ORGANIC CHEMISTRY BOOK& SG/SM
ORGANIC CHEMISTRY BOOK& SG/SM
6th Edition
ISBN: 9781264094493
Author: SMITH
Publisher: MCG
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Chapter 29.2, Problem 1P

One component of jojoba oil is a wax formed from eicosenoic acid [ CH 3 ( CH 2 ) 7 CH = CH ( CH 2 ) 9 CO 2 H ] and CH 3 ( CH 2 ) 7 CH = CH ( CH 2 ) 8 OH . Draw the structure of the wax, including the cis geometry of both carbon–carbon double bonds.

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Draw a Lewis structure for each of the following molecules and assign charges where appropriate. The order in which the atoms are connected is given in parentheses. a. CIFCIF b. BrCNBrCN 0 c. SOCI2 × (CISCIO) SOC₁₂ (CISCI) You can draw both an octet and a valence shell expanded structure. Considering the following structural information, which is the better one: The measured S-OS-O bond length in SOC12SOCl2 is 1.43 Å. For comparison, that in SO2SO2 is 1.43 Å [Exercise 1-9, part (b)], that in CHзSOHCH3 SOH d. CH3NH2CH3NH2 (methanesulfenic acid) is 1.66 A. e. CH3OCH3 CH3 OCH3 NH2 f. N2H2× (HNNH) N2 H2 (HNNH) g. CH2COCH₂ CO h. HN3× (HNNN) HN3 (HNNN) i. N20 × (NNO) N2O (NNO)
bre The reaction sequence shown in Scheme 5 demonstrates the synthesis of a substituted benzene derivative Q. wolsd works 2 NH2 NaNO2, HCI (apexe) 13× (1 HNO3, H2SO4 C6H5CIN2 0°C HOTE CHINO₂ N O *O₂H ( PO Q Я Scheme 5 2 bag abouoqmics to sounde odi WEIC (i) Draw the structure of intermediate O. [2 marks] to noitsmot od: tot meinedogm, noit so oft listsb ni zaupaib bas wa (ii) Draw the mechanism for the transformation of aniline N to intermediate O. Spoilage (b) [6 marks] (iii) Identify the reagent X used to convert compound O to the iodinated compound [tom E P. vueimado oilovonsa ni moitos nolisbnolov ayd toes ai tedw nisiqx (iv) Identify the possible structures of compound Q. [2 marks] [2 marks] [shom 2] (v) bus noires goiribbeolovo xnivollot adj to subora sidab Draw the mechanism for the transformation of intermediate P to compound Q. [5 marks] vi (vi) Account for the regiochemical outcome observed in the reaction forming compound Q. [3 marks]
PROBLEM 4 Solved Show how 1-butanol can be converted into the following compounds: a. PROBLEM 5+ b. d. -C= N
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