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Chapter 12: PROBLEM 12.13 (page 466)

Question: A chiral alkyne A with molecular formula C6H10 is reduced with and Lindlar catalyst to B having the R configuration at its stereogeniccentre. What are the structures of A and B?

Short Answer

Expert verified

Answer

Structure A

Structure B

Step by step solution

01

Stereogenic center

An atom is attached with four different groups such that its mirror image non-superimposable is known as a stereogenic center.

When any two group鈥檚 positions are exchanged, the molecule structure results in enantiomers (two isomers with R and S configuration).

02

Reaction of A with Lindlar catalyst

The triple bond is reduced to a double bond (cis alkene).

Reduction of alkyne to an alkene with stereogenic carbon center

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Most popular questions from this chapter

Question: For alkenes A, B, and C:

Compound A (Monosubstituted)

Compound B (Tetrasubstituted)

Compound C (disubstituted)

(a) Rank A, B, and C in order of increasing heat of hydrogenation;

(b) Rank A, B, and C in order of increasing rate of reaction with H2 Pd-C; (c) Draw the productsformed when each alkene is treated with ozone, followed by Zn-H2O.

Question: Draw the products formed when the following diene is treated with O3followed by H3CSCH3 .

Draw the organic products formed when cyclopentene is treated with each reagent. With some reagents, no reaction occurs.

a. H2+Pd-C

b. H2+ Lindlar catalyst

c. Na ,NH3

d. CH3CO3H

e. [1]. CH3CO3H [2] H2O ,OH-

f. [1] OSO4+NMO [2] NaHSO3, H2O

g.KMnO4 ,H2O ,OH-

h. [1] LiAlH4 [2] H2O

i. [1] O3 .[2] H3CSCH3

j. (CH3)3COOH ,Ti [OCH(CH3)3]4 (-) DET

k. mCPBA

l.Product in (k); Then[1] LiAlH4 [2] H2O

Question: Draw the products formed when A is treated with each reagent: (a) H2 Pd-C; (b) mCPBA; (c) PCC; (d) CrO3, H2SO4, H2O; (e) Sharpless reagent with (+)-DET.

Question: How many rings and 蟺 bonds are contained in compounds A鈥揅? Draw one possible structure for each compound.

a. Compound A has molecular formula C5H8 and is hydrogenated to a compound having molecular formula C5H10.

b. Compound B has molecular formula C10H16 and is hydrogenated to a compound having molecular formula C10H18 .

c. Compound C has molecular formula C8H8 and is hydrogenated to a compound having molecular formula C8H16.
See all solutions

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