1) The document provides information about NMR spectroscopy, functional group identification using chemical tests, and organic reactions. 2) Key information includes the expected splitting patterns for 1-propanol in NMR, that a compound giving an orange precipitate with 2,4-DNP indicates an aldehyde or ketone, and how carboxylic acids, alcohols, and amines react to form esters, acid chlorides, and amides respectively. 3) Multiple choice questions are included about identifying functional groups from spectral data and predicting products of organic reactions.

1. H NMR signal for which of the indicated16. The H-NMR of 1-propanol. What is the expected
occurs farthest downfield protons A)i B) II C)III D)IV splitting pattern for each signal in the
order fa, b,cd Ci H A) triplet, doublet, triplet, singlet B) doublet, quartet, sextet, octet C) triplet,
sextet, triplet, singlet 11, A compound shows an orange ppt. when treated with 2,4-DNP reagent.
What can we conclude from this result? D) triplet, doublet, doublet, singlet 17 For trans-1,2-
dichloroethene, what would the A) The compound is a methyl ketone B) The compound is a
carboxylic acid C) The compound is an aldehyde or ketone D) None of the above splitting
pattern be for the protons? A) Two Doublet of Doublets 8)One doublet C) Two Singlets D) One
Singlet For questions 18-20 refer the to the following. 12. What chemical test can be used to
distinguish between the following compounds? A) Chromic acid test B) Tollen's test C)
Hinsberg test D) Lucas test OH which ofthe f_grepresentsproduct F? 13. The IR spectrum of
compound P shows a broad peak at 3300cm 1. What functional group is present? A) Amide B)
Ester C)Alcohol D) Ketone 14, The IR absorption due to the stretching of which of these C-H
bonds occurs at the highest frequency? 19, The structure for compound G is 20. Which is formed
if compound F is reacted with 15, A compound with the molecular formula CoH,Cl, Methanol?
gave a 'HNMR spectrum consisting only of a triplet centered at 3.7ppm and a quintet centered at
2.2 ppm. The most likely structure for the compound is E) CH CCI,CH D) CICH CH2CH CI
Solution
10.
Answer is option E.
Aromatic protons appears at down field at above 7 ppm.
11.
Answer is option C.
2,4-Dinitrophenylhydrazine is the chemical compound C?H?(NO?)?NHNH?.
Dinitrophenylhydrazine is a red to orange solid. It is a substituted hydrazine, and is often used to
qualitatively test for carbonyl groups associated with aldehydes and ketones.
12.

2. Answer is option A.
Chromic acid oxidizes primary alcohol.
13.
Answer is option A.
-OH group of alcohol appears at3300 cm -1
.
14.
Answer is option C.
?C-H stretch appears at highest frequency.
15.
Answer is option A.
There are two types of protons.
18.
Answer is option D.
When carboxylic acid reacts with thionyl chloride it produces acid chloride.
19.
Answer is option A.
When acid chloride reacts with NH3 it produces amide.
20.
Answer is option D.
When acid chloride reacts with alcohol it produces an ester.