl chloride, sec-butyl chloride, crotyl chloride, and tert-butyl chloride. So your ranking for the SN2 reaction is correct.

However, you mentioned crotyl chloride as a possible allyl chloride. Allyl chloride would have a double bond directly attached to the carbon undergoing substitution. In the case of crotyl chloride, the double bond is one carbon away from the carbon undergoing substitution, so it is not considered an allyl chloride. It should be listed as crotyl chloride.

Now let's move on to the reactions with AgNO3. The SN1 reaction occurs with a weak nucleophile and a good leaving group, like Ag+ and NO3-. The rate of the reaction is determined by the stability of the carbocation intermediate formed.

Based on carbocation stability, the ranking for the SN1 reaction is as follows, from fastest to slowest:

tert-butyl chloride > sec-butyl chloride > n-butyl bromide > n-butyl chloride.

So your ranking for the SN1 reaction is correct.

However, you mentioned crotyl chloride as a possibility for the SN1 reaction. Crotyl chloride, being an alkyl halide with a primary carbon, is not likely to undergo SN1 reaction. The stability of the carbocation intermediate formed is an important factor, and primary carbocations are highly unstable. Therefore, crotyl chloride should not be considered for the SN1 reaction, and your conclusion about the last two compounds not undergoing SN1 reaction is correct.

To summarize:

SN2 reaction rankings: n-butyl bromide > n-butyl chloride > sec-butyl chloride > crotyl chloride > tert-butyl chloride
SN1 reaction rankings: tert-butyl chloride > sec-butyl chloride > n-butyl bromide > n-butyl chloride

Reactions with NaI:
- n-butyl bromide: SN2 reaction is expected and the fastest
- n-butyl chloride: SN2 reaction is expected, but slower compared to n-butyl bromide
- sec-butyl chloride: SN2 reaction is expected, but slower compared to n-butyl chloride
- crotyl chloride: SN2 reaction is expected, but slower compared to sec-butyl chloride
- tert-butyl chloride: No SN2 reaction is expected due to severe steric hindrance.

Reactions with AgNO3:
- tert-butyl chloride: SN1 reaction is expected and the fastest
- sec-butyl chloride: SN1 reaction is expected, but slower compared to tert-butyl chloride
- n-butyl bromide: SN1 reaction is expected, but slower compared to sec-butyl chloride
- n-butyl chloride: SN1 reaction is expected, but slower compared to n-butyl bromide
- crotyl chloride: No SN1 reaction is expected due to the instability of primary carbocations.