Ochem Questions... Need a little help here please.

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DDSguyLA

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1. can SN2 ever make a carbocation? is it ever possible?

2. What is an exact difference between a "Transition State" and and "intermediate"?

2. so I undrestand that the speed of addition between Cl and Br are different and Br adds alot faster than Cl... But what difference does that make on Markov and Anti markov or does it??

3. Why do internal alkenes or alkynes boil at a higher temp?? (is it because of delocalization)

4. is NO3 an activator or deactivator??

5. In Kaplan it states that on a "Toulene".... a "NO2" adds 63% on the ortho side and 34% on the para side. Why is that??

6. is heat the only way to tell the diff between E1 and SN1??



Thank you guys
 
1. NO, sn2 is one step while one leaves one forms so no carbonation and no rearrangement
 
Is NO3 is on a ring that means 4 things are attached to the N (the three Os and the ring) so it has no lone pairs to donate and is positively charged so it would be deactivator (just by the way I dont think Ive ever seen this though in a question
 
5. In Kaplan it states that on a "Toulene".... a "NO2" adds 63% on the ortho side and 34% on the para side. Why is that??

I think your mixing two things up. Toluene is a CH3 on a ring NO2 on a ring would be Nitrobenzene and direct meta.
About toluene, is is an O/P director. 2 reasons Ortho is favored, one is more complicated but the over-simplistic approach is because there are two ortho positions and one para so ortho is favored.
 
E1 vs SN2
heat is a good indication but remember you will almost always have mixture of both. More likely you will have to identify if it is unimolecular or bimolecular and both sn- and E- will occur for whichever it is.
Hope this helps good luck!
 
Not 100% sure bout number 2 but I think the intermediate would be the compound which is in the transition state. Meaning the transition state refers the the period when it is the intermediate- which cant be isolated. Does this make sense?
 
1. can SN2 ever make a carbocation? is it ever possible? nope...whenever u see carbocation....has to be sn1 or e1

2. What is an exact difference between a "Transition State" and and "intermediate"? intermediate has a finite life span while transtion state cannot be isolated

2. so I undrestand that the speed of addition between Cl and Br are different and Br adds alot faster than Cl... But what difference does that make on Markov and Anti markov or does it?? doesnt make a difference...and i think cl adds quicker than br but im not 100 percent sure

3. Why do internal alkenes or alkynes boil at a higher temp?? (is it because of delocalization) dont know

4. is NO3 an activator or deactivator?? never seen this on a benzene ring before

5. In Kaplan it states that on a "Toulene".... a "NO2" adds 63% on the ortho side and 34% on the para side. Why is that?? two ortho positions and 1 para

6. is heat the only way to tell the diff between E1 and SN1?? dont really know what ur askin here



Thank you guys
.
 
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1. No. SN2 has a penta-coordinate transition state where the incoming nucleophile is making a bond and the leaving group is breaking its bond. The only charge you get here is a polarized bond which is caused by the leaving group pulling away from its carbon, leaving a partial positive on the carbon the incoming nucleophile is attacking.

2. It all depends on how you define these two I would think. A transition state actually does not really have a "time" associated with it. It is never there for a long enough time actually to see it. When you talk about intermediates, you usually think of stuff like "bromonium ions (bromine bridge), or an epoxide intermediate. An intermediate is usually the steps in between the starting material and final product. An epoxide or oxirane is actually a structure that is not a transition state. These two terms sort of go hand in hand as well if you think about it. You usually say, the "transition state intermediate", meaning that the reaction does not sit like that but will go on to form product from this structure.

3. Anti-Mark and Mark just have to do with addition across double or triple bonds. Lets say you have CH3CH=CH2 reacing with HBR. The H will add across the primary carbon of the molecule, leaving the carbocation on the 2 prime or most stable. Then Br- attacks the carbocation. An example of ANTI-MARK is HBR w/ ROOR. This adds the BR to the least stable part of the double bond, placing a dot in the most stable and then H will attack the dot. Also, a double bond reacting with 1. BH3/THF followed by 2. HOOH/OH- is also considered an ANTI-MARK addition. The speed of something reacting and forming a carbocation etc, actually has to do with 1,2 or 1,4 addition and thermodynamic and kinetic controls.

3. I would think internal alkenes and alkynes have higher BP because they are more stable molecules due to inductive effects. ie. CH3CH=CH-CH3. The middle carbons are sp2 hybridized and the outside methyl's are sp3. There is actually a slight dipole here pointing towards the lower energy state sp2 carbons because they are lower in energy and can be considered theoretically as more EN because the e-density of the methyl's will tend to be closer to the sp2 carbon and not the sp3 carbon. Here you have two methyl groups donating e-density towards a lower energy state. As with, CH3CH=CH2, now you only have one methly donating e- density towards that sp2 carbon so this is actually a higher energy molecule and will boil and lower temperatures. Same goes for alkynes.

4. NO2 off a benzene ring is deactivating and meta-directing because the N actually has a full positive charge. If you do out the resonance structures, attacking para or ortho will place the positive charge next to the full + on the N which is bad. Attacking meta will delocalize the + charge so that it never sits on the carbon next to the Nitrogen.

5. The reason for this is because CH3 off benzene=toluene and is activating and para/ortho directing. Now, there is two ortho sites and one para site, so thats where the percentages come into play.

6. Absolutely not. E1 will only occur when you have a strong acid such as H2SO4 or H3PO4 reacting with an alcohol. That is the ONLY time you get an E1 reaction. You can get SN1 with a weak base such as ethanol reacting with a molecule that has a leaving group or you react acids like HBR, HCL with alcohols. These are all SN1 mechanisms that go through a carbocation intermediate. E1 also goes through a carbocation intermediate but the incoming nucleophile sucks so therefore instead of substituting, you get H abstraction from H's located next to the carbocation.

Hope this helps.

1. can SN2 ever make a carbocation? is it ever possible?

2. What is an exact difference between a "Transition State" and and "intermediate"?

2. so I undrestand that the speed of addition between Cl and Br are different and Br adds alot faster than Cl... But what difference does that make on Markov and Anti markov or does it??

3. Why do internal alkenes or alkynes boil at a higher temp?? (is it because of delocalization)

4. is NO3 an activator or deactivator??

5. In Kaplan it states that on a "Toulene".... a "NO2" adds 63% on the ortho side and 34% on the para side. Why is that??

6. is heat the only way to tell the diff between E1 and SN1??



Thank you guys
 
2B.
The speed of reaction actually does affect markov vs anti - Markov when it comes to Br and Cl additions. As previously mentioned, when HBr reacts with with ROOR, you get an anti markov addition. However, when Cl reacts with ROOR, you get the regular markov addition. (Look at the question and solution 90 in ochem in destroyer for an example.)
 
I think your mixing two things up. Toluene is a CH3 on a ring NO2 on a ring would be Nitrobenzene and direct meta.
About toluene, is is an O/P director. 2 reasons Ortho is favored, one is more complicated but the over-simplistic approach is because there are two ortho positions and one para so ortho is favored.
Can you explain why there are two ortho positions and only one para?😕

Ahh, i understand now.
 
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NO3 is deactivating according to kaplan ochem subject test 4.21 (for those who want the question, it just asks is this a) o/p, b)meta, etc.. so i wont put it up)

meta directing with deactivation. i think because the extra oxygen will make all 3 oxygens attached each have a -1 charge, so the big instability makes it deactivating. someone please elaborate because i'm not sure if i full explained it. thanks!
 
NO3 is deactivating according to kaplan ochem subject test 4.21 (for those who want the question, it just asks is this a) o/p, b)meta, etc.. so i wont put it up)

meta directing with deactivation. i think because the extra oxygen will make all 3 oxygens attached each have a -1 charge, so the big instability makes it deactivating. someone please elaborate because i'm not sure if i full explained it. thanks!

Its like I said before, the N will have a positive charge sine it has the 0 groups and the ring attached to it and the positive charge on the ring will make it a deactivating group since it draws electron density from the ring
 
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