[OrgoloathesJess]

Okay, I decided it would be best if I started a new topic for these questions since they have nothing to do with mechanism sources. I hope you all think it is a good idea and don't have a problem with the new thread. I have some questions for one of my problems:

The following cyclic polyene undergoes an ozononolysis reaction at room temperature. Draw the structure of the intermediate formed after the first step. Draw the structure of all organic products formed from the reaction. Indicate products as major, minor, or equal amount.

[OrgoloathesJess]

I have one question on this one:
A simple and inexpensive way to prepare alkenes is by heating alcohols in acidic solutions. This reaction is prone to rearrangements and often gives unexpected products. For example, the reaction of the following five member ring produces a major product that is a six member ring. Write the complete mechanism involved in the formation of both product. Indicate why each product is the major product and the minor product.

My Answers, work, and questions:
This is an example of acid catalyzed dehydration of alcohols mechanism. right? (the first attachment is the mechanism given with the question.)
FYI: I have yet to indicate the reason behind the minor and major labeling on my scratch work. I think it has to do with the number of alkyl groups attached to the double bonds. The minor compound only has one alkyl group versus the major compound with two alkyl groups.

Also if you have trouble reading my hand writing and have any suggestions to make my questions and work easier to read for you guys please don't hesitate to let me know.

[OrgoloathesJess]

I found a problem on the first question i had. The carbonyl groups on the product are bonded to the wrong carbons.

[OrgoloathesJess]

I am completely stumped on this question. This is my thought process: I need to find which mechanisms will remove the bromine and add two hydroxyl groups. I think it might go under oxidation/reduction because the end compound has two OH groups. Also, I need to find what synthesis will take the Br away and i cannot find it. There will be two synthesis correct?
Can you tell me if I am going in the right direction or what direction should i take?....any help would be great.

This is the problem:
Propose a synthesis for trans-cyclohexanediol from bromocyclohexane. Indicated the stereochemistry ofter each synthetic step. If a mixture of products, if produced after a particular step, indicate the major product and the minor product.

[UG]

This is my thought process: I need to find which mechanisms will remove the bromine and add two hydroxyl groups.

Do you know of any reagent(s) which will create an alkene from a haloalkane?
From there, do you know what steps can be taken to form a diol from an alkene with anti stereochemistry?

[OrgoloathesJess]

UG.....this is what i have so far.

I know my reagents may or may not be right.

I can use dehydrohalogenation as the eliminating reaction..is that correct?

[UG]

Ok, that looks good 
Do you know about the combination of KOH/ethanol?

[OrgoloathesJess]

No, i dont...the problem im having is that i cant find any elimination reactions on my notes. I looked on wiki and saw that they used koh....can i use that instead?

[OrgoloathesJess]

i can also use KOtBu right?....is my second synthase correct.

[UG]

Yeah the second step is ok. I am sure they won't mind you using KOH/ethanol or other strong bases such as KOtBu.

[OrgoloathesJess]

Okay I have another question for you UG.

This is the problem:
problem #1
Compound A with a molecular formula of C4H6 decolorizes Br2 and produces a precipitate when reacted with permanganate solution. Addition of HCL to A produces two compounds B and C both with the formula C4H7Cl.Ozonolysis of A followed by work-up produces two compounds D and E. Ozonolysis of B followed by work-up produces two products, D and F. Ozonolysis of C followed by work-up produces two products, G and H.

Draw structures for A, B, C, D, E, F, G, and H.

Show the reaction pathway for the formation of each product. Do NOT include the mechanism.

This is the work i have for it:

[UG]

This question is rather tricky because everything is in the first step: the addition of HCl to A.
Because A is a conjugated diene (1,3-butadiene), the addition of HCl to it gives two products, one of which is unexpected. 3-chlorobut-1-ene is the product of 1,2-addition to a double bond (the structure which you have drawn on top). However the second product is actually 1-chlorobut-2-ene. This is described as a 1,4-addition. This product can be explained by the involvement of allylic carbocation intermediates but since you don't need the mechanism, I will not bore you with the details  
Oh yea and you forgot to add a H atom for the structure of F

[OrgoloathesJess]

Okay this is what i have now:

[UG]

Yes that looks good  don't forget the H atoms on your aldehydes.

[mrkitty]

Hi there, I have a problem very (scarily) close to this one.

The question is as follows:

Compound A with a molecular formula of C6H10 decolorizes Br2 and produces a precipitate when reacted with permanganate solution. Hydrogenation with H2 over Pd/C produces B with a formula of C6H12. Reaction of A with peroxyacetic acid produces C, which is highly strained. Hydration of C produces D. Reaction of A with osmium(VIII) oxide followed by work-up produces E which is an isomer of D.  C can also be produced by addition of A to bromine water followed by heating. Ozonolysis of A produces a single product E which is a symmetrical diketone.

Draw structures for A,B,C,D,and E.

This is what I have so far. I am confused because I do not have a mechanism involving heating bromine water. and when I do the ozonolysis of A I do not get the same compound as the E I got from the Os reaction. Any help would be greatly appreciated