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Oxidation and Structure of Limonene

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Limonene, C10H16, a terpene found in citrus peel, absorbs only two moles of hydrogen forming p-menthane C10H20. Oxidation by permanganate converts limonene into structure A in the attached .jpg (ignore structures B and C for this problem).

1. How many rings, if any, are in limonene?

2. What structures are consistent with the oxidation products?

3. On the basis of the isoprene rule, which structure is most likely for limonene? For p-menthane?

4. Addition of 1 mole H2O converts limonene into an alcohol. What are the most likely structures for this alcohol?

5. Addition of two moles of H2O to limonene yields terpin hydrate. What is the most likely structure for terpin hydrate?

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This solution addresses 5 questions on the oxidation of Limonene

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Natural Products - Limonene

I am having a little trouble with finishing this problem

Question: Limonene, C10H16, a terpene product found in orange, lemon, and grapefruit peel, absorbs only two molecules of hydrogen, forming p-methane, C10H20. Oxidation by permanganate converts limonene into VIII.

a) How many rings if any are in the limonene
Well from finding the structure I was able to determine that it consists of one ring.

b)What structures are consistent with the oxidation product
I am having trouble figuring this one out I have a structure but don't know how to put it in on the computer.

c) One the basis of the isoprene rule, which structure is most likely for limonene?

This should be correct right?

For p-methane
Now I tried to deduce this structure and I even tried looking in the textbook to help me but my structures are not coming out correctly.

d) Addition of one mole of water converts limonene into an alcohol. What are the most likely structures for this alcohol?

Since I can't draw it I will describe what I think it should be. One structure could be where the double bond in the ring (closest to the methyl group) is hydrolyzed and an OH is added to the one of the carbons that contained the now broken double bond. The second structure has OH added to the second double bond not contained in the ring.

e) Addition of two moles of water to limonene yields terpin hydrate. What is the most likely structure for terpin hydrate?

I have no clue what a terpin hydrate is?

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