13.9 Alcohol Synthesis Problems

Extra Problems

7. Draw the following compounds: a) isopropyl magnesium bromide b) 3-heptanol c) cyclohexanol d) 4-iodophenol e) 3-cyclopenten-1-ol f) p-chlorophenol g) (R)-pentane-1,4-diol h) cyclohexane-1,2,3-triol i) o-bromophenol j) propylene glycol k) (Z)-4-chloro-3-buten-2-ol l) 2-methylbut-3-yn-1-ol m) m-cresol n) cyclohexylmethanol o) 4-bromobutan-1-ol p) propyl mercaptan q) pentanethiol r) butyl mercaptan s) butane-2-thiol

8. Name the following compounds:

a)

b)

c)

d)

e)

f)

g)

h)

i)

j)

k)

l)

9. A little chemistry joke. . . What words do the following structures represent? Think ortho, meta, and para.

10. Which of the following IR spectra is that of an alcohol?

11. The following alcohol can be synthesized from two different alkenes. Draw these two alkenes and then give the reagents you would use to synthesize the alcohol from each of these alkenes.

12. Draw the products of the following reactions. a) 1-methylcyclopentene + dilute aqueous acid b) 1-methylcyclopentene + aqueous Hg(OAc)₂ followed by NaBH₄ c) 1-methylcyclopentene + a cold, dilute, neutral solution of potassium permanganate d) 1-methylcyclopentene + BH₃.THF followed by H₂O₂ and NaOH e) 1-methylcyclopentene + OsO₄ followed by H₂O₂ f) 1-methylcyclopentene + peroxybenzoic acid in water g) 2-methylpropene + aqueous Hg(OAc)₂ followed by NaBH₄ h) 2-methylpropene + dilute aqueous H₂SO₄ i) 2-methylpropene + BH₃.THF followed by H₂O₂ and NaOH j) 2-methylpropene + OsO₄ followed by H₂O₂ k) 2-methylpropene + MCPBA followed by acid/water l) cyclopentene + peroxybenzoic acid in water m) cyclopentene + a cold, dilute, neutral solution of potassium permanganate n) cyclopentene + OsO₄ followed by H₂O₂ o) cyclopentene + MCPBA followed by acid/water

13. Show how you would prepare the following compounds starting with an alkene and any other reagents you need. a) 1-heptanol b) 2-heptanol c) 1-ethyl-1-cyclopentanol d) 2-ethyl-1-cyclopentanol

14. How could you make 2-methylcyclopentanol from 1-bromo-1-methylcyclopentane? More than one reaction is required.

15. Determine what aldehyde, ketone, or epoxide would react with ethyl magnesium bromide such that, upon quenching with aqueous acid, would make the following compounds.

a)

b)

c)

d)

e)

f)

g)

h)

16. Determine an appropriate Grignard reagent that would react with acetaldehyde (CH₃CHO) such that, upon quenching with aqueous acid, would make the following compounds.

a)

b)

c)

d)

e)

17. Determine an appropriate Grignard reagent that would react with 1,2-epoxypropane such that, upon quenching with aqueous acid, would make the following compounds.

a)

b)

c)

d)

e)

18. Draw the structure of an acid chloride that would react with an excess of methyl magnesium bromide such that, upon quenching with aqueous acid, would make the following compounds. Then, draw an appropriate ester for each problem that you could use instead of the acid chloride.

a)

b)

c)

d)

e)

19. Give two ways you could synthesize the following compounds using the reaction of a Grignard reagent and an aldehyde.

a)

b)

c)

d)

20. Give three ways you could synthesize the following compounds using the reaction of a Grignard reagent and a ketone.

a)

b)

c)

d)

21. For each of the following compounds, show how it could be synthesized from an acid chloride or ester and an excess of a Grignard reagent.

a)

b)

c)

d)

22. Reducing a carbonyl compound can make the following compounds. Show what carbonyl compound and appropriate reducing agent can be used to make each of the following.

a)

b)

c)

d)

e)

23. Draw the products for each of the following reactions.

a)

b)

c)

d)

e)

f)

g)

h)

i)

j)

k)

l)

m)

n)

o)

p)

q) H₂C=CHCO₂H + 1) LiAlH₄, 2) acid/water r) CH₃CH₂COCl + 1) LiAlH₄, 2) acid/water s) CH₃CO₂CH₂CH₂CHO + 1) NaBH₄, 2) acid/watert) CH₃COCH₂CH=CHCH₂CO₂CH₃ + 1) LiAlH₄, 2) acid/water u) PhCH₂CHO + 1) LAH, 2) acid/water v) iodohexane + sodium hydrosulfide

24. What reagents are needed to perform the following transformations? a) CH₃CO₂CH₂CH₂CHO to CH₃CO₂CH₂CH₂CH₂OHb) CH₃CH₂CO₂H to CH₃CH₂CH₂OHc) CH₃CH₂CH=CHCH₂CHO to CH₃CH₂CH₂CH₂CH₂CH₂OH d) CH₃CO₂CH₃ to CH₃CH₂OH e)

f)

g)

h)

i)

j)

k)

l)

m)

n)

o)

p)

q) CH₃CH₂CH₂CO₂H to CH₃CH₂CH₂CH₂OH r) PhCO₂Cl to Ph₃COH s) PhCO₂Cl to PhCH₂OH t) HCO₂CH₂CH₃ to (Ph)₂CHOH u) 1,2-epoxybutane to 3-hexanol v) PhCH₂Cl to PhCH₂CH₂OH w) 1-bromobutane to 1-pentanol x) EtCO₂CH₃ to (Et)₃COH y) 1-bromocyclopentane to 1-cyclopentyloctane z) propene to propylene glycol aa) bromobenzene to 2-phenylethanol bb) bromopentane to pentanethiol

25. A mixture of ortho, meta, and para aromatic compounds is below.

a) Label A, B, and C as ortho-, meta-, or para-. b) What would be the product of the reaction of A with an excess of NaBH₄ followed by hydrolysis? c) What would be the product of the reaction of C with an excess of LiAlH₄ followed by hydrolysis? d) Draw the product and the mechanism of the reaction of B with an excess of ethyl grignard (CH₃CH₂MgBr) followed by hydrolysis.

26. The following reactions did not work as planned. What is wrong with each of these reactions?

a)

b)

c)

d)