Chemistry $^{3}$ : Introducing inorganic, organic and physical chemistry

Andrew Burrows, John Holman, Andrew Parsons

Chapter 2 The language of organic chemistry - all with Video Answers

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Chapter Questions

03:15

Problem 1

Draw skeletal structures of the following compounds: (a) 2,3,5-trimethylhexane;
(b) 5-ethyl-6-isopropyl-3-methyinonane. (Section 2.5)

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01:48

Problem 2

Draw skeletal structures and give the names of the five structural isomers of the hydrocarbon with molecular formula $\mathrm{C}_{6} \mathrm{H}_{14}$. (Section 2.5)

Grigoriy S.

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03:14

Draw skeletal structures of the following compounds (Sections $2.6$ and $2.7$ ):
(a) $\mathrm{PhCH}(\mathrm{OH}) \mathrm{CH}_{2} \mathrm{CH}\left(\mathrm{NH}_{2}\right) \mathrm{CH}_{3}$;
(b) $\mathrm{EtCOCH}(\mathrm{Me}) \mathrm{CO}_{2} \mathrm{Me} ;$
(c) $\mathrm{Me}_{2} \mathrm{C}=\mathrm{CHCH}_{2} \mathrm{CH}_{2} \mathrm{C}\left(\mathrm{CH}_{3}\right)=\mathrm{CHCH}_{2} \mathrm{OH}$;
(d) 5-(3-nitrophenyl)-5-oxopentanoic acid.

Grigoriy S.

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01:43

Problem 4

Name all of the functional groups in the following molecules. (Sections $2.6$ and 2.7)

Grigoriy S.

Numerade Educator

Problem 5

Give IUPAC names for the following compounds (Section 2.8):
(a) $\mathrm{Br} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CHMe}_{2}$;
(b) $\mathrm{H}_{2} \mathrm{C}=\mathrm{CHCH}_{2} \mathrm{OH}$;
(c) $\mathrm{H}_{2} \mathrm{NCH}_{2} \mathrm{CH}_{2} \mathrm{CO}_{2} \mathrm{Me}$.

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04:16

Problem 6

The following questions relate to the synthesis of the local anaesthetic ambucaine, starting from 3-hydroxybenzoic acid, which is shown in the scheme below. (Sections 2.2-2.8) (a) Is 3-hydroxybenzoic acid an ortho-, meta-, or para- disubstituted benzene?
(b) Draw skeletal structures for compounds 1 and 3 .
(c) Give the IUPAC names for compounds 2 and 4 .
(d) Name all of the functional groups in compound 5 .
(e) Given that the $-\mathrm{NO}_{2}$ group of compound 5 is reduced to $\mathrm{an}-\mathrm{NH}_{2}$ group, on reaction with $\mathrm{H}_{2}$ and Ni (catalyst), draw a skeletal structure for ambucaine.

Grigoriy S.

Numerade Educator

04:17

Problem 7

The hot spicy flavour of chilli peppers of the Capsicum family is due mainly to a compound called capsaicin. The following questions relate to the synthesis of capsaicin shown below. (Sections 2.2-2.8) (a) Draw a skeletal structure of the stereoisomer of alkene $6 .$
(b) In compound 7 , is the bromine bonded to a primary, secondary, or tertiary carbon atom?
(c) For the synthesis of compound 8, $\mathrm{NaCH}\left(\mathrm{CO}_{2} \mathrm{Et}\right)_{2}$ is prepared from $\mathrm{CH}_{2}\left(\mathrm{CO}_{2} \mathrm{Et}\right)_{2}$, which has the common name diethyl malonate. Draw a skeletal structure of diethyl malonate and give the IUPAC name.
(d) Draw the structure of compound 8 and indicate the $\alpha$ and $\beta$ carbon atoms.
(e) Give the IUPAC name for compound $10 .$
(f) Name all of the functional groups in capsaicin.

Grigoriy S.

Numerade Educator

Problem 8

Omeprazole is a medicine, first marketed by AstraZeneca, to treat heartburn, acid indigestion, and ulcers in the stomach. The following questions relate to the synthesis of omeprazole shown below. (Sections 2.5-2.8) (a) Is the alcohol in compound 11 a primary, secondary, or tertiary alcohol?
(b) Reaction of 11 with $\mathrm{SOCl}_{2}$, to give 12 , requires a solvent such as toluene. Draw a skeletal structure for toluene.
(c) What is the name of the heterocyclic aromatic ring in compound $11 ?$
(d) Give the IUPAC name for compound 12 .
(e) What is the name of the functional group in compound 13, that reacts with 12 , to form $14 ?$
(f) The abbreviation mCPBA stands for meta-chloroperbenzoic acid. What does the name 'meta-' indicate?
(g) Reaction of 14 with $m$ CPBA leads to oxidation of the thioether (sulfide) to give a sulfoxide. Draw a skeletal structure for omeprazole.

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