Four isomers A-D with the formula C5H12O exhibit different reactivity patterns as indicated below. Isomer A reacts with PCC and CrO3 to provide identical products. Isomer B reacts with PCC and CrO3 to provide different products. Isomers C and D do not react with either PCC or CrO3
Four isomers A-D with the formula C5H12O exhibit different reactivity patterns as indicated below.
Isomer A reacts with PCC and CrO3 to provide identical products.
Isomer B reacts with PCC and CrO3 to provide different products.
Isomers C and D do not react with either PCC or CrO3.
Isomers A, B, and C readily react with NaH but D does not show any reactivity with NaH.
The 1H NMR splitting patterns for these isomers are as follows.
Isomer A: δ 0.91 (d, 3H), 0.90 (d, 3H), 1.18 (d, 3H), 1.92 (dqq, 1H), 3.38 (dq, 1H), 3.58 (bs, 1H).
Isomer B: δ 1.25 (s, 9H), 3.45 (s, 2H), 3.65 (bs, 1H).
Isomer C: δ 0.90 (t, 3H), 1.44 (q, 2H), 1.24 (s, 6H), 3.65 (bs, 1H).
Isomer D: δ 1.10 (t, 3H), 1.13 (d, 6H), 3.19 (septet, 1H), 3.50 (q, 2H).
Based on all of this information, provide the structures of A-D. (Note: If there is a chiral center on any of these molecules, assume the stereochemistry as “R”. dqq=doublet of a quartet of a quartet, bs=broad singlet)
We have to determine the structure of isomer A,B,C,D.
Trending now
This is a popular solution!
Step by step
Solved in 6 steps with 4 images
