3. Let the compound below serve as your starting material, compound A:

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Chapter1: Chemical Foundations
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Q ) c,d,e
3. Let the compound below serve as your starting material,
compound A:
OH
a) Classify the alcohol above (i.e., primary, secondary or
tertiary).
b) Redraw compound A and circle a chiral carbon.
state
c) Draw the products, compounds B and C, and state the
reagent and condition when compound A is dehydrated.
will
d) State, with reason and making reference to Zaitsev's
Rule, which compound, B or C, will be the MAJOR
product.
e) Using the MINOR product, draw the hydration
mechanism to reform compound A.
f) Draw the product, compound D, that will form when
compound A is reacted acidified potassium
permanganate.
a) State the colour changes that will occur when compound
D is reacted with (i) 2,4-DNPH and (ii) Bromine water
(iii) Benedict's reagent (iv)Tollens reagent and (v)
Iodine, NaOH.
(2 Under extreme conditions with acidified potassium
permanganate, it is possible for compound D to be
converted into a mixture of compounds. What type of
compounds would form?
(3 Provide a plausible mechanism for the reaction of
compound D and HCN to form a compound E.
Transcribed Image Text:3. Let the compound below serve as your starting material, compound A: OH a) Classify the alcohol above (i.e., primary, secondary or tertiary). b) Redraw compound A and circle a chiral carbon. state c) Draw the products, compounds B and C, and state the reagent and condition when compound A is dehydrated. will d) State, with reason and making reference to Zaitsev's Rule, which compound, B or C, will be the MAJOR product. e) Using the MINOR product, draw the hydration mechanism to reform compound A. f) Draw the product, compound D, that will form when compound A is reacted acidified potassium permanganate. a) State the colour changes that will occur when compound D is reacted with (i) 2,4-DNPH and (ii) Bromine water (iii) Benedict's reagent (iv)Tollens reagent and (v) Iodine, NaOH. (2 Under extreme conditions with acidified potassium permanganate, it is possible for compound D to be converted into a mixture of compounds. What type of compounds would form? (3 Provide a plausible mechanism for the reaction of compound D and HCN to form a compound E.
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