Q80 · CSIR-NET Chemistry, December 2014
Paper: CSIR-NET December 2014 · Subject: Organic Chemistry · Chapter: Organic Spectroscopy · Topic: NMR 1H · Marks: 2 · Difficulty: Hard
The following reactions give a product (racemic) which exhibits the following NMR data: ${ }^{\mathrm{1}} \mathrm{H ~ NMR}: \delta 2.67(\mathrm{2H}, \mathrm{s}), \mathrm{5 . 60}(\mathrm{2H}, \mathrm{s}) ~ p p m ;{ }^{\mathrm{13}} \mathrm{C} ~ N M R: \delta \mathrm{170 . 3}, \mathrm{129 . 0}, 1 0 5 . 0 , 2 5 . 4 ~ p p m$ The structure of the product (racemic) is
(a)
(b)
(c)
(d)
Answer
Answer: C ✓ checked by 4AB · confidence high
Explanation
Feist's acid, trans-3-methylenecyclopropane-1,2-dicarboxylic acid, fits the data. It shows 2 ring CH (δ 2.67, s) and =CH₂ (δ 5.60, s), with ¹³C 170 (COOH), 129 (C=), 105 (=CH₂) and 25 (CH). The trans isomer is chiral, hence racemic (c).
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