Extra Problems
7. Draw the following compounds:a) isopropyl magnesium bromideb) 3-heptanolc) cyclohexanold) 4-iodophenole) 3-cyclopenten-1-olf) p-chlorophenolg) (R)-pentane-1,4-diolh) cyclohexane-1,2,3-trioli) o-bromophenolj) propylene glycolk) (Z)-4-chloro-3-buten-2-oll) 2-methylbut-3-yn-1-olm) m-cresoln) cyclohexylmethanolo) 4-bromobutan-1-olp) propyl mercaptanq) pentanethiolr) butyl mercaptans) 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 acidb) 1-methylcyclopentene + aqueous Hg(OAc)2 followed by NaBH4c) 1-methylcyclopentene + a cold, dilute, neutral solution of potassium permanganated) 1-methylcyclopentene + BH3.THF followed by H2O2 and NaOHe) 1-methylcyclopentene + OsO4 followed by H2O2f) 1-methylcyclopentene + peroxybenzoic acid in waterg) 2-methylpropene + aqueous Hg(OAc)2 followed by NaBH4h) 2-methylpropene + dilute aqueous H2SO4i) 2-methylpropene + BH3.THF followed by H2O2 and NaOHj) 2-methylpropene + OsO4 followed by H2O2k) 2-methylpropene + MCPBA followed by acid/waterl) cyclopentene + peroxybenzoic acid in waterm) cyclopentene + a cold, dilute, neutral solution of potassium permanganaten) cyclopentene + OsO4 followed by H2O2o) 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-heptanolb) 2-heptanolc) 1-ethyl-1-cyclopentanold) 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.
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/waterr) CH3CH2COCl + 1) LiAlH4, 2) acid/waters) CH3CO2CH2CH2CHO + 1) NaBH4, 2) acid/watert) CH3COCH2CH=CHCH2CO2CH3 + 1) LiAlH4, 2) acid/wateru) PhCH2CHO + 1) LAH, 2) acid/waterv) iodohexane + sodium hydrosulfide
24. What reagents are needed to perform the following transformations?a) CH3CO2CH2CH2CHO to CH3CO2CH2CH2CH2OHb) CH3CH2CO2H to CH3CH2CH2OHc) CH3CH2CH=CHCH2CHO to CH3CH2CH2CH2CH2CH2OHd) CH3CO2CH3 to CH3CH2OHe)
f)
g)
h)
i)
j)
k)
l)
m)
n)
o)
p)
q) CH3CH2CH2CO2H to CH3CH2CH2CH2OHr) PhCO2Cl to Ph3COHs) PhCO2Cl to PhCH2OHt) HCO2CH2CH3 to (Ph)2CHOHu) 1,2-epoxybutane to 3-hexanolv) PhCH2Cl to PhCH2CH2OHw) 1-bromobutane to 1-pentanolx) EtCO2CH3 to (Et)3COHy) 1-bromocyclopentane to 1-cyclopentyloctanez) propene to propylene glycolaa) bromobenzene to 2-phenylethanolbb) 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)
