extra final prep

Question 1

what reagents can be used to produce an alkane from any alcohol (3 steps)

Answer 1

1. HBr, HI, HCl + ZnCl2, SOCl2, PBr3, or PCl5
2. Mg in ether
3. dilute H3O+

Question 2

what reagents can be used to produce an alkane from a 1° or 2° alcohol (2 pathways, each 2 steps)

Answer 2

1.ArSO3Cl in pyridine
2.LiAlH4 in ether followed by H3O+

1.HBr, HI, HCl + ZnCl2, SOCl2, PBr3, or PCl5
2.LiAlH4 in ether followed by H3O+

Question 3

what reagents are needed to produce an alkyl halide from any alcohol?

Answer 3

HBr, HI, HCl + ZnCl2, SOCl2, PBr3, or PCl5

Question 4

what reagents are needed to produce alkenes from alcohols?

Answer 4

H2SO4 or H3PO4 and heat

Question 5

what reagents are needed to produce alcohols from alkenes (2 pathways)?

Answer 5

1. Hg(OAc)2 in H2O followed by NaBH4 in ethanol
2. B2H6 in ether followed by H2O2 in NaOH

Question 6

what reagents will produce alcohols from carboxylic acids?

Answer 6

LiAlH4 in ether followed by H3O+

Question 7

what reactants will produce carboxylic acids from 1° alcohols?

Answer 7

Na2Cr2O7 in H2SO4

Question 8

what reagents will produce alcohols from ketones (2 pathways)?

Answer 8

1. LiAlH4 in ether followed by H3O+
2. NaBH4 in ethanol

Question 9

what reagents will produce ketones from any alcohol?

Answer 9

PCC (CrO3 + pyridine + HCl in CH2Cl2 solution)

Question 10

what reagents will produce ketones from 2° alcohols?

Answer 10

Na2Cr2O7 in H2SO4

Question 11

what reagents will produce alcohols from aldehydes (2 pathways)?

Answer 11

1. LiAlH4 in ether followed by H3O+
2. NaBH4 in ethanol

Question 12

what reagents will produce aldehydes from 1° alcohols?

Answer 12

PCC (CrO3 + pyridine + HCl in CH2Cl2 solution)

Question 13

what reagents will produce sulfonate esters from alcohols?

Answer 13

ArSO3Cl in pyridine

Question 14

what reagents will produce alcohols from carboxylate esters (2 pathways)?

Answer 14

1. LiAlH4 in ether followed by H3O+
2. refluxing NaOH solution

Question 15

what reagents will produce carboxylate esters from any alcohols (2 pathways)?

Answer 15

1. heating with COOH and a strong acid catalyst
2. carboxylic acid anhydride or acyl chloride in pyridine

Question 16

what reagents will produce ethers from any alcohols (2 pathways)?

Answer 16

1. Na or NaH in ether
2. 1° alkyl halide or tosylate (R-X)

Question 17

what products will alkynes reacted in H2 / Pd0 give?

Answer 17

alkanes

Question 18

what reagents would you use to produce an alkane from an alkyne?

Answer 18

H2 / Pd0

Question 19

what reagents will produce cis alkenes from alkynes?

Answer 19

H2 / lindlar’s catalyst

Question 20

what will be the product of an alkyne reacted with H2 / lindlar’s catalyst?

Answer 20

a cis alkene

Question 21

what will be the product of an alkyne reacted in Na/NH3?

Answer 21

a trans alkene

Question 22

what reagents will produce a trans alkene from an alkyne?

Answer 22

Na/NH3

Question 23

what reagents will produce an aldehyde from a terminal alkyne?

Answer 23

1. (sia)2BH.THF
2. H2O2, NaOH