Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
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Chapter 17.9, Problem 16P
Write the step(s) needed to convert
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Draw the product formed when pentanal (CH;CH,CH2CH;CHO) is treated with each reagent. With some reagents, no reaction
occurs.
a. NaBH4, CH,OH
b. [1] LIAIH4; (2] H20
c. H2, Pd-C
d. PCC
e. NazCr,07, H2SO4, H2O
f. Ag,0, NH,OH
g. [1) CH,MgBr; (2] H2O
h. [1] CęH,Li; [2] H20
i. [1] (CH3),CuLi; (2] H2O
j. [1] HC=CNa; [2] H2O
k. [1] CH;C=CLi; [2] H2O
I. The product in (a), then TBDMS-CI, imidazole
What is the major product of each of the following reactions?
What is the structure of compound A?
010
Compound A
tot
01
Oll
O III
O IV
OV
||
s
|||
Compound A
IV
COOH
Chapter 17 Solutions
Organic Chemistry (6th Edition)
Ch. 17.1 - Prob. 1PCh. 17.2 - Which carbonyl groups in the anticancer drug taxol...Ch. 17.2 - Prob. 3PCh. 17.4 - Problem 20.4 What alcohol is formed when each...Ch. 17.4 - Problem 20.5 What aldehyde or ketone is needed to...Ch. 17.5 - Problem 20.8 Draw the products formed (including...Ch. 17.7 - Problem 20.10 Draw a stepwise mechanism for the...Ch. 17.7 - Prob. 10PCh. 17.7 - Problem 20.12 Draw the products formed from ...Ch. 17.7 - Prob. 12P
Ch. 17.7 - Prob. 13PCh. 17.8 - Prob. 14PCh. 17.8 - Problem-20.16 Review the oxidation reactions using...Ch. 17.9 - Problem-20.17 Write the step(s) needed to convert ...Ch. 17.9 - Prob. 18PCh. 17.10 - Problem 20.21 Draw the product of each reaction.
...Ch. 17.10 - Problem 20.22 Draw the products (including...Ch. 17.11 - Problem 20.23 What Grignard reagent and carbonyl...Ch. 17.11 - Problem 20.24 Linalool (the Chapter 9 opening...Ch. 17.11 - Problem 20.25 What Grignard reagent and carbonyl...Ch. 17.12 - Prob. 24PCh. 17.13 - Problem 20.28 What ester and Grignard reagent are...Ch. 17.13 - Prob. 27PCh. 17.13 - Problem 20.30 What reagent is needed to convert ...Ch. 17.13 - Prob. 29PCh. 17.14 - What carboxylic acid formed from each alkyl halide...Ch. 17 - 20.37 Devise a synthesis of each alcohol from...Ch. 17 - 20.38 Draw the products formed when pentanal is...Ch. 17 - 20.39 Draw the product formed when is treated...Ch. 17 - The stereochemistry of the products of reduction...Ch. 17 - Prob. 40PCh. 17 - 20.42 Draw the products or each reduction...Ch. 17 - 20.44 Draw all stereoisomers formed in each...Ch. 17 - 20.54 Draw a stepwise mechanism for the following...Ch. 17 - Prob. 57PCh. 17 - Prob. 58PCh. 17 - 20.57 What ester and Grignard reagent are needed...Ch. 17 - 20.58 What organolithium reagent and carbonyl...Ch. 17 - 20.59 What epoxide and organometallic reagent are...Ch. 17 - Prob. 62PCh. 17 - 20.69 An unknown compound A (molecular formula )...Ch. 17 - 20.70 Treatment of compound C (molecular formula )...
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- Draw the products in each reaction.arrow_forwardWhich is a thiol? CH3 HS SH b. HO. CH3 H.CS CHa CH C. H. d. భిగింగడి 工 a.arrow_forwardDraw the product formed when phenylacetaldehyde (CsH;CH,CHO) is treated with each reagent. Phenylacetaldehyde is partly responsible for the fragrance of the flowers of the plumeria tree, which is native to the tropical and subtropical Americas. e. Ph;P=CHCH3 f. (CH),CHNH2, mild acid g. (CH,CH)NH, mild acid h. CH,CH,OH (еxсess), H' а. NaBHa, CH,Oн b. [1] LIAIH4; (2] H20 c. [1] CH;MgBr; [2] H2O i. NH, mild acid d. NaCN, HCI j. HOCH,CH;OH, H*arrow_forward
- Draw the products formed when each alcohol is dehydrated with H 2SO 4. Use the Zaitsev rule to predict the major product when a mixture forms.arrow_forwardWhat carbonyl compound is needed to make each alcohol by a reduction reaction? What carbonyl compound is needed to make each alcohol by a reduction reaction?arrow_forward3. What product is formed when HO(CH₂) CHO is treated with each reagent? c. Ag₂O, NH OH d. Na₂Cr₂O₂, H₂SO4, H₂O a. NaBH, CH₂OH b. PCC 400arrow_forward
- Draw the products formed when p-methylaniline (p-CH3C6H4NH2) is treated with each reagent. a. HCl b. CH3COCl c. (CH3CO)2O d. excess CH3I e. (CH3)2C = O f. CH3COCl, AlCl3 g. CH3CO2H h. NaNO2, HCl i. Part (b), then CH3COCl, AlCl j. CH3CHO, NaBH3CNarrow_forwardDraw the product formed when phenylacetic acid (C6H5CH2COOH) is treated with each reagent. With some reagents, no reaction occurs. a. NaHCO3 b. NaOH c. SOCl2 d. NaCl e. NH3(1equiv) f. NH3, ∆ g. CH3OH, H2SO4 h. CH3OH, −OH i. [1] NaOH; [2] CH3COCl j. CH3NH2, DCC k. [1] SOCl2; [2] CH3CH2CH2NH2 (excess) l. [1] SOCl2; [2] (CH3)2; [2] (CHarrow_forwardDraw the products formed when each compound is treated with CH;CH,COCI, AICI3. CH(CH3)2 N(CH)2 Br CH3 CH(CH)2 a. b. C. d. е.arrow_forward
- What is the major organic product obtained from the following reaction? A. CI B. H 1. (CH3CH₂)2CuLi 2. H3O+ C. D. •ay.a OHarrow_forwardWhat alkenes are formed when each alcohol is dehydrated with TSOH? Label the major product when a mixture results. OH Xom OH a. OH b. CH₂CH3 OH C. d. CH₂CH₂CH₂CH₂OH e.arrow_forwardDraw the products formed when each alcohol is dehydrated with H 2SO 4. Use the Zaitsev rule to predict the major product when a mixture forms.arrow_forward
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