Solved Problems on Functional Group Synthesis

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Chapter: Organic Chemistry : Functional Group Synthesis

Questions and answers, Solved Problems on Functional Group Synthesis - Organic Chemistry



7.1. Show how you would prepare each of the following products from the given starting material. For each overall transformation indicate (1) the starting and ending functional group and (2) what change in oxidation level (if any) must be accomplished. Where more than one step is required, show each step distinctly, including reagents and conditions needed to effect the conversion


(a) 1 Alcohol aldehyde, [O] = +2, PCC or Swern oxidation

(b) Ester ether, [H] = −4

i. LAH

ii. NaH, CH3l

(c) Acid amide, no change

i. SOCl2, DMF




(d) Ketone methylene compound, +2 0 [H]

i. Ph3P=CH2 (Wittig) or Me3SiCH2-Li (Peterson)

(e) 1 Alcohol aldehyde, 1 → +1, PCC or Swern oxidation

(f) Lactone lactol (hemiacetal); +3 → +1; DIBAH, toluene, 78

(g) 2 Alcohol 2 amine, no change

i. H2CrO4, acetone

ii. CH3NH3, NaBH3CN, H+

(h) Acid ester, +3 → +3

i. DCC, Et3N, EtOH


i. oxallyl chloride

ii. EtOH, py

(i) Alkene alcohol; 0, 2 → +1, 3 no change

i. HgOAc2, H2O

ii. NaBH4

(j) Alkene alcohol; 1, 2 → −2, 1 no change


ii. NaOH, H2O2

(k) Ketone alcohol + cyclization, +2 0 [O]

i. NaBH4

ii. TsOH, benzene,

(l) Ketone acetal; no change; HOCH2CH2CH2OH, TsOH, toluene,

(m) Acid alcohol acetylation, +3 → −1 [H]

i. BH3-THF

ii. Ac2O, py, DMAP

(n) Alkene alcohol, no change

i. HgOAc2, H2O

ii. NaBH4, MeOH

(o) Ketone α, β -unsaturated ketone; 2, 3, → −1, 2, [O]

i. LDA

ii. PhSeSePh

iii. H2O2


i. pyH+ Br3

ii. K2CO3

(p) 2 Alcohol acetal, 0 → +2, [O]

i. H2CrO4

ii. CH3OH, H+, Δ

(q) trans-Alkene alkyne; 1, 1 0, 0 [O]

i. Br2, CCl4

ii. NaNH2


(s) Acid amide, no change

i. DCC, Et3N, NH2R


i. oxallyl chloride,

ii. NH2R

(t) Alcohol ester, no change

i. ClCH2CH2C(O)Cl, py

(u) Alkene alcohol, no change

i. BH3 –THF

ii. NaOH, H2O2

(v) Alkyl bromide alkene, [H]

i. NaC2H

ii. BuLi

iii. PrBr

iv. H2, P-2 Ni


7.2. Show two different starting materials from which you could obtain each of the following compounds. Show the reagents and conditions necessary to convert each of the starting materials into the desired product.



7.3. Give the final products of the following reaction sequences and show the intermediate products as well. If mixtures are expected, indicate which will be the major product.


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